Chemical Sciences

  1. » Restoring the activity of old antibiotics
  2. » New Zealand fungi as sources of new antibiotics
  3. » Synthesis of New Generation Lipopeptide-based Antibiotics
  4. » Synthesis of the Novel Macrocyclic Peptide, Streptide
  5. » Development of Antimicrobial Peptides in the Fight Against Bacterial Resistance
  6. » Synthesis of Amylin Mimics as a Treatment for Diabetes
  7. » The Impact of AGEs in Alzheimer’s Disease
  8. » Chemical Synthesis of Prostate Cancer Cell Growth Inhibitors Leucinostatins
  9. » Chemical Synthesis Of a Conotoxin Derived from the Venom of Cone Snails
  10. » Synthesis of Pseudoxylallemycins, Antimicrobial Cyclic Tetrapeptides
  11. » TLR2 Activation: Modulating the Activity of Lipopeptide Constructs
  12. » Total Synthesis and Medicinal Chemistry: Spirocyclic Imine Natural Products
  13. » New Chemical Reactions: Synthetic Applications of Vinyl Azide and Vinyl Amides
  14. » Drug Discovery: New Antibiotics Based on Novel Aminoacid Components
  15. » Natural Product Synthesis: Asymmetric Synthesis of Spiroketals
  16. » Bioorganometallic Anticancer Chemotherapeutics: Preparation of Metal Complexes with Bioactive Ligands
  17. » Design of Multimodal Organometallic Anticancer Agents
  18. » Design and Applications of Organometallic Complexes for Catalysis
  19. » Bioanalytical Mode-of-Action Studies of Metal-based Anticancer Agents
  20. » Synthesis of biologically active lignan natural products
  21. » Synthesis of Novel inhibitors of Phospholipase C, an enzyme involved in cancer cell proliferation
  22. » Exploring the effect of fluorination on Claisen rearrangement reactions
  23. » Understanding the biogenesis of H2S in yeast and its role cell signaling
  24. » Synthesis of novel polymeric materials as surface active antimicrobial agents
  25. » Synthesis of novel polymeric materials for modern electronic materials
  26. » Using catalysis to create new bioerodible materials useful in the construction of synthetic bone
  27. » Understanding the mechanism of copper-catalysed cross-coupling with main-group substrates
  28. » Catalytic routes to robust polysilanes
  29. » Surfaces for Dynamic Microfluidics
  30. » Behaviour of fingermarks on ice
  31. » Hyperspectral imaging in chemical and forensic analysis
  32. » Development of novel inhibitors for Mycobacterium tuberculosis isocitrate lyase
  33. » Recombinant protein expression and purification
  34. » Mechanistic and mutagenesis studies of grape (Vitis vinifera) polyphenol oxidase
  35. » Atomic force microscopy on polymers
  36. » Electrospinning conducting elastomers
  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. » Correlation between predicted and measured hydrogen bonding energies in model systems
  41. » The redox potentials of pro-drugs activated with bio-oxidation/reduction as calculated with DFT
  42. » The physicochemical parameters of veterinary drugs. A comparison study
  43. » New Chemical Technologies for the Depolymerisation of Lignin
  44. » Sustainable Medicinal Chemistry with Biomass-Derived Building Blocks
  45. » Novel Synthetic Methods for Indole Construction
  46. » Synthesis of Small Molecules that Influence PSA-NCAM: Potential Therapeutics for the Prevention of Glioblastoma Metastasis
  47. » Zwitterionic Materials for Enhanced Molecular Self-Assembly in Organic Solar Cells
  48. » Characterisation of beverage antioxidants using cyclic voltammetry
  49. » Localised interaction of PEDOT electrodes with antioxidants using Scanning Electrochemical Microscopy (SECM)
  50. » Lighting up sugars – fluorescent probes for mono-saccharides
  51. » Lighting up sugars – fluorescent probes for poly-saccharides
  52. » Porphyrin compounds for dye sensitised solar cells
  53. » Porphyrin compounds for new functional materials
  54. » Cobalt complexes for catalytic hydrogen production
  55. » The stability of microencapsulated cranberry powder
  56. » New Enzymes for Water Treatment
  57. » Anti-Biofilm Peptides for Water Disinfection
  58. » Antifreeze Peptides for Preserving Texture in Frozen Foods
  59. » Lipopeptides with Broad Spectrum Antimicrobial and Antibiofilm Activities
  60. » Cell Penetrating Peptide Nanoparticles for Drug Delivery
  61. » Antimicrobial Peptides against Food Spoiling Psychrophiles
  62. » De novo Designed Models of Protein ß-sheets

Restoring the activity of old antibiotics


Supervisor

Assoc Prof Brent Copp

Dr Siouxsie Wiles

Discipline

Chemical Sciences

Project code: SCI029

Antibiotic drug resistance is a rapidly growing problem for global public health. In many cases, current antibiotics simply don't work anymore. We've discovered a new class of molecule that can restore the antibiotic action of drugs against a human pathogenic Gram negative microbe, Pseudomonas aeruginosa. Since our initial finding, we've synthesized a lot of analogues, undertaking an extensive structure-activity relationship study, to the point that we now have developed some exceptionally potent analogues. We still don't know exactly why our compounds work though. This summer project is designed to get you into the lab and making novel analogues in this series that can help us understand how these compounds work. 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.

New Zealand fungi as sources of new antibiotics


Supervisor

Assoc Prof Brent Copp

Dr Siouxsie Wiles

Discipline

Chemical Sciences

Project code: SCI030

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.

New Zealand fungi as sources of new antibiotics

Synthesis of New Generation Lipopeptide-based Antibiotics


Supervisor

Distinguished Professor Margaret Brimble

Dr Paul Harris

Discipline

Chemical Sciences

Project code: SCI031

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.

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.

http://brimble.chem.auckland.ac.nz/?q=research

Synthesis of the Novel Macrocyclic Peptide, Streptide


Supervisor

Distinguished Professor Margaret Brimble

Dr Dan Furkert

Dr Paul Harris

Discipline

Chemical Sciences

Project code: SCI032

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.

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 beta) 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.

http://brimble.chem.auckland.ac.nz/?q=research

Development of Antimicrobial Peptides in the Fight Against Bacterial Resistance


Supervisor

Distinguished Professor Margaret Brimble

Dr Paul Harris

Discipline

Chemical Sciences

Project code: SCI033

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.

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 and mannopeptimycin 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.

http://brimble.chem.auckland.ac.nz/?q=research

Development of antimicrobial peptides in the fight against bacterial resistance

Synthesis of Amylin Mimics as a Treatment for Diabetes


Supervisor

Distinguished Professor Margaret Brimble

Dr Paul Harris

Discipline

Chemical Sciences

Project code: SCI034

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. 

Existing therapies revolve around maintaining glucose at an appropriate level by administration of pramlitide, 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.

http://brimble.chem.auckland.ac.nz/?q=research

The Impact of AGEs in Alzheimer’s Disease


Supervisor

Distinguished Professor Margaret Brimble

Dr Harveen Kaur

Discipline

Chemical Sciences

Project code: SCI035

Alzheimer’s disease (AD) is a complex neurodegenerative disorder that results in progressive cognitive impairment, loss of memory and changes in behaviour. In 2011, 34 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.

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

This project aims to prepare a small library of Aβ-AGE peptides, which will then undergo biological testing by Associate Professor Nigel Birch (SBS) and 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 A-beta peptide using solid phase peptide synthesis.

http://brimble.chem.auckland.ac.nz/?q=research

Chemical Synthesis of Prostate Cancer Cell Growth Inhibitors Leucinostatins


Supervisor

Distinguished Professor Margaret Brimble

Dr Iman Kavianinia

Discipline

Chemical Sciences

Project code: SCI036

Leucinostatins are naturally occurring peptides which were isolated from Penicillium lilacinum almost 40 years ago. Twenty-four different structures have been described in the leucinostatin family, with leucinostatins A and B significantly suppressing prostate cancer growth in a coculture system in which prostate stromal cells stimulated the growth of DU-145 human prostate cancer cells through insulin-like growth factor-I.

In order to execute the total synthesis of leucinostatins A and B, synthesis of the seven unnatural amino acid building blocks namely: (2S)-N,N-dimethylpropane-1,2-diamine (DMPD), (S)-N-methylpropane-1,2-diamine (MPD), beta-hydroxyleucine (beta-HyLeu), 4-methyl-L-proline (MePro), (4S,2E)-4-methylhex-2-enoic acid (MeHA), (2S,4S,6S)-AHMOD  and (2S,4S,6R)-AHMOD is required. Site-specific individual incorporation of a (2S,4S,6S)-AHMOD  or (2S,4S,6R)-AHMOD  residue into the peptide framework of leucinostatin is also required to determine the absolute configuration at C-6 in the AHMOD residue.

Solid-phase peptide synthesis (SPPS) techniques will be used for peptide elongation to avoid tedious purification of the intermediates, thus expediting the assembly of the target nonapeptide.

This research project aims to establish a comprehensive structure–activity relationship of leucinostatins A and B in order to search for analogues with improved anti-tumor properties.

http://brimble.chem.auckland.ac.nz/?q=research

Chemical synthesis of prostate cancer cell growth inhibitors leucinostatins

Chemical Synthesis Of a Conotoxin Derived from the Venom of Cone Snails


Supervisor

Distinguished Professor Margaret Brimble

Dr Paul Harris

Discipline

Chemical Sciences

Project code: SCI037

Cone snails have evolved a venomous harpoon able to paralyse prey with an arsenal of toxic compounds, such as conotoxins, which show great promise in the treatment of conditions such as pain and neuromuscular disorders. κA-conotoxins are a major component of the venom of several species of fish-hunting cone snail, but as a class of compounds have been less well studied due to their molecular complexity and post-translational modifications.

CcTx is a 30 residue glycopeptide that contains an intricate serine-linked pentasaccaride, 3 intramolecular disulphide bonds, several hydroxylated proline residues and a C-terminal alpha helix spanning residues 23Ser-27Thr.  The unique pentasaccaride moiety, which contains several rare and unnatural L-sugars, probably plays a key role in its bioactivity.

Using chemical synthesis techniques this project will embark on a total synthesis of CcTx using glycosylation and peptide chemistry to assemble from individual amino acids, the fully functional molecule. Candidates will become well versed in the modern methods of glycopeptide chemistry including exposure to advanced biophysical techniques such as HPLC and mass spectrometry.

http://brimble.chem.auckland.ac.nz/?q=research

Chemical synthesis of a conotoxin derived from the venow of cone snails

Synthesis of Pseudoxylallemycins, Antimicrobial Cyclic Tetrapeptides


Supervisor

Distinguished Professor Margaret Brimble

Dr Harveen Kaur

Dr Dan Furkert

Discipline

Chemical Sciences

Project code: SCI038

Multidrug antibiotic resistance poses an increasingly urgent threat to human health. Amongst antibiotic resistant species, Gram-negative bacteria in particular have become resistant to almost all available treatments. Whilst a number of antibiotics are currently being developed to target Gram-positive infections, only few are in progress for Gram-negative infections.

Recently, a family of four cyclic tetrapeptides, namely pseudoxylallemycins A-D, isolated from the termite-associated fungus Pseudoxylaria sp. X802 were found to exhibit Gram-negative antimicrobial activity (MICs of 12.5-25.0 μg/mL), cytotoxicity (HeLa cells, CC50 10.3-49.5 μg/mL) and antiproliferative activity (HUVEC cells, GI50 4.3-33.8 μg/mL; K-562 cells, GI50 4.2-42.8 μg/mL).

Pseudoxylallemycins B-D contain unique allene moieties (highlighted in blue), which rarely occur in natural products. Using a combination of organic and peptide chemistry, this project aims to synthesise the natural products pseudoxylallemycins A-D and structurally related analogues, which will then be evaluated for antimicrobial activity in collaboration with Professor Greg Cook (Uni of Otago).

http://brimble.chem.auckland.ac.nz/?q=research

TLR2 Activation: Modulating the Activity of Lipopeptide Constructs


Supervisor

Professor Margaret Brimble

Dr Geoff Williams

Professor Rod Dunbar

Discipline

Chemical Sciences

Project code: SCI039

Toll-like receptor 2 (TLR2) is a highly conserved membrane pattern recognition receptor that has evolved to recognize Lipoprotein motifs expressed by foreign pathogens. On binding of an agonist motif the receptor is activated and, after internalisation of the foreign agent, then modulates the production of signalling factors that up-regulate an effective immune response to that pathogen.

It has been shown that activation of TLR2 can be attained with S-(2,3-bispalmitoyloxypropyl)Cysteine-based (Pam2-Cys and Pam-1-Cys) lipid motifs present in the cell wall of Gram-positive bacteria. Thus, by creating a construct in which this lipid is linked to a suitable peptide epitope, the TLR2 receptor can be recruited into producing a highly targeted immune response that can then be directed against cancerous cells within a host.

The linker portion of the lipid-peptide construct epitope has conventionally been Ser-Lys-Lys-Lys-Lys but it is still not clear to what extent TLR2 activation is governed by this sequence. The project aims to investigate this question by exchanging the key Serine residue by other amino acids – both natural and unnatural – to gauge the effect on receptor activation and through this to better modulate the immunogenic response.

The relative activity of the library of analogues thus generated will be evaluated in the HEK-blue™ cell assay.

The skills necessary to carry this project out will include some organic synthesis and modern solid-phase peptide synthesis and purification.

http://brimble.chem.auckland.ac.nz/?q=research

Total Synthesis and Medicinal Chemistry: Spirocyclic Imine Natural Products


Supervisor

Distinguished Professor Margaret Brimble

Dr Dan Furkert

Discipline

Chemical Sciences

Project code: SCI040

Shellfish toxins produced by dinoflagellates in during algal blooms such as portimine and gymnodimine are a significant risk to human health – but also provide a stern challenge for existing synthetic methods, and inspirational leads for medicinal chemistry and drug development.  Portimine  exhibits promising selective anti-cancer activity and apoptosis induction, and gymnodimine is an extremely selective ligand for the nicotinic acetylcholine receptors important in nerve signal transduction. Our group has a strong ongoing interest in the total synthesis of these complex and highly bioactive molecules, and revealing their potential use in medicinal chemistry through structure-activity studies.

Working in this area will give new students a superb opportunity to be involved in the exciting challenge of natural product synthesis, and gain an insight into the tactics and techniques of complex organic chemistry. Projects currently available in this specific area include; stereoselective assembly of key spirocyclic imine natural product fragments, development of new methods to prepare challenging chemical structures, and determination of structure-activity relationships in partnership with our biochemistry collaborators.

http://brimble.chem.auckland.ac.nz/?q=research

New Chemical Reactions: Synthetic Applications of Vinyl Azide and Vinyl Amides


Supervisor

Distinguished Professor Margaret Brimble

Dr Dan Furkert

Discipline

Chemical Sciences

Project code: SCI041

The discovery and development of new reactions offers opportunities to improve synthetic routes to important materials, readily and selectively access previously challenging structures and improve our fundamental understanding of chemical processes. Recently, our group uncovered an unexpected reaction to form alpha,beta-unsaturated vinyl amides directly from esters. Our investigations revealed that the reaction likely involves an unusual [3+2] cylcloaddition of an ester or aldehyde enolate, with in situ generated vinyl azide, a little-used reagent with an intriguing history dating back to original work in 1910.

We are keenly pursuing the possibilities opened up by this new reactivity; for rapid access to previously hard-to-access vinyl amides (versatile synthetic intermediates and useful industrial polymer feedstocks) and synthesis based on them; to explore the mechanistic basis of their reactivity through experiment and calculation (e.g. transition state TS1); and finally to assess the potential of vinyl azide itself in organic synthesis. This project offers an unusual and fast-moving chance to discover new areas of chemistry, while expanding your synthesis and lateral thinking skills.

http://brimble.chem.auckland.ac.nz/?q=research

New chemical reactions - synthetic applications of vinyl azide and vinyl amides

Drug Discovery: New Antibiotics Based on Novel Aminoacid Components


Supervisor

Distinguished Professor Margaret Brimble

Dr Dan Furkert

Discipline

Chemical Sciences

Project code: SCI042

Growing incidence of antimicrobial resistance to clinically used antibiotic drugs is an immediate global health concern, as recently highlighted by the World Health Organisation (WHO), US and NZ governments. Due to the low numbers of new pharma drug candidates currently entering the development pipeline, academia and small biotech firms have an important role to play in generating novel compounds to address the resistance problem. Teixobactin, a complex antimicrobial peptide recently isolated from a culture of soil bacteria, demonstrates not only extremely potent activity against clinically-relevant resistant strains of MRSA, vancomycin-resistant Enterococci (VRE), M. tuberculosis (Mtb) and C. difficile, but crucially a very low incidence of acquired resistance.

The rare aminoacid enduracididine (End) is critical to the activity of teixobactin, but has proven surprisingly challenging to synthesise. Work on this project offers the chance to learn important synthesis skills in a drug discovery context, on a problem of genuine global relevance. The development of a robust and efficient route to End itself and the preparation of new active analogues to support medicinal chemistry studies will be the initial project goals, with the eventual aim of identification and synthesis of new antimicrobial peptide drug candidates, in collaboration with the group’s SBS-based peptide unit.

http://brimble.chem.auckland.ac.nz/?q=research

Drug discovery - new antibiotics based on novel aminoacid components

Natural Product Synthesis: Asymmetric Synthesis of Spiroketals


Supervisor

Distinguished Professor Margaret Brimble

Dr Dan Furkert

Discipline

Chemical Sciences

Project code: SCI043

Synthesis of spiroketals and spiroketal-containing natural products is a longstanding interest of our group. These molecular scaffolds, consisting of two (or sometimes even three) rings joined at a quaternary carbon with two bonds to oxygen, are found in a wide range of natural products that demonstrate interesting bioactivity. Some examples of our current and previous targets are shown (spiroketals highlighted in grey).

This research area offers a great opportunity to apply your organic chemistry background to natural product synthesis, building on our group’s particular expertise in spiroketals. Projects will based on stereoselective multistep organic synthesis, aiming to successfully prepare structures found in recently-isolated natural products. There will be a chance to learn a wide variety of classic and state-of-the-art chemistry techniques for asymmetric synthesis including catalysis, pericyclic reactions, aldol reactions and organometallic additions.

http://brimble.chem.auckland.ac.nz/?q=research

Natural product synthesis - asymmetic synthesis of spiroketals

Bioorganometallic Anticancer Chemotherapeutics: Preparation of Metal Complexes with Bioactive Ligands


Supervisor

Prof. Christian Hartinger

Discipline

Chemical Sciences

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. 

Design of Multimodal Organometallic Anticancer Agents


Supervisor

Prof. Christian Hartinger

Discipline

Chemical Sciences

Project code: SCI045

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.

Design and Applications of Organometallic Complexes for Catalysis


Supervisor

Prof. Christian Hartinger

Prof. James Wright

Discipline

Chemical Sciences

Project code: SCI046

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.

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


Supervisor

Prof. Christian Hartinger

Discipline

Chemical Sciences

Project code: SCI047

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 reaction products and/or binding kinetics. These studies are important to select compounds for further preclinical development.

Synthesis of biologically active lignan natural products


Supervisor

A/Prof David Barker

Discipline

Chemical Sciences

Project code: SCI048

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. 

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


Supervisor

A/Prof David Barker

Dr Johannes Reynisson

Discipline

Chemical Sciences

Project code: SCI049

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.

Exploring the effect of fluorination on Claisen rearrangement reactions


Supervisor

A/Prof David Barker

Discipline

Chemical Sciences

Project code: SCI050

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.

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


Supervisor

A/Prof David Barker

Dr Bruno Fedrizzi

Discipline

Chemical Sciences

Project code: SCI051

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.

Synthesis of novel polymeric materials as surface active antimicrobial agents


Supervisor

A/Prof David Barker

Prof Jadranka Travas-Sejdic

Discipline

Chemical Sciences

Project code: SCI052

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.

Synthesis of novel polymeric materials for modern electronic materials


Supervisor

A/Prof David Barker

Prof Jadranka Travas-Sejdic

Discipline

Chemical Sciences

Project code: SCI053

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.

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


Supervisor

Erin Leitao

Discipline

Chemical Sciences

Project code: SCI054

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.

Understanding the mechanism of copper-catalysed cross-coupling with main-group substrates


Supervisor

Erin Leitao

Discipline

Chemical Sciences

Project code: SCI055

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.

Catalytic routes to robust polysilanes


Supervisor

Erin Leitao

Discipline

Chemical Sciences

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. Inorganic synthesis including characterization using NMR spectroscopy and GC-MS will be learned.

Surfaces for Dynamic Microfluidics


Supervisor

Geoff Willmott

Discipline

Chemical Sciences

Project code: SCI057

Experimental projects are available in which surfaces are chemically altered in order to control their interactions with adjacent, moving fluids. High-speed photography is an important tool for characterizing the fluid flows. Examples of surfaces to functionalize include (i) spherical beads, which may be asymmetrically coated to create ‘Janus’ microparticles that self-assemble into interesting structures, (ii) capillary tubes, which are relevant to development of microfluidic devices, and (iii) substrates used on a quartz crystal microbalance. Suitable for chemistry students with good quantitative skills.

Behaviour of fingermarks on ice


Supervisor

Gordon Miskelly

Discipline

Chemical Sciences

Project code: SCI058

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.

Hyperspectral imaging in chemical and forensic analysis


Supervisor

Gordon Miskelly

Discipline

Chemical Sciences

Project code: SCI059

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 with time occur along one dimension or to systems that are of forensic interest.  This project will require calculations using the Matlab programming environment.

Development of novel inhibitors for Mycobacterium tuberculosis isocitrate lyase


Supervisor

Dr Ivanhoe Leung

A/Prof. Jonathan Sperry

Discipline

Chemical Sciences

Project code: SCI060

Tuberculosis (TB) is an infectious disease that is caused by Mycobacterium tuberculosis. The World Health Organisation (WHO) End TB Strategy aims to reduce the mortality rate by 90% and the incidence rate by 80% by 2030. As M. tuberculosis can only spread from people who have developed active pulmonary TB, treatment of latent TB infection for people from high risk groups is a viable strategy to control the spread of the disease. Current medication regimens to treat latent TB infection require high patient compliance. In addition, these drugs have high toxicity. The development of more effective and less toxic drugs to treat latent TB infection are therefore required if we are going to meet the goals set out by the WHO.

Isocitrate lyase (ICL) is a metabolic enzyme of Mycobacterium tuberculosis that is important for the survival of the bacteria in the latent state. We are interested in the development of novel ICL inhibitors. This summer scholarship will form an integral part of this project, which will include the design and synthesis of ICL inhibitors, and in vitro characterisation of their inhibition potency against different isoforms of Mycobacterium tuberculosis ICL using biophysical techniques.

There is no formal prerequisites, although a keen interest in organic and medicinal chemistry and an enthusiasm in enzymology will be helpful. Training and supervision will be given throughout the summer period by both Dr Leung and A/Prof. Sperry. Please contact us by email if you require any more information.

References:

Bhusal, R.P.; Bashiri, G.; Kwai, B.X.C.; Sperry, J.; Leung, I.K.H. Targeting isocitrate lyase for the treatment of latent tuberculosis. Drug Discov Today 2017, DOI: 10.1016/j.drudis.2017.04.012

Recombinant protein expression and purification


Supervisor

Dr Ivanhoe Leung

Discipline

Chemical Sciences

Project code: SCI061

Our group is interested in the applications of biophysical techniques to study proteins and enzymes that are important for (1) human health and disease, and (2) New Zealand’s agricultural industry.

A key step for any biophysical studies of proteins and enzymes involves the production and purification of recombinant proteins. In this project, you will be responsible for molecular cloning, conduct protein expression trials, optimise protein purification procedure and use biophysical tools including mass spectrometry and nuclear magnetic resonance spectroscopy to characterise the recombinant protein that you made.

There is no formal prerequisites to this summer scholarship, although an understanding of basic molecular biology and an enthusiasm in enzymology will be helpful. The work will be highly relevant to CHEM 350 and CHEM 390 in Stage 3. 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. 

Example of recent work from my group (including contribution from summer student):

Huang, R.; Ayine-Tora, D. M.; Muhammad Rosdi, M. N.; Li, Y.; Reynisson, J.; Leung, I. K. H. Virtual screening and biophysical studies lead to HSP90 inhibitors. Bioorg. Med. Chem. Lett. 2017, 27, 277–281.

Mechanistic and mutagenesis studies of grape (Vitis vinifera) polyphenol oxidase


Supervisor

Dr Ivanhoe Leung

Discipline

Chemical Sciences

Project code: SCI062

Polyphenol oxidases (PPOs) are type 3 di-copper enzymes that are widely found in both prokaryotes and eukaryotes. There are two main types of PPOs, including tyrosinase and catechol oxidase. Tyrosinase catalyses the oxidation of both monophenols and ortho-diphenols, whilst catechol oxidase only catalyses the oxidation of ortho-diphenols.

A number of structural and mechanistic studies were conducted in the last decade in order to understand the substrate selectivity of tyrosinase and catechol oxidase. Two proposals have emerged: One suggests the presence of a bulky ‘blocker’ residue above CuA may restrict PPO’s monophenolase activity, whilst the other suggests that the amino acid residues that govern the entry of the substrate(s) to the active site are more important for selectivity. To date, the differences in substrate selectivity between these two closely related enzymes are still not fully understood.

By using grape (Vitis vinifera) PPO as a model system, we hope to understand the structural and mechanistic basis of PPO substrate selectivity. This summer scholarship will form an integral part of this project, which will include the design and production of mutant PPO, and in vitro kinetic characterisation of different substrates using biophysical techniques.

There is no formal prerequisites to this summer scholarship, although an understanding of basic molecular biology and an enthusiasm in enzymology will be helpful. The work will be highly relevant to CHEM 350 and CHEM 390 in Stage 3. 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:

  1. M. Goldfeder, M. Kanteev, S. Isaschar-Ovdat, N. Adir, A. Fishman, Determination of tyrosinase substrate-binding modes reveals mechanistic differences between type-3 copper proteins, Nat. Commun. 5 (2014) 4505.
  2. A. Bijelic, M. Pretzler, C. Molitor, F. Zekiri, A. Rompel, The structure of a plant tyrosinase from walnut leaves reveals the importance of “substrate-guiding residues” for enzymatic specificity, Angew. Chem. Int. Ed. 54 (2015) 14677–14680.
  3. E. Solem, F. Tuczek, H. Decker, Tyrosinase versus catechol oxidase: one asparagine makes the difference, Angew. Chem. Int. Ed. 55 (2016) 2884–2888.

Atomic force microscopy on polymers


Supervisor

Lenny Voorhaar

Jadranka Travas-Sejdic

Discipline

Chemical Sciences

Project code: SCI063

In this project, the student will study polymeric structures using atomic force microscopy (AFM). AFM is a technique that used to look at nanometer scale structures. Different types of polymers, such as block copolymers and graft copolymers, can form different structures depending on how the samples are prepared. For example, spincoating a diblock copolymer can lead to micelles with either of the two polymer blocks inside the core, depending on which solvent is used. This will give us more information on the behaviour and properties of our polymers.

Skills required: basic knowledge on polymers, steady hands are needed to operate the AFM 

Electrospinning conducting elastomers


Supervisor

Jadranka Travas-Sejdic

Thomas Kerr-Phillips

Discipline

Chemical Sciences

Project code: SCI064

This project aims to develop novel electrospun conducting, chemically modified rubbers, followed by the incorporation of conducting polymers and characterisation of the materials by means of electron microscopies, electrochemistry and mechanical testing.

Metallabenzenes as building blocks for new materials


Supervisor

Prof. L. James Wright

Discipline

Chemical Sciences

Project code: SCI065

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.    

Water purification by catalytic oxidation of pollutants


Supervisor

Prof. L. James Wright

Discipline

Chemical Sciences

Project code: SCI066

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. 

CO-Releasing Molecules with Targeted Pharmacological Activity


Supervisor

Prof. L. James Wright

Prof C. Hartinger

Discipline

Chemical Sciences

Project code: SCI067

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.

Correlation between predicted and measured hydrogen bonding energies in model systems


Supervisor

Jóhannes Reynisson

Discipline

Chemical Sciences

Project code: SCI068

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

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


Supervisor

Jóhannes Reynisson

Discipline

Chemical Sciences

Project code: SCI069

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

The physicochemical parameters of veterinary drugs. A comparison study


Supervisor

Jóhannes Reynisson

Discipline

Chemical Sciences

Project code: SCI070

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

New Chemical Technologies for the Depolymerisation of Lignin


Supervisor

Associate Professor Jonathan Sperry

Discipline

Chemical Sciences

Project code: SCI071

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

Sustainable Medicinal Chemistry with Biomass-Derived Building Blocks


Supervisor

Associate Professor Jonathan Sperry

Discipline

Chemical Sciences

Project code: SCI072

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

Novel Synthetic Methods for Indole Construction


Supervisor

Associate Professor Jonathan Sperry

Discipline

Chemical Sciences

Project code: SCI073

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

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


Supervisor

Associate Professor Jonathan Sperry

Discipline

Chemical Sciences

Project code: SCI074

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)

Zwitterionic Materials for Enhanced Molecular Self-Assembly in Organic Solar Cells


Supervisor

Paul Hume

Discipline

Chemical Sciences

Project code: SCI075

Among the current options available for solar energy production, organic solar cells (OSCs) show considerable potential for development due to their low material costs and compatibility with high‑throughput production techniques.

The goal of this work is to prepare novel zwitterionic materials with potential for use in organic solar cells. It is hoped that these materials will lead to improved solar cell performance through supramolecular self‑assembly.

The precise arrangement of molecules in OSCs is a vital factor influencing performance. In particular, the relative positions of p‑p stacked molecules has a large effect on charge transport in OSCs. However, precise control over the lateral displacement between molecules is difficult to achieve. A novel way to achieve such control would be to “lock” the molecules relative to one another by the introduction of specific interactions acting parallel to the p-p stacking direction. It is hoped that zwitterionic materials would satisfy this requirement, controlling the lateral displacement of the planar aromatic units by local electrostatic forces. The compounds investigated will be based on 1,4‑diketopyrrolopyrrole (DPP). This well-studied chromophore is known to exhibit favourable photo-physical properties and is chemically and thermally stable under the conditions required for OSC fabrication.

This project will involve the synthesis of novel zwitterionic materials and characterisation of their electrochemical, optical and structural properties.

Characterisation of beverage antioxidants using cyclic voltammetry


Supervisor

Prof Paul Kilmartin

Discipline

Chemical Sciences

Project code: SCI076

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.

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


Supervisor

Prof Paul Kilmartin

Discipline

Chemical Sciences

Project code: SCI077

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.

Lighting up sugars – fluorescent probes for mono-saccharides


Supervisor

Prof Penny Brothers

Dr David Ware

Discipline

Chemical Sciences

Project code: SCI078

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, focussing on monosaccharides.

Activities: chemical synthesis and spectroscopy

Skills: Stage 2 or 3 organic or inorganic chemistry

Lighting up sugars – fluorescent probes for mono-saccharides

Lighting up sugars – fluorescent probes for poly-saccharides


Supervisor

Prof Penny Brothers

Dr David Ware

Discipline

Chemical Sciences

Project code: SCI079

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, focussing on polysaccharides.

Activities: chemical synthesis and spectroscopy

Skills: Stage 2 or 3 organic or inorganic chemistry

Lighting up sugars – fluorescent probes for poly-saccharides

Porphyrin compounds for dye sensitised solar cells


Supervisor

Prof Penny Brothers

Dr Duncan McGillivray

Discipline

Chemical Sciences

Project code: SCI080

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.  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

Porphyrin compounds for dye sensitised solar cells

Porphyrin compounds for new functional materials


Supervisor

Prof Penny Brothers

Dr David Ware

Prof David Williams

Discipline

Chemical Sciences

Project code: SCI081

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.  In this project they are investigated as the active site in gas sensors, and for their ability to act as building blocks in new functional electronic 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

Porphyrin compounds for new functional materials

Cobalt complexes for catalytic hydrogen production


Supervisor

Prof Penny Brothers

Dr David Ware

Dr Geoff Waterhouse

Discipline

Chemical Sciences

Project code: SCI082

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

Cobalt complexes for catalytic hydrogen production

The stability of microencapsulated cranberry powder


Supervisor

A/Prof Siew Young Quek

Discipline

Chemical Sciences

Project code: SCI083

This project will evaluate the stability of microencapsulated cranberry powder during storage, to verify if the method used is a satisfactory technique for the protection of the functional compounds in cranberry. The retention of anthocyanin, total phenolics and antioxidant activities will be evaluated after microencapsulation and during storage trials at different temperatures and relative humidity.

Applicant should have background in Food Science or Chemical Sciences, with chemical analysis skills and experience working in the lab environment. The project will start in November and estimated to last for about 3 months.

New Enzymes for Water Treatment


Supervisor

Dr Viji Sarojini
Prof James Wright

Discipline

Chemical Sciences

Project code: SCI248

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.

Anti-Biofilm Peptides for Water Disinfection


Supervisor

Dr Viji Sarojini

Prof James Wright

Discipline

Chemical Sciences

Project code: SCI249

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.

Antifreeze Peptides for Preserving Texture in Frozen Foods


Supervisor

Dr Viji Sarojini

Discipline

Chemical Sciences

Project code: SCI250

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 the University of Auckland. 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.

Lipopeptides with Broad Spectrum Antimicrobial and Antibiofilm Activities


Supervisor

Dr Viji Sarojini

Discipline

Chemical Sciences

Project code: SCI251

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.

Cell Penetrating Peptide Nanoparticles for Drug Delivery


Supervisor

Dr Viji Sarojini

Prof Jadranka Travas-Sejdic

Discipline

Chemical Sciences

Project code: SCI252

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. The summer student working in this project will be trained in Solid Phase Peptide Synthesis, HPLC purification and spectroscopic techniques such as NMR and Circular Dichroism and nanoparticle synthesis and analyses.

Antimicrobial Peptides against Food Spoiling Psychrophiles


Supervisor

Dr Viji Sarojini

A/P Siew-Young Quek

Discipline

Chemical Sciences

Project code: SCI253

Psychrophilic bacteria are cold-adapted organisms, found widely over the earth’s surface due to the vast number of habitats in which they can grow. Psychrophilic bacteria have also been found to grow in refrigerators, which is of great concern to the food industry. In particular, meat products have been found to be affected and spoiled by psychrophilic growth. An important psychrophile is the species Clostridium estertheticum, which has been found to cause blown pack meat spoilage in chilled vacuum-packed meat products. As New Zealand has a prominent meat industry, in particular of beef and lamb exports, targeting psychrophilic species such as C. estertheticum would be economically beneficial. This project will explore the potential of naturally produced antimicrobial peptides of the ice fish Chionodraco hamatus to inhibit the growth of Clostridium estertheticum in meat products. Promising peptide analogues will be used in combination with food packaging technologies in collaboration with A/P Quek, Director of the Food Science Programme. The summer student working in this project will be trained in Solid Phase Peptide Synthesis, HPLC purification, anti-bacterial and anti-biofilm assays, microscopy techniques as well as spectroscopic techniques such as NMR and Circular Dichroism.

De novo Designed Models of Protein ß-sheets


Supervisor

Dr Viji Sarojini

Prof Juliet Gerrard

Discipline

Chemical Sciences

Project code: SCI254

The remarkable biological functions exhibited by proteins depend on the ability of the flexible peptide chains to fold into well-ordered and compact structures that originate with distinct secondary structural elements like alpha-helices and beta-sheets discovered by Linus Pauling half a century ago. Thus, the de novo design of protein secondary structures is an important step towards understanding the biological functions of proteins in living cells. Amongst the protein secondary structural elements, beta-sheets (aggregates of beta hairpins) are particularly interesting, since they ensure not only protein function but also mis-function as in the case of amyloid plaque formation in Alzheimer’s disease. This project aims to understand the factors that modulate the formation and stability of beta-sheets which are not well understood. Survey of the various peptidic and non-peptidic structures that promote chain reversals in proteins will be followed by the incorporation of selected structures in short synthetic peptides by Solid Phase Peptide Synthesis techniques. The ability of the peptides to fold into the desired beta-hairpin fold as well as its propensity to aggregate into higher order structures will be investigated using multi-dimensional NMR and circular dichroism (CD) The summer student working in this project will be trained in Synthetic Organic Chemistry, Solid Phase Peptide Synthesis, HPLC, NMR and CD.