Research Guides

Department of Chemistry University of Oxford

Professor M.G. Moloney

My interests are concerned with the application of organic chemistry to the synthesis of biologically relevant compounds and the functionalisation of materials.

Synthesis of Bioactive Compound Libraries

Natural products exhibit wide biological activities, and therefore provide inspiration for the development of new drugs and medicinally active compounds.  An important subset contain pyrrolidine and piperidine rings as a core structure, and are of considerable importance because of their antibiotic, antibacterial, antifungal and anticancer properties. We have developed synthetic methodology allowing simple, short, efficient and versatile access to such heterocycles based upon the manipulation of bicyclic ring templates, which allows control of both relative and absolute stereochemistry, and moreover gives several points of diversity on the ring periphery for further derivatisation. Current efforts focus on the application of this methodology for the rapid preparation of chiral heterocyclic libraries for the identification of new antibacterials and anticancer agents.

Functionalisation of Materials

We have developed technology for the chemical modification of material surfaces under mild conditions; it permits the introduction of useful functionality on to what would otherwise be considered to be inert materials and gives a chemically irreversible modification to the polymer. We have shown that highly reactive diarylcarbene intermediates, easily generated under thermolytic or photolytic conditions, can be used for the modification of a wide variety of polymers, including natural (cotton) as well as synthetic materials (polystyrene, polyethylene, polyethyleneterephthalate, nylon as well as low surface energy materials such as polypropylene and PTFE), to introduce a range of surface activity, including colour, fluorescence, hydrophilicity/hydrophobicity, antibacterial function and adhesive modifications. The methodology is intrinsically flexible, being applicable to powders, beads, films and sheets, as well as woven and non-woven fabrics. The modification leads to a surface coverage of 5-20% of the surface area, but is not a simple molecular monolayer; rather it extends to the nano-dimension, but does not lead to surface film formation, surface degradation or other visible change in the material surface. Current research effort is focused on elaboration on the technology for different macroscopic effects, and for the control of the material interface with biological systems, suitable for application in biomedical devices, sensors and implants.

 

Publications related to bioactive compounds:

Tetramic acids as bioactive templates: synthesis, tautomeric and antibacterial behaviour”, Y.-C. Jeong, and M.G. Moloney, Synlett., 2009, 2487-2491.

Oxazolomycins: Lead Structures for Novel Antibiotics by Click Hybridisation”, C.L. Bagwell and M.G. Moloney, Bioorg. Med Chem. Lett., 2010, 20, 2090–2094.

"Enantioselective Synthesis of Tetramic Acids and Lactams from Threonine and their Antibiotic Activity", M. Anwar and M.G. Moloney, Tetrahedron:Asymmetry, 2010, 21, 1758–1770.

“A rapid entry to the polycyclic core of isatisine”, C.J. Matthews, M.G. Moloney, A. Thompson, H. Winiarska and H. Winney, Synlett., 2011, 378-382.

“Synthesis of and tautomerism in 3-acyltetramic acids, Y.-C. Jeong, and M.G. Moloney, J. Org. Chem., 2011, 76,1342-1354.

"Synthesis and Evaluation of the Antibacterial Activity of the Functionalised Pyroglutamate Core of the Oxazolomycins", S. Chau, P.J. Fryer, M.G. Moloney and P.C. Trippier,. Org. Biomol. Chem., 2012, 10, 3472.

Publications related to functional materials:

Functionalised Polymers By Chemical Surface Modification,” M. G. Moloney, J. Phys. D: Appl. Phys., 2008, 41, 174006.

“Direct introduction of phosphonate by the surface modification of polymers enhances biocompatibility,” C. Chong, J.-P. Griffiths, M. G. Moloney, J. Triffitt and D. Swallow, Reactive and Functional Polymers, 2009, 69, 77–85.

“Surface Functional Polymers by Post-Polymerization Modification using Diarylcarbenes: Introduction, Release and Regeneration of Hydrogen Peroxide and Bactericidal Activity”, J.-P. Griffiths, B. Maliha, M. G. Moloney, and A. L. Thompson and I. Hussain, Langmuir, 2010, 26, 14142–14153.

"Post Polymerisation Modification of Surface Chemical Functionality and its Effect on Protein Binding", C. Choong, J. Foord, J.P. Griffiths, E.M. Parker, L. Baiwen, M. Bora and M.G. Moloney, New J. Chem., 2012, 36, 1187-1200.