1. » Exploiting marine natural products – antifouling polymer coatings
  2. » Marine chemical ecology
  3. » New Zealand fungi as sources of new antibacterial lead compounds
  4. » Structure-activity relationship of new antimalarials
  5. » Structure-activity relationship of new anti-tuberculosis agents
  6. » Structure-activity relationship of polyamine-based antimalarials
  7. » Sulfur compounds profiling in selected yeast strain fermentations
  8. » Bioanalytical Mode-of-Action Studies of Metal-based Anticancer Agents
  9. » Bioorganometallic Anticancer Chemotherapeutics: Preparation of Metal Complexes with Bioactive Ligands
  10. » Design and Applications of Organometallic Complexes for Catalysis
  11. » Design of Multimodal Organometallic Anticancer Agents
  12. » Thermal stability analysis of bioactive compounds from Centella asiatica
  13. » Exploring the effect of fluorination on Claisen rearrangement reactions
  14. » Synthesis of biologically active lignan natural products
  15. » Understanding the biogenesis of H2S in yeast and its role cell signaling
  16. » Synthesis of novel polymeric materials as surface active antimicrobial agents
  17. » Synthesis of novel polymeric materials for modern electronic materials
  18. » Synthesis of Novel inhibitors of Phospholipase C, an enzyme involved in cancer cell proliferation
  19. » Killing surface bacteria
  20. » Making better biominerals
  21. » Catalytic routes to robust polysilanes
  22. » Understanding the mechanism of the copper-catalysed oxidative cross-coupling of amines and phosphates to form phosphoramidates
  23. » Using catalysis to create new bioerodible materials useful in the construction of synthetic bone
  24. » Behaviour of fingermarks on ice
  25. » Hyperspectral imaging in chemical analysis
  26. » Production and purification of recombinant bacterial and human trimethyllysine hydroxylase for the treatment of ischemic heart disease
  27. » Development of novel inhibitors for Mycobacterium tuberculosis isocitrate lyase
  28. » Biocidal and antifouling polymers for surfaces
  29. » Correlation between predicted and measured hydrogen bonding energies in model systems
  30. » The physicochemical parameters of veterinary drugs. A comparison study
  31. » The redox potentials of pro-drugs activated with bio-oxidation/reduction as calculated with DFT
  32. » New Chemical Technologies for the Depolymerisation of Lignin
  33. » Novel Synthetic Methods for Indole Construction
  34. » Sustainable Medicinal Chemistry with Biomass-Derived Building Blocks
  35. » Synthesis of Small Molecules that Influence PSA-NCAM: Potential Therapeutics for the Prevention of Glioblastoma Metastasis
  36. » Targeting Methicillin-Resistant Staphylococcus Aureus (MRSA) with bisindole natural products
  37. » Metallabenzenes as building blocks for new materials
  38. » Water purification by catalytic oxidation of pollutants
  39. » CO-Releasing Molecules with Targeted Pharmacological Activity
  40. » Antibody-Directed Cytotoxins (ADCs): Probing The Influence of Unnatural Amino Acid Components of Culicinin D
  41. » Asymmetric Synthesis of Benzannulated Spiroketals: Towards Novel Telomerase Inhibitors
  42. » Drug Discovery: Towards New Therapeutics for Mycobacterium tuberculosis (TB)
  43. » Molecular Basis of Cannabinoid CB1 Receptor Binding for Modulation of CNS Cell Signalling Pathways
  44. » Synthesis and Medicinal Chemistry of Natural Product Shellfish Toxins
  45. » Synthetic Studies towards Anticancer Opaliferin
  46. » Total Synthesis and Structural Elucidation of Callyspongiolide
  47. » The Impact of AGEs in Alzheimer’s Disease
  48. » Synthesis and Development of Antimicrobial Peptides containing the rare amino acid enduracididine in the Fight Against Bacterial Resistance
  49. » Synthesis of Amylin Mimics (Pramlitide) as a Treatment for Diabetes
  50. » Synthesis of New Generation Lipopeptide-based Antibiotics
  51. » Synthesis of the Novel Macrocyclic Peptide, Streptide
  52. » Characterisation of beverage antioxidants using cyclic voltammetry
  53. » Localised interaction of PEDOT electrodes with antioxidants using Scanning Electrochemical Microscopy (SECM)
  54. » A new multi-analyte sensor platform
  55. » The good without the bad: selective chelators for beryllium
  56. » Lighting up sugars – fluorescent probes for saccharides
  57. » Porphyrin compounds for dye sensitised solar cells and new functional materials
  58. » Cobalt complexes for catalytic hydrogen production
  59. » Flavour improvement of noni juice
  60. » Formation of Millard reaction products in sub-critical water extracted kiwifruit by-product fraction
  61. » Antifreeze Peptides for Preserving Texture in Frozen Foods
  62. » Lipopeptides with Broad Spectrum Antimicrobial and Antibiofilm Activities
  63. » Cell Penetrating Peptide Nanoparticles for Drug Delivery
  64. » Anti-Biofilm Peptides for Water Disinfection
  65. » New Enzymes for Water Treatment
  66. » The Chemical Transport and Characterisation of the Solid Solution of Cu2V2O7 and Co2V2O7
  67. » Preparation and physical characterisation of M2-xFexSnO4 mixed metal oxide phases

Exploiting marine natural products – antifouling polymer coatings


Project code:  SCI036

Quorum sensing is a mechanism of chemical communication used by bacteria to coordinate communities of cells. Such coordination can include the formation of biofilms, considered to the initial step in the process leading to biofouling of marine surfaces. Halogenated furanones natural products, such as rubrolides and fimbrolides are competitive inhibitors of quorum sensing, providing a template for the development of new antimicrobials and new antifouling agents. This project will lead to the synthesis and characterization of new analogues of these natural products: the functional groups to be included in the structures will include tethers that will allow them to be attached to polymers making them suitable for the preparation of antimicrobial films, paints and surfaces. The research you undertake in this summer project can be extended into a BSc Hons project, and eventually into a PhD if you're interested.

Supervisor

Brent Copp
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Marine chemical ecology


Project code:  SCI037

Marine chemical ecology is the science of investigating chemicals (natural products) produced by marine organisms and the roles they play in maintaining the evolutionary fitness of the organism. Such roles can include stopping biofouling (other things growing on top of the organism) or inhibiting predation. We've recently reported the first example of an alkyne containing amino alcohol lipid from a natural source – in this case, the sea squirt Pseudodistoma opacum which grows on rocks on West Auckland beaches. We're intrigued as to why the organism produces this compound, as well as several related alkyne containing structures, and seems to locate the compounds in its outer layers. In order to progress our studies, we plan to synthesise fluorescent compounds that will specifically tag the alkyne groups in these natural product. Once tagged, we'll be able to purify new analogues and we'll also be able to visualize where the compounds are specifically located in the organism. You'll need a background in chemistry to do this project – an interest in the marine environment and chemical ecology would also be useful but is not required. The research you undertake in this summer project can be extended into a BSc Hons project, and eventually into a PhD if you're interested.

Supervisor

Brent Copp
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New Zealand fungi as sources of new antibacterial lead compounds


Project code:  SCI038

Alexander Fleming’s discovery of penicillin, an antibiotic produced by the fungus Penicillium rubens, saw the dawn of a golden age for humankind. The routine use of antibiotics has since prevented a great deal of suffering and saved countless lives. Worryingly, that era is now coming to an end whereby antibiotic resistance means that many antibiotics are no longer effective as bacteria have developed the mean to evade and/or destroy these life-saving medicines. We are searching for new antibiotics using a large collection of fungi, most derived from plants and soil from New Zealand and the South Pacific. We are screening this collection to discover new compounds that kill the superbugs causing the greatest clinical threat to New Zealand: Staphylococcus aureus, Escherichia coli and Mycobacterium tuberculosis. This project will have you undertaking metabolomics profiling of antibacterial extracts, using HPLC and NMR to investigate the natural product components. Bioassay-guided fractionation will then be used to purify the active component(s) of each extract – testing of which against our bacteria panel will then reveal if we have something worth pursuing. The research you undertake in this summer project can be extended into a BSc Hons project, and eventually into a PhD if you're interested.

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Structure-activity relationship of new antimalarials


Project code:  SCI039

In our search for new cures for malaria, we have been exploring not only natural products isolated from marine organisms but also screening of compound libraries. Recent data has identified new chemical scaffolds that exhibit potent activity towards malaria in vitro. Three of these scaffolds that we're particularly interested are shown in the Figure below. It's early days for this project – we don't know the structure-activity relationship of these scaffolds at all – we just know that they're active. Come and join my group to work on investigating the potential of these compounds to act as inspiration for new cures for malaria. You'll synthesize and characterize novel analogues and then they'll be tested by collaborators against drug resistant strains of malaria. The research you undertake in this summer project can be extended into a BSc Hons project, and eventually into a PhD if you're interested.

Supervisor

Brent Copp
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Structure-activity relationship of new anti-tuberculosis agents


Project code:  SCI040

We've been interested in developing new therapeutics for the treatment of tuberculosis for a number of years now. Our initial studies focused on marine natural products as the inspiration for bioactive scaffolds – more recently these studies have relied upon new structural classes of compounds identified by mass screening campaigns undertaken by big pharma. Two examples of bioactive hits coming from the GSK screen are shown in the figure below. This project will center on the synthesis of new analogues of these hits – all compounds will be evaluated for activity against Mycobacterium tuberculosis both here in NZ and also in the US. Our US collaborators are particularly talented at determining the mechanism of action of anti-tuberculosis agents and so that is also one of the aims of this project. The research you undertake in this summer project can be extended into a BSc Hons project, and eventually into a PhD if you're interested.

Supervisor

Brent Copp
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Structure-activity relationship of polyamine-based antimalarials


Project code:  SCI041

Why not come and join us in the hunt for a new cure for malaria? The world desperately needs new drugs to treat malaria infection. For our part, we've been investigating NZ marine organisms for new compounds that inhibit the growth of malaria parasites. We've found orthidine F to be antimalarial with minimal toxicity – it's not a drug in itself, but does provide us with a valuable new idea on how to develop a drug. Since our initial finding, we've synthesized a lot of analogues, undertaking an extensive structure-activity relationship study. As a consequence, we now have several analogues that are close to cures for malaria in animal studies. In order to make these compounds into total cures, we're investigating new examples of polyamines that have multiple different antimalarial 'warheads' in their structures. This summer project is designed to get you into the lab and making novel analogues in this series – all compounds will be tested against malaria with our collaborators. The research you undertake in this summer project can be extended into a BSc Hons project, and eventually into a PhD if you're interested.

Supervisor

Brent Copp
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Sulfur compounds profiling in selected yeast strain fermentations


Project code:  SCI042

Fermentative sulfur compounds (FSCs) are pivotal species in defining, tuning and spoiling wine quality. Their contribution to the overall wine bouquet is controversial and it seems to have both negative and positive implications. As the name suggests these molecules are generated from the yeast metabolism, putatively from amino acids or amino acidic precursors. Nowadays, the most important sulfur compounds can be quantified at the School of Chemical Sciences; this information could be successfully combined with the yeast genetic knowledge generated at the School of Biological Sciences in order to further our understanding on the formation of these species.

The project will aim at profiling FSCs in the fermentation trials carried out with particular yeast strains for which the genetic analyses are currently undergoing. Gas chromatography coupled to mass spectrometry will be applied to detect and quantify these molecules.

Supervisor

Bruno Fedrizzi
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Bioanalytical Mode-of-Action Studies of Metal-based Anticancer Agents


Project code:  SCI043

Understanding the mode of action of anticancer agents at the molecular level is key to develop the next generation anticancer drugs. In this project, we will investigate the biomolecule interaction of metallodrugs using advanced bioanalytical methods to characterize binding kinetics and reaction products. These studies are important to select compounds for further preclinical development.

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Bioorganometallic Anticancer Chemotherapeutics: Preparation of Metal Complexes with Bioactive Ligands


Project code:  SCI044

The coordination of bioactive ligand systems to metal centres results in multimodal anticancer agents, i.e., anticancer drugs that have more than one of mode action. This design strategy is a promising route to overcome major limitations of current cancer chemotherapeutics. We will develop in this project new complexes between organometallic moieties and bioactive ligand systems and study their anticancer activity. 

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Design and Applications of Organometallic Complexes for Catalysis


Project code:  SCI045

The production of everyday products, such as pharmaceuticals, fertilisers and functional materials, is reliant on efficient chemical transformations to yield high amounts of the desired products at low cost. In this project, we will use different ruthenium complexes and study their catalytic activity in important chemical transformations with relevance to industry.

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Design of Multimodal Organometallic Anticancer Agents


Project code:  SCI046

In the past decade the design of targeted anticancer agents was among the most prolific research areas. However, more recently it has become apparent that the combination of more than one pharmacophore in a single molecule can result in anticancer agents with advantageous properties. In this project, we will work on the preparation of a new compound class to be tested on its tumour-inhibiting properties.

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Thermal stability analysis of bioactive compounds from Centella asiatica


Project code:  SCI047

Centella asiatica (gotu kola) is a herbal medicinal plant recognized for its health benefits such as revitalizing the nerves and brain cells, memory enhancing, wound healing and anti-inflammatory properties (Vasantharuba et al,2012). A PhD project is currently being carried out on “The Extraction, characterization and in vitro testing of bioactive compounds from Centella asiatica (gotukola) and development of a suitable food matrix/nutraceutical to deliver potential functional properties. Quantity and bioactivity of phytochemicals present in plant materials are affected by processing and storage conditions (Negi, 2012). Therefore, the thermal stability of bioactive compounds is important for their potential applications as food products or ingredients.

 

This project is to study the thermal behaviour of the isolated bioactive compounds using DSC and TGA.  The thermal degradation kinetics of reactions occurring in a given temperature range and glass transition temperature are important in interpreting thermal degradation of bioactive compounds (Brown, 1988; Ross, 2003). HPLC and FTIR will be used to quantify and to identify the changes in the known functional groups. The information obtained will help to establish a comprehensive understanding of the stability of the targeted bioactive compounds that will provide a base line in developing a suitable food matrix as a carrier.

References

Brown, Michael E. 1988. Introduction to Thermal Analysis: Techniques and Applications. New York, NY: Chapman and Hall.

Negi, P. S. (2012). Plant extracts for the control of bacterial growth: Efficacy, stability and safety issues for food application. International Journal of Food Microbiology, 156(1), 7-17.

Roos, Y. H. (2003). Thermal analysis, state transitions and food quality. Journal of Thermal Analysis and Calorimetry, 71(1), 197-203.

Vasantharuba Seevaratnam, Banumathi, P., Premalatha, M.R., Sundaram, S.P. and Arumugam, T. Functional properties of Centella asiatica (L.): A review. Int J Pharm Pharm Sci. 2012; 4: 8-14

Note:

Skills Required:  Preferably a third year Chemistry or Food Science student with a good analytical Chemistry background.

Available during summer from middle of November till end of February.

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Exploring the effect of fluorination on Claisen rearrangement reactions


Project code:  SCI048

The Acyl-Claisen rearrangement is a modern derivative of a classical organic chemistry reaction and allows multifunctional compounds to be prepared which we have found are extremely useful for the synthesis of complex biologically active compounds. In this project we will further explore the use of fluorinated materials in this reaction and discover conditions that allow a variety of substrates to be employed. This will then allow access to a range of poly-functional fluorinated compounds that are otherwise difficult to obtain. Fluorinated compounds are of considerable interest in drug-like molecules and in amino-acids/peptides for the interesting way they effect both the shape and electronic properties of the molecules. The student undertaking this project will be involved in organic synthesis, purification and compound characterisation (NMR, MS, IR, etc). They should have a reasonable knowledge of synthetic chemistry.

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Synthesis of biologically active lignan natural products


Project code:  SCI049

Lignans are a class of compound which has become the a target of particular interest to researchers, owing to their numerous biological activities including anti-cancer and cytotoxic properties and have also shown an array of pharmacological activities, including antifungal, antibacterial, antioxidant and anti-proliferative properties. In this project we will explore our recently developed methods to prepare a range of classes of lignan natural products using a common, easily made intermediate. This compound can be converted to both THF lignans and also aryl-tetralin lignans, both classes have highly bioactive members including clinically used drug. The student undertaking this project will be involved in organic synthesis, purification and compound characterisation (NMR, MS, IR, etc). They should have a reasonable knowledge of synthetic chemistry. 

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Understanding the biogenesis of H2S in yeast and its role cell signaling


Project code:  SCI050

There is growing recognition that H2S is a “gasotransmitter’’ that plays critical roles in cellular signalling and hormonal regulation. In humans, H2S has come under intense recent scrutiny because of its importance in cardiovascular diseases, cellular energetics and apoptosis. Since gaseous transmitters diffuse rapidly and with fine temporal control, understanding their modes and sites of synthesis is critical to understanding their biology. Several enzymes produce H2S, but their roles and relative importance in H2S signalling are not yet clear. In this project students will work on the synthesis of novel H2S donors. These molecules are synthetic complexes that break down under cellular conditions to product H2S and are required to study the effect of H2S in the inter-species signaling. The student undertaking this project will be involved in organic synthesis, purification and compound characterisation (NMR, MS, IR, etc) and also complex analytical techniques such as GCMS and LCMS and they should have a reasonable knowledge of synthetic and/or analytical chemistry.

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Synthesis of novel polymeric materials as surface active antimicrobial agents


Project code:  SCI051

Due to the increase in bacterial resistance there is a need to develop new antibacterial agents, in particular in a hospital and medical environment. In this project we will synthesize novel fluorescent antimicrobial polymers which not only kill bacteria upon contact but allow visualisation of the bacterial killing. The polymers will be designed so they can be used in a either a solution to be applied where desired or could be attached permanently to a surface to give an antibacterial surface. This project is conducted in collaboration with Prof Jadranka Travas-Sejdic. The student undertaking this project will be involved in organic synthesis, purification and compound characterisation (NMR, MS, IR, etc). They should have a reasonable knowledge of synthetic chemistry.

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Synthesis of novel polymeric materials for modern electronic materials


Project code:  SCI052

In this project the synthesis of novel polymeric materials will be undertaken with the prepared materials having the unique ability to not only conduct electricity but to also be adhesive and self-healing. The concept is that through appropriate design, materials can be made that are flexible, stretchy but also conducting and would allow for the generation of a new generation of conducting plastics for a wide range of applications, such as optoelectronics, bio-integrated electronic devices and conducting skin and soft robotics. This project is conducted in collaboration with Prof Jadranka Travas-Sejdic. The student undertaking this project will be involved in organic and polymer synthesis, purification and compound characterisation (NMR, Mass, IR, etc) as well as wide range of materials spectroscopy (AFM, SEM XPS etc). They should have an interest in synthetic and/or polymer chemistry.

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Synthesis of Novel inhibitors of Phospholipase C, an enzyme involved in cancer cell proliferation


Project code:  SCI053

Phospholipase C is a promising biological target for anticancer drug therapy with compounds binding to PLC showing marked growth inhibition of haematological tumour cells. We have recently discovered a class of compounds which are potent inhibitors of cell growth. Morphology and motility assays using triple negative breast cancer cell lines lead to the conclusion that PLC is the most probable bio-molecular target of these compounds however other important targets may be effected. The student working in this project will be involved in the design (computation modelling), synthesis and biological testing of novel compounds to treat cancer. Students with an interest in organic or medicinal chemistry are encouraged to apply.

Pre-requisites

Chem 230 (or equivalent to Stage II Organic Chemistry) and preferably Chem 330 (or equivalent to Stage III Organic Chemistry).

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Killing surface bacteria


Project code:  SCI054

Antimicrobial surfaces are extremely important to prevent contamination of materials used in everything from health care to food manufacturing. While a number of effective antimicrobial materials exist, attaching them to relevant surfaces so that they maintain their activity remains a challenge. This project will investigate methods of chemically attaching molecules to surfaces, and characterising the surfaces that are formed using ellipsometry, X-ray reflectometry, AFM and antimicrobial assays, towards optimising surface activity. Students will need to be comfortable with chemical laboratory skills.

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Making better biominerals


Project code:  SCI055

Nature is extremely effective at creating hybrid hard/soft materials, combining the strength of minerals with the flexibility and lightness of biological materials. This project will investigate attempts to create equivalent materials chemically, and characterising the result at the molecular and microscopic scale using ellipsometry, X-ray reflectometry, AFM and SEM, as we attempt to produce room temperature biomineralisation to rival sea shells! 

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Catalytic routes to robust polysilanes


Project code:  SCI056

Polysilanes, polymers containing an all silicon backbone, are very attractive for applications in electronics due to their semi-conducting ability. One of the current issues to access these polymers is that high molecular weight disubstituted polymer is not yet synthetically possible.  New catalysts will be assessed for selected substrates and the polymer will be analysed. Some inorganic synthesis including characterization in addition to mechanistic studies of the catalysis using NMR spectroscopy and GC-MS will be learned.

Supervisor

Erin Leitao
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Understanding the mechanism of the copper-catalysed oxidative cross-coupling of amines and phosphates to form phosphoramidates


Project code:  SCI057

Copper catalysed oxidative cross-coupling has been gaining much momentum in the past 5 years for the formation of main group-main group bonds (e.g. P-N, P-O, P-P, P-S, etc.).  Although the process is attractive in terms of its potential impact and widely-applied, very little is known about the mechanism of catalysis.  For example both Cu(I) and Cu(II) salts have been shown to be efficient catalysts for this transformation but presumably form the same active catalyst.  Mechanistic studies, model reactions and attempted synthesis of a new active copper catalyst will be pursued in order to gain clues as to how the catalysis works. The project will involve inorganic synthesis, characterization and mechanistic studies using NMR spectroscopy and GC-MS.

Supervisor

Erin Leitao
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Using catalysis to create new bioerodible materials useful in the construction of synthetic bone


Project code:  SCI058

Copper catalysed oxidative cross coupling will be used to make the first phosphoramidate polymers (containing a phosphorus-nitrogen backbone). Inorganic P-N polymers such as polyphosphazenes show promise as bioerodible materials but are formed using toxic reagents and harsh reaction conditions. Phosphoramidate compounds are tunable as well as accessible via catalytic routes. Expansion of the catalysis to synthesize polyphosphoramidates will be attempted along with corresponding characterization using NMR spectroscopy and MS.

Supervisor

Erin Leitao

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Behaviour of fingermarks on ice


Project code:  SCI059

We have reported that fingermarks can be deposited and recovered from ice and other difficult substrates, by staining with a dye that is soluble in fluorous solvents.  This project will investigate the conditions under which this is possible, and also investigate what is happening to the fingermark components over time.

Supervisor

Gordon Miskelly
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Hyperspectral imaging in chemical analysis


Project code:  SCI060

We have constructed a hyperspectral line imager suitable for imaging objects in the 1 mm – 10 cm size range. This project will apply this hyperspectral imager to systems in which spectral changes occur along one dimension.  This project will require calculations using the Matlab programming environment.

Supervisor

Gordon Miskelly
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Production and purification of recombinant bacterial and human trimethyllysine hydroxylase for the treatment of ischemic heart disease


Project code:  SCI061

Ischemic heart disease is one of the most common causes of mortality in the Western society. During periods of ischemia, the lack of blood flow to the heart limits the supply of oxygen, and causes the usually tightly regulated glucose and fatty acid oxidation pathways to be compromised. During ischemia, glycolysis (an oxygen independent metabolic pathway) serves as the main source of energy (ATP) production. However, the restoration of blood flow after an ischemic episode (reperfusion) does not restore the balance between glucose and fatty acid oxidations. Instead, fatty acid oxidation dominates as the major pathway for ATP production. Fatty acid oxidation has a much greater oxygen requirement than glucose oxidation, this, together with the disturbances in ionic and chemical homeostasis during ischemia and in the post-ischemic period, lead to an overall decrease in cardiac efficiency of between 25% and 40%.

 

Supervisor

Dr Ivanhoe Leung

It is possible to pharmacologically restore the balance between fatty acid oxidation and glucose oxidation (and hence the cardiac efficiency of the ischemic/reperfused heart), for instance, by limiting the mitochondrial fatty acid uptake. The transport of fatty acids from the cytoplasm to mitochondria requires a small carrier molecule called carnitine. By controlling the availability of carnitine (e.g. by limiting its biosynthesis), one can shift the cardiac energy source from fatty acid oxidation to glucose oxidation by restricting the amount of fatty acid substrates in the mitochondria and thereby forcing the cells to utilise glucose as the energy source instead.

Four enzymes are involved in carnitine biosynthesis. We are interested in characterising the first enzyme (trimethyllysine hydroxylase, TMLH) in this pathway, which catalyse the hydroxylation of trimethyllysine. This information will be useful for future developments of TMLH inhibitors for the treatments of ischemic heart disease. This summer scholarship will be the first step of this project, which will include cloning, production and purification of recombinant TMLH from both humans and bacteria.

 

There is no formal prerequisites to this summer scholarship, although an understanding of basic molecular biology and an enthusiasm in chemical biology will be helpful. Training and supervision in molecular biology and enzymology will be given throughout the summer period. Please contact me by email if you require any more information.

References

Jaswal, J. S. et al. Targeting fatty acid and carbohydrate oxidation – A novel therapeutic intervention in the ischemic and failing heart. Biochim. Biophys. Acta 20111813, 1333–1350.

Kazaks, A. et al. Expression and purification of active, stabilized trimethyllysine hydroxylase. Protein Express. Purif.2014104, 1–6.

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Development of novel inhibitors for Mycobacterium tuberculosis isocitrate lyase


Project code:  SCI062

Tuberculosis is an infectious disease that is caused by the airborne bacterium Mycobacterium tuberculosis. Once infected, Mycobacterium tuberculosis may exist in different metabolic states including a slow or non-growing ‘dormant’ state that is non-responsive to conventional anti-tuberculosis treatments. The failure to eliminate all populations of Mycobacterium tuberculosis from the patient may lead to the development of drug-resistant bacteria. It is estimated that about a third of the world's population has latent tuberculosis, the control of which is therefore crucial to the management and eradication of the disease.

 

Isocitrate lyase (ICL) is the first enzyme in the bacterial glyoxylate cycle, which is an important pathway for latentMycobacterium tuberculosis to synthesise carbohydrates and other biosynthetic products for survival. We are interested in the development of novel ICL inhibitors for the treatments of latent tuberculosis. This summer scholarship will form a key part of this project, which include the design and synthesis of ICL inhibitors, and in vitrocharacterisation of their inhibition potency against different isoforms of Mycobacterium tuberculosis ICL using biophysical techniques.

There is no formal prerequisites, although an interest and understanding of organic and medicinal chemistry and an enthusiasm in chemical biology will be helpful. Training and supervision will be given throughout the summer period. Please contact us by email if you require any more information.

References

Krátký, M. and Vinšová, J. Advances in mycobacterial isocitrate lyase targeting and inhibitors. Curr. Med. Chem.201219, 6126-6137.

Nandakumar, M. et al. Isocitrate lyase mediates broad antibiotic tolerance in Mycobacterium tuberculosis. Nat. Commun. 20145, 4306.

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Biocidal and antifouling polymers for surfaces


Project code:  SCI063

Antimicrobial and antifouling polymers have a potential to be used as permanent coating on surfaces. These can be synthesized by grafting of biocidial or antifouling polymers from pre-made functional polymer backbones. The biocidial/ antifouling polymers will be designed to firmly link to various surfaces, including metal, glass and plastic. The properties of the polymers, e.g. hydrophobicity, molecular weight, stability and biological activity will be characterised and controlled by the compositions of the polymers or block-copolymers. A student is sought, ideally with synthetic polymer chemistry skills, who would make such a proof-of concept polymer system, working alongside a post-doctoral fellow and a senior PhD student in the group of Prof. Travas-Sejdic. The project will be conducted in collaboration with Prof. Gillian Lewis from the School of Biological Sciences and supported by Biocide ToolBox programme.

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Correlation between predicted and measured hydrogen bonding energies in model systems


Project code:  SCI064

This project will establish the reliability of quantum mechanical methods in predicting biologically important hydrogen bonding interactions.

Supervisor

Jóhannes Reynisson

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The physicochemical parameters of veterinary drugs. A comparison study


Project code:  SCI065

The physiochemical properties of veterinary drugs will be investigated and compared to pharmaceuticals intended for humans.

Supervisor

Johannes Reynisson

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The redox potentials of pro-drugs activated with bio-oxidation/reduction as calculated with DFT


Project code:  SCI066

The redox properties of pro-drugs will be investigated using quantum mechanical methods.

Supervisor

Jóhannes Reynisson

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New Chemical Technologies for the Depolymerisation of Lignin


Project code:  SCI067

Biomass is the only renewable carbon feedstock that could potentially replace fossil fuels. The efficient conversion of biomass into fine chemicals is one of the great scientific challenges of the 21st century. This project will investigate new chemical technologies for the production of fine chemicals from lignin, an abundant biopolymer present in wood biomass.

Pre-requisites:

CHEM 330 or equivalent

Supervisor

Dr Jonathan Sperry

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Novel Synthetic Methods for Indole Construction


Project code:  SCI068

The indole ring system represents one of the most abundant and important heterocycles in nature, with over 6000 natural products possessing this ring system. Additionally, drugs containing the indole heterocycle below accounted for nearly US$8 billion in sales annually. In keeping with their importance, the development of new routes towards indoles is a central theme and ongoing challenge in contemporary organic synthesis. This project aims to develop a novel indole synthesis using some intriguing transition metal chemistry recently reported by our research group.

Pre-requisites:

CHEM 330 or equivalent

Supervisor

Dr Jonathan Sperry

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Sustainable Medicinal Chemistry with Biomass-Derived Building Blocks


Project code:  SCI069

The global chemistry community must reduce its reliance on fossil fuels and employ molecules derived from biorenewable sources in the production of society enhancing chemicals. This project will investigate the synthesis of modern, ‘sp3 rich’ medicinal chemistry candidates from building blocks derived from biomass (cellulose and chitin). The biological evaluation (anti-cancer, antibacterial, neuropsychiatric) will be performed through international collaborators.

Pre-requisites:

CHEM 330 or equivalent

Supervisor

Dr Jonathan Sperry

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Synthesis of Small Molecules that Influence PSA-NCAM: Potential Therapeutics for the Prevention of Glioblastoma Metastasis


Project code:  SCI070

Neural cell adhesion molecules (NCAM) are involved in neural plasticity, cell migration and cell-cell adhesion. When attached to a polysialic acid (PSA) motif, the resulting PSA-NCAM complex promotes cell migration and is thought to play a pivotal role in the metastasis of glioblastomas (brain tumours). In collaboration with the Centre for Brain Research at the University of Auckland, we have developed a library of small molecules that lower PSA-NCAM levels, but by an (as yet) unknown mechanism. This project will involve the chemical synthesis of further compounds that will help unravel the exact mechanism of action, an important step towards the goal of developing therapeutics that target the PSA-NCAM complex.

Pre-requisites:

Interest in medicinal chemistry, completed undergraduate synthetic chemistry paper(s).

Supervisor

Dr Jonathan Sperry

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Targeting Methicillin-Resistant Staphylococcus Aureus (MRSA) with bisindole natural products


Project code:  SCI071

Methicillin-resistant Staphylococcus aureus (MRSA), a bacterium that has evolved immunity to conventional antibiotics, is responsible for several difficult-to-treat infections in humans that often have a devastating outcome.1 MRSA infections are typically treated with the glycopeptides vancomycin and/or teicoplanin. Accordingly, there is an urgent need for new antibiotics in the clinic, in particular those that are not based on existing therapies. In collaboration with the University of British Columbia, we have recently shown that bisindole natural products selectively inhibit the pyruvate kinase (PK) of MRSA over human PK isoforms. This project will involve synthesising new bisindole natural products for MRSA PK inhibition studies, which will increase our understanding of how this inhibition occurs with this class of compounds.

Pre-requisites:

Interest in antibiotic development, completed undergraduate organic chemistry paper(s)

Supervisor

Dr Jonathan Sperry

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Metallabenzenes as building blocks for new materials


Project code:  SCI072

Metallabenzenes are compounds in which one of the CH groups of benzene has been formally replaced by a transition metal with its ancillary ligands.  We are interested in exploring the syntheses, reactivity and bonding of this intriguing new class of compounds.  The summer Scholarship project will involve the investigation of routes to functionalised metallabenzenes that will serve as precursors for the fabrication of new materials.

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Water purification by catalytic oxidation of pollutants


Project code:  SCI073

The use of the environmentally benign oxidant hydrogen peroxide for water purification is very attractive, but appropriate oxidation catalysts are required.  The Summer Scholarship project involves studies of newly discovered iron catalysts (Fe-TAMLs) that are incorporated into a new solid state technology we have developed for the oxidative destruction of dilute organic pollutants in water. Decontamination of the water occurs without contamination of the water with hydrogen peroxide, catalyst or base. 

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CO-Releasing Molecules with Targeted Pharmacological Activity


Project code:  SCI074

CO plays a key role as a gaseous messenger in the human body.  At very low concentrations CO has been shown to act as an intercellular messenger that elicits beneficial outcomes against inflammation, apoptosis and oxygen reperfusion damage.   There is a strong drive to develop water soluble transition metal (TM) compounds that can release CO inside the body selectively to target tissues.  This project involves the synthesis of special ligands that will give CORMs this important tissue selectivity.

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Antibody-Directed Cytotoxins (ADCs): Probing The Influence of Unnatural Amino Acid Components of Culicinin D


Project code:  SCI075

Antibody-directed cytotoxins (ADCs) are a promising class of drugs that aim to target specific cancerous tissues, by conjugation of a location-specific antibody to a highly toxic ‘warhead’ compound.

Culicinin D is the subject of a current ADC study underway in our research group, which involves both solid-phase peptide synthesis (SPSS) and asymmetric organic synthesis, based on our group’s expertise in both areas.

The three non-natural amino acids that occur in culicinin D (AHMOD, AMD and APAE) have be prepared enantioselectively at SCS and incorporated into the natural product polypeptide chain using SPSS in the Brimble peptide laboratory at SBS.  Following on from this platform, a series of chiral and heterocyclic AHMOD analogues will be synthesised, in order to identify culicinin D analogues with desirable activity/stablilty/solubility profiles for ADC development.

This project offers the opportunity to conduct high level asymmetric synthesis in the context of a medicinal drug discovery chemistry programme, based on a promising lead compound isolated from nature.

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Asymmetric Synthesis of Benzannulated Spiroketals: Towards Novel Telomerase Inhibitors


Project code:  SCI076

Telomerase inhibitors are of much current interest as a selective approach for the control of human cancer. The rubromycins are a unique class of antibiotics produced from a strain of Streptomyces that have been shown to inhibit human telomerase.

We have previously completed the synthesis of rubromycin, and are currently interested in novel catalytic methods for asymmetric synthesis of this unusual class of compound, that possess a single chiral centre at the spiroketal position.

We will investigate the asymmetric synthesis of benzannulated spiroketals using chiral Lewis acid catalysis, using a new route to prepare the necessary cyclisation substrates only recently identified in our group. In addition to probing the properties and stereochemistry of the compound class, we aim to develop new practical synthetic routes in order to assess the biological activity of chiral lead structures based on rubromycin.

This project offers the chance to work towards the development of new methods for chiral catalysis, based on the benzannulated spiroketal scaffold, as well as excellent general organic synthetic training.

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Drug Discovery: Towards New Therapeutics for Mycobacterium tuberculosis (TB)


Project code:  SCI077

Tuberculosis (TB) affects tens of millions globally is a significant economic and health burden, especially in developing countries. The menaquinone (vitamin K) biosynthetic pathway offers a new drug development target, as menaquinone is essential for the survival of Mycobacterium tuberculosis through its role as a redox shuttle in the mycobacterial electron transport chain.

In collaboration with A/Prof Shaun Lott, Dr Jodie Johnston (UoA, SBS) and Prof Greg Cook (Otago), we are currently investigating potential inhibitors of the enzyme MenD, that uses isochorismate as a substrate in the first committed step in menaquinone biosynthesis (above). The study draws together our group’s expertise in organic synthesis along with structural biology, enzymology and in silico computational methods for compound library screening and docking, in an effort to validate the menaquinone pathway as a target for new clinical TB treatments.

This project will provide an excellent introduction into the process of drug design in an academic context, with opportunities to work with specialists in related disciplines. The principal aim of the summer studentship will be to develop chemical methods to access novel inhibitor candidates, that will be characterised and evaluated for their activity against isolated MenD and whole cells.

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Molecular Basis of Cannabinoid CB1 Receptor Binding for Modulation of CNS Cell Signalling Pathways


Project code:  SCI078

Cannabinoid CB1 and dopamine D2 receptor signalling pathways are central to central nervous system (CNS) function and are implicated in neurobehavioural disorders. Evidence suggests that multi-receptor complexes involving the CB1 G-protein coupled receptor (GPCR), presently not well understood, play an important pharmacological role.

Current work in our group focuses on development of new ligands to target the CB1-D2 receptor complex, for investigation of cell signalling pathways and as lead compounds for new specific therapeutic agents for CNS disorders.

This research project will further explore the detailed nature of ligand binding to the CB1 receptor and resultant effects in downstream cell signalling pathways. The work will involve synthesis of a series of novel CB1 ligands, using chemistry that has been developed in our labs at SCS. These will then be investigated for receptor binding affinity, functional activity and signalling behaviour in the Glass lab in Pharmacology (FMHS).

The project would suit a student interested in the application of organic synthesis to the investigation of biological systems, ideally (but not necessarily) with some background in biological sciences or medicinal chemistry. Most of the time will be spent doing organic synthesis, but there will most likely be some opportunity to gain experience in pharmacology and the use of in silico molecular modelling.

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Synthesis and Medicinal Chemistry of Natural Product Shellfish Toxins


Project code:  SCI079

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The production of shellfish toxins during dinoflagellate algal blooms (‘red tides’) poses a significant health risk.  During these blooms the level of toxins within healthy shellfish can be harmful to humans, causing symptoms ranging from diarrhoea to extreme cardiovascular and neurotoxic effects, at exposures as low as a few parts per billion.

One of our research programmes is directed towards the synthesis and medicinal chemistry of complex shellfish toxins, with a specific focus on the newly-discovered spirocyclic imine, portimine. This compound was isolated in 2013 from algae collected in Northland.

Total and partial synthesis of the previously unknown structural motifs found in portimine will enable preparation of pharmacological probes for nicotinic acetylcholine receptors (nAChRs) and L-type calcium channels. nAChRs play an important role in signal transmission in the nervous system and are implicated in the progression of Alzheimer’s and Parkinson’s diseases. In addition, regulation of L-type calcium channels is used to treat cardiovascular disorders such as hypertension and angina pectoris.

Portimine also exhibits promising anti-cancer activity (selective cytoxicity against mammalian P388 leukemia cells, LC50 2.7 nM and apoptosis promotion via caspase 3 activation). The spiroimine macrocyclic structure of portimine poses an intriguing and demanding challenge to synthetic chemists, providing a unique opportunity to develop novel chemistry to enable efficient and stereoselective construction of the complex molecular architecture.

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Synthetic Studies towards Anticancer Opaliferin


Project code:  SCI080

Opaliferin was isolated from a culture of the pathenogenic fungus Cordyceps sp. NBRC 107954, which was collected from a cicada larva it had parasitised. The compound proved active against a number of cancer cell lines, and was isolated along with a number of biosynthetically related natural products from the cephalosporolide family, some of which have been the subject of previous study in our group.

The complex structure presents a number of challenges for asymmetric synthesis and also contains a spiroketal centre – a motif of particular interest to our research group.

Synthetic investigations will focus on access to the respective chiral building blocks required, and with these in hand, the assembly of the carbon skeleton. Work in the summer studentship will involve development of the key transformations to achieve these milestones, and progress permitting, advance to formation of the cis fused ring junction and the cyclic enol ether unit.

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Total Synthesis and Structural Elucidation of Callyspongiolide


Project code:  SCI081

Callyspongiolide is a 14-membered macrolide isolated in 2013 from an Indonesian marine sponge of the genus Callyspongia. Sponges of this genus are known to produce a diverse variety of bioactive secondary metabolites, including polyketides, polyacetylenes, alkaloids and cyclic peptides, but to date, callyspongiolide is the only reported macrolide.

 

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Callyspongiolide was found to exhibit potent cytotoxicity against a range of cell lines (L5178Y mouse lymphoma IC50320 nM, human Jurkat J16 T lymphocytes 70 nM, Ramos B lymphocytes 60 nM). Interestingly, addition of a caspase inhibitor (QVD-OPh) did not attenuate the activity of callyspongiolide, suggesting that it promotes cell death through a caspase independent mechanism.

The relative configuration of the C5, 7, 9 and 12 chiral centres was determined using a combination of 1D NMR proton coupling constants and transannular correlations in the 2D ROESY spectrum. Due to the extremely hindered nature of the secondary alcohol at C21, however, it did not prove possible to prepare any Mosher ester derivatives. As a result, the absolute stereochemistry of callyspongiolide, and the configuration at C21, has not been assigned to date.

The C14-19 yn-diene side chain linking the macrolide and bromoaryl domains is unprecedented in macrolide natural products reported to date, although known polyacetylenic algal metabolites are legion.

Total synthesis of the callyspongiolide will enable the complete structural elucidation of the natural product to be completed and permit convenient access to the key sub-structures for SAR investigation of the important biological activity observed.

This project will give an excellent introduction into the world of asymmetric synthesis, for those interested in the challenge of natural products and decoding their structure-activity relationships as pharmaceutical lead compounds.

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The Impact of AGEs in Alzheimer’s Disease


Project code:  SCI082

Alzheimer’s disease (AD) is a complex neurodegenerative disorder that results in progressive cognitive impairment, loss of memory and changes in behaviour. In 2011, 33.9 million people worldwide were diagnosed with AD, and it is estimated that this figure will triple by 2050 due to an increasing ageing population. Despite vast research spanning more than a century, current treatments for AD are still limited to modest symptomatic relief and the precise causes of AD remain largely unknown.

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Recently, new evidence has suggested that β-amyloid (Aβ) peptides (a hallmark of AD) that have been irreversibly modified by advanced glycation end products (AGEs) are more pathogenic than Aβ itself. However, the Aβ-AGE peptides used in these studies were prepared by the non-specific incubation of Aβ in glucose; this results in the formation of a complex mixture of Aβ-AGE peptides. Thus, the precise impact of individual AGEs on the biophysical properties of Aβ remains to be evaluated.

This project aims to prepare a small library of Aβ-AGE peptides, which will then undergo biological testing by Professor Michael Dragunow (FMHS). Successful candidates will employ organic synthesis techniques to prepare AGE building blocks followed by incorporation of the AGE building blocks into the Aβ peptide using solid phase peptide synthesis.

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Synthesis and Development of Antimicrobial Peptides containing the rare amino acid enduracididine in the Fight Against Bacterial Resistance


Project code:  SCI083

The emergence and spread of multi-drug-resistant bacteria is becoming a great threat to the health of humankind. The rate of bacteria developing resistance to both frontline and ‘last line of defence’ antibiotics is currently greater than the introduction of new compounds into clinical practice. This poses a severe problem as simple routine medical procedures will become life threatening as any resulting bacterial infection will not be easily and effectively treated.

 

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Naturally-occurring antimicrobial peptides (AMPs) are the tools by which many living organisms employ to defend themselves against bacterial attack. These unique compounds therefore show great potential as new source of antibiotics.

The ascidian metabolite 1 and mannopeptimycin 2 have been show to possess antimicrobial activity and contain the rare cyclic amino acid enduracididine (highlighted in blue).

This project will involve two aspects of modern synthetic chemistry. Firstly, an organic synthesis of enduracididine and secondly, solid phase peptide chemistry to incorporate End into synthetic polypeptides.  A successful synthesis of enduracididine will not only allow access to the above antimicrobial peptides and therefore the development of more potent analogues though SAR studies, but provide the basis for investigation of other peptides containing this intriguing amino acid e.g. teixobactin.

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Synthesis of Amylin Mimics (Pramlitide) as a Treatment for Diabetes


Project code:  SCI084

Diabetes Mellitus (DM) is a vast worldwide medical problem. The associated medical complications lead to heart disease, stroke, renal failure, premature blindness, amputation and significant mortality rates.  

 

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Existing therapies revolve around maintaining glucose at an appropriate level by administration of pramlitide (below), a 37 amino acid residue polypeptide a structurally related but non-toxic analogue of Amylin. However, pramlitide therapy suffers from several shortcomings such as low bio-availability and a half-life of just 48 mins thus necessitating a challenging 3 times daily injection. 

Lipidation of polypeptides or glycosylation of polypeptides is known to increase both circulatory half-life and bio-availability whilst maintaining biological effects.  Using click chemistry or thiol-ene chemistry, this research project aims to install lipids or sugars in a chemoselective manner on specific amino acid residues thereby synthesising modified pramlitide molecules that will be submitted to both biological evaluation (Prof. Debbie Hay, SBS) and estimation of half-life in the body by enzymatic hydrolysis. 

Successful candidates will employ organic synthesis techniques to access suitable glycosylated amino acids, solid phase peptide synthesis to prepare polypeptides and be exposed to biological testing techniques. 

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Synthesis of New Generation Lipopeptide-based Antibiotics


Project code:  SCI085

Antibiotic resistance has been recognised by the WHO as one of the greatest threats to humanity and infectious diseases rank as the second most common cause of death worldwide. This is further compounded by the observation that development of new structural classes of antibiotics has all but ceased in the past 40 years. 

 

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An emerging subset of peptide based antibiotics e.g. daptomycin are cyclic peptides containing a lipid or fatty acid.   They have been shown to be clinically relevant and are used as the “last line of defence” against otherwise untreatable bacterial infections.  The challenge remains, however, to efficiently produce new antibiotics based on a cyclic peptide scaffold incorporating the crucial lipid motif. 

Using our newly devised method of installing a lipid onto a peptide (a thiol-ene reaction), this projects aims to exploit and develop this chemistry to generate a chemical library of peptide based antibiotics, which will undergo biological testing against the most antibiotic resistant strains of bacteria. 

Successful candidates will be using organic synthesis techniques and modern methods of solid phase peptide synthesis.

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Synthesis of the Novel Macrocyclic Peptide, Streptide


Project code:  SCI086

Quorum sensing is a system of intercellular communication by which some species of pathogenic bacteria coordinate the regulation of gene expression and production of virulence factors in order to have maximum impact on their environment. As a result, quorum sensing has significant implications in the pathogenicity of disease-causing bacteria. Understanding the transcription products involved in quorum sensing systems provides insight into the regulation of these systems and may help identify potential biological targets for the development of novel antibiotic compounds that inhibit quorum sensing. 

 

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Streptococcal bacteria use peptide signals as a means of intraspecies communication. These peptides can contain unusual post-translational modifications, providing opportunities for expanding our understanding of nature’s chemical and biosynthetic repertoires. Streptide is a novel macrocyclic peptide produced by Streptococcus thermophilus, a non-pathogenic streptococcal model strain that is used in the fermentation of dairy products. Although it does not express the virulence factors of its pathogenic relatives (which include Streptococcus mitis, Streptococcus pyogenes and Streptococcus pneumoniae), it does harbour a new, recently identified quorum sensing system common to many streptococci, including pathogenic strains.

Streptide contains an unprecedented tryptophan-lysine cross-link (C-7 to β) in the macrocycle.  In combination with solid phase peptide synthesis, C-H activation will be used to install the tryptophan-lysine cross-link and synthesise the unnatural amino acid (blue) required to complete an initial total synthesis of streptide.

A successful synthesis will allow evaluation of the biological activity of streptide and will provide the basis for future syntheses of related cross-link-containing macrocyclic peptides.

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Characterisation of beverage antioxidants using cyclic voltammetry


Project code:  SCI087

In this project, the electrochemical procedure of cyclic voltammetry will be applied to the antioxidants present in a series of alcoholic beverages, including beer and fortified drinks. Comparisons will be made with standard Food Science antioxidant assays, and a wide range of beverages of different strengths will be surveyed.

Supervisor

Prof Paul Kilmartin

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Localised interaction of PEDOT electrodes with antioxidants using Scanning Electrochemical Microscopy (SECM)


Project code:  SCI088

In this project the technique of scanning electrochemical microscopy (SECM) will be applied to different types of PEDOT electrodes prepared on gold substrates, and the interaction between PEDOT and beverage antioxidants will be examined in situ.  If available, in situ electrochemical AFM will be applied as a further means to profile the electrode surface properties.

Supervisor

Prof Paul Kilmartin

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A new multi-analyte sensor platform


Project code:  SCI089

Traditional chemical sensors are designed for one analyte (or target) at a time.  We are using a newly devised gold-tipped silicon array to develop a platform for multi-analyte sensors for use, for example, in the dairy industry.  The project will involve using surface attachment chemistry to attach sensors to the gold tips and measuring the response to various analytes.

Activities:

chemical synthesis, surface chemistry, spectroscopy, electrochemistry

Skills:

Stage 2 or 3 chemistry

Supervisor

Prof Penny Brothers

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The good without the bad: selective chelators for beryllium


Project code:  SCI090

The element beryllium is increasingly utilised in consumer, scientific and commercial applications from mobile phones and speaker drivers, to golf clubs and the James Webb Space Telescope. The chemistry of this element has largely been overlooked due to its high toxicity.    The non-toxic elements boron and aluminium will be used to model the chemistry of beryllium. We will develop selective agents for binding beryllium with the aim of finding new directions in detection, therapeutic and remediation technologies for beryllium.

Activities:

Chemical synthesis

Skills:

Stage 2 or 3 organic or inorganic chemistry

Supervisor

Prof Penny Brothers

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Lighting up sugars – fluorescent probes for saccharides


Project code:  SCI091

We have developed a method of attaching a fluorescent label directly to glucose. This allows for highly targeted, sensitive, fluorescent labelling of sugars which could be applied to the detection of specific sugar disease markers on cell surfaces, the labelling of saccharide capsules coating pathogenic bacteria, and the determination of polysaccharide fine structure in biology and materials science.  The project will involve exploring the chemistry of the fluorescent BODIPY molecule and its chemistry with sugars.

Activities:

Chemical synthesis and spectroscopy

Skills:

Stage 2 or 3 organic or inorganic chemistry

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Porphyrin compounds for dye sensitised solar cells and new functional materials


Project code:  SCI092

Porphyrins are the pigment which gives heme its red colour.  These planar, electron-rich molecules are good absorbers of light and can also bond to small gas molecules.  They are investigated widely as dyes for solar cells, as the active site in gas sensors, and for their ability to act as building blocks in new functional materials.  This project will explore the synthesis of a range of porphyrins designed for these applications.

Activities:

Chemical synthesis, surface chemistry, spectroscopy, electrochemistry

Skills:

Stage 2 or 3 chemistry

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Cobalt complexes for catalytic hydrogen production


Project code:  SCI093

The efficient production of hydrogen from sustainable sources is an important goal in the search for new fuels.  We have recently developed a cobalt-BODIPY dye complex which can be used for the photocatalytic production of hydrogen from water.  This kind of technology is directed towards the use of sunlight to drive hydrogen production.

Activities:

Chemical synthesis, laser spectroscopy, electrochemistry

Skills:

Stage 2 or 3 chemistry

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Flavour improvement of noni juice


Project code:  SCI094

This project involves product formulation and sensory evaluation of noni juice.

Successful candidate must has good experience in food product development and sensory evaluation, has basic chemical analysis skills and is keen about the topic.

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Formation of Millard reaction products in sub-critical water extracted kiwifruit by-product fraction


Project code:  SCI095

To study the formation of Millard reaction products (MRPs) from kiwifruit by-products during sub-critical water extraction process.

The successful candidate must have good interest to work in the lab environment, has basic analytical chemistry skill, be committed and can follow lab regulation strictly. 

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Antifreeze Peptides for Preserving Texture in Frozen Foods


Project code:  SCI096

Antifreeze proteins (AFPs) enable organisms like polar fish to survive the freezing temperatures of their natural habitat. As well as being cryoprotective, AFPs have the ability to influence the size, morphology and aggregation of ice crystals which can be used in food technology, where the growth of ice crystals in frozen foods is of primary concern. AFPs expressed in yeast have been used in the ice-cream industry for creating a smooth texture and preserving ice crystal size distribution until consumption. However, infusing large protein molecules into fruits and vegetables is not a viable option and there are no analogous commercial products in the frozen fruit and berry industries. In this project we aim to develop tailor-made analogues of natural AFPs for fundamental mechanistic studies as well as potential applications in the frozen food industry. Ice crystal morphology studies and texture analysis of frozen fruits using the synthetic peptides will be done in collaboration with the Food Science group at UoA. This interdisciplinary project applies cutting edge peptide research to the needs of the frozen fruit industry which plays a major role in New Zealand’s economy. The summer student working in this project will be trained in Solid Phase Peptide Synthesis, HPLC purification and food science techniques relevant to the project.

Supervisor

Viji Sarojini

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Lipopeptides with Broad Spectrum Antimicrobial and Antibiofilm Activities


Project code:  SCI097

According to the World Health Organisation, the rapid emergence of multidrug resistant ‘superbug’ bacteria has created an urgent need to develop novel classes of antimicrobial agents. Unfortunately, over the last 30 years, no major types of antibiotics have been developed. Cationic antimicrobial peptides (CAPs) are promising therapeutics to address the challenge of bacterial resistance. The near success of MSI-78 (pexiganan acetate) and MX-226 or CPI-226 (Omiganan) in reaching the clinic, provide us with the enthusiasm to overcome the current roadblocks of CAPs (e.g. proteoclytic susceptibility) to achieve clinical implementation of AMPs. To this end, we have developed several linear and cyclic lipopeptides with nonprotein amino acids which have shown low micromolar activity against bacterial pathogens and the ability to lyse bacterial membranes. This project will develop stereoisomers of our potent lipopeptides through chemical synthesis and investigate their potency and mechanism of action. The summer student working in this project will be trained in Synthetic Organic Chemistry, Solid Phase Peptide Synthesis, HPLC purification and spectroscopic techniques such as NMR and Circular Dichroism. 

Supervisor

Viji Sarojini

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Cell Penetrating Peptide Nanoparticles for Drug Delivery


Project code:  SCI098

Increase in the number of new therapeutics that fails to reach the clinic due to poor delivery has made novel drug delivery systems an important consideration in therapeutic development. Cell penetrating peptides (CPP) are promising tools for delivering biologically active molecules like oligonucleotides and proteins into cells. The carrier-biomolecule (cargo) interactions are dictated by the sequence of the CPP. Mechanism of cellular drug internalization by CPPs is not well understood. This project aims to develop short synthetic peptides derived from the trans-activating regulatory protein (TAT) of the human immunodeficiency virus (HIV) which is the first known CPP ever. The TAT sequence will be synthesized by Solid Phase Peptide synthesis and conjugated to short oligonucleotide chains. It is expected that the peptide-oligonucleotide complex will form stable nanoparticles facilitating the entry of the drug into the cell through the plasma membrane. Morphological features of the CPP-oligonucleotide complex will be investigated by scanning electron microscopy (SEM) and light scattering measurements in collaboration with Prof Jadranka Travas-Sejdic. This project also involves collaboration with the Auckland Cancer Society Research Centre.

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Anti-Biofilm Peptides for Water Disinfection


Project code:  SCI099

Billions of people lack access to safe drinking water and millions die annually from diseases transmitted through the consumption of unsafe water. Waterborne infectious agents causing such diseases include bacteria, fungi, protozoa and viruses. Viruses are of particular concern and account for half of the emerging pathogens in recent times. The main water disinfectant used worldwide, free chlorine, is ineffective in controlling certain waterborne pathogens, particularly Mycobacterium avium, ubiquitous in biofilms found in water distribution systems. Growing of biofilms within ageing water distribution systems is a significant challenge facing infrastructure providers across the world. Using our previous experience in developing antimicrobial peptides for biofilm control, this project aims to develop antimicrobial peptides with potency and selectivity towards Mycobacterium avium biofilms found in water distribution systems. The summer student working in this project will be trained in Solid Phase Peptide Synthesis, HPLC purification and microbiology techniques relevant to the project.

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New Enzymes for Water Treatment


Project code:  SCI100

In developing as well as in industrialized nations, a growing number of contaminants are entering the aqueous environment from human activity. Organic herbicides/pesticides for controlling weeds, insects and fungi in agriculture comprise the largest group of xenobiotic compounds deliberately introduced into the environment. These compounds, and their metabolites end up in drinking water at concentrations exceeding the 0.1µg/L threshold of pesticide residues in drinking water. This translates into an immediate need for effective, low-cost, robust water treatment methods to remediate waters without further stressing the environment or endangering human health. This project aims to undertake the basic research to develop biodegradable peptide-based scavenger enzymes for water remediation applications. The summer student working in this project will be trained in Molecular Modelling, Solid Phase Peptide Synthesis, HPLC purification and residue scavenging techniques relevant to the project.

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The Chemical Transport and Characterisation of the Solid Solution of Cu2V2O7 and Co2V2O7


Project code:  SCI240

Supervisor

A/P Tilo Soehnel

This project is in the field of solid-state materials and deals with the preparation and characterisation of vanadium-compounds with mixed transition metal content. The goal is to prepare solid solutions of Cu2V2O7 and Co2V2O7 to study the influence of doping on electric and magnetic properties on single crystals.

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Preparation and physical characterisation of M2-xFexSnO4 mixed metal oxide phases


Project code:  SCI241

Supervisor

A/P Tilo Soehnel

This project focuses on synthesis and physical characterization of novel inorganic materials based on Fe-based spinel oxides M2-xFexSnO4, which have not been systematically studied yet. The structural changes and the to the changes in properties will be studied upon doping with transition metals. By use of a wide range of spectroscopic and other analytical methods, we are hoping to go beyond a mere description of coordination and structure of the products.

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