Victoria University

Synthesis of Novel Pyran Fragments to Incorporate into Peloruside Analogues

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dc.contributor.advisor Teesdale-Spittle, Paul
dc.contributor.advisor Harvey, Joanne Bayley, Oliver 2019-05-01T23:52:57Z 2019-05-01T23:52:57Z 2019 2019
dc.description.abstract Cancer is currently the second largest cause of death globally, leading to a high demand for new and effective chemotherapeutics. For years, natural products have been used as a source of new bioactive compounds; of particular interest in this context, as a source of new chemotherapeutics. One chemotherapeutic candidate which has attracted significant attention in synthetic and medicinal chemistry communities, is peloruside A. Peloruside A is a bioactive secondary metabolite isolated from the New Zealand marine sponge Mycale hentscheli. Since its discovery, peloruside A has shown great promise in cancer studies both in vivo and in vitro with effects observed even at nanomolar concentrations. These chemotherapeutic effects have been shown to occur by halting cell division at the G2/M checkpoint via microtubule stabilisation. Of particular interest is that this stabilisation occurs in a manner distinct from that of the already established taxane class of microtubule stabilising drugs. This means that peloruside A is able to offer both inhibition of cell division in Taxol® resistant cells and synergistic inhibition alongside the current taxane drugs. Since peloruside A is not abundantly available from its natural source, there is a strong incentive for the development of new synthetic strategies for peloruside A production. Unfortunately attempts at aquaculture and attempts at developing an industrial scale synthesis have both proven unsuccessful thus far. In an attempt to overcome some of the difficulties with the scale up of peloruside, analogues have been developed that are intended to have similar bioactivity to peloruside A but simpler, more concise, synthetic routes. These analogues will also enable further elucidation of the binding properties of peloruside A. This project focuses on the generation of a functionalised pyran fragment, starting from a simple carbohydrate, that may be incorporated into the proposed analogues. en_NZ
dc.language.iso en_NZ
dc.publisher Victoria University of Wellington en_NZ
dc.subject Organic Synthesis en_NZ
dc.subject Drug Analogue en_NZ
dc.subject Peloruside en_NZ
dc.title Synthesis of Novel Pyran Fragments to Incorporate into Peloruside Analogues en_NZ
dc.type text en_NZ
vuwschema.contributor.unit School of Chemical and Physical Sciences en_NZ
vuwschema.contributor.unit Centre for Biodiscovery en_NZ
vuwschema.type.vuw Awarded Research Masters Thesis en_NZ Chemistry en_NZ Drug Development en_NZ Victoria University of Wellington en_NZ Masters en_NZ Master of Drug Discovery and Development en_NZ
dc.rights.license Author Retains Copyright en_NZ 2019-04-15T04:17:27Z
vuwschema.subject.anzsrcfor 030503 Organic Chemical Synthesis en_NZ
vuwschema.subject.anzsrctoa 3 APPLIED RESEARCH en_NZ

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