Synthesis and biological activity of ajoenes with increased aqueous solubility

 

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dc.contributor.advisor Hunter, Roger en_ZA
dc.contributor.author Mabunda,Mandla en_ZA
dc.date.accessioned 2014-08-22T10:39:35Z
dc.date.available 2014-08-22T10:39:35Z
dc.date.issued 2013 en_ZA
dc.identifier.uri http://hdl.handle.net/11427/6674
dc.description.abstract The synthesis of four new ajoene analogues is presented in this thesis. The key to the synthesis was gaining access to a phenol derivative containing the ajoene core structure (sulfoxide / vinyl disulfide) that could be functionalised with various substituents. Evaluation of biological activity returned excellent in vitro activity against a WHCO1 oesophageal cell-line, in which a derivative with a methoxycarbonylmethylene substituent (PMB-ester) was shown to be the most active analogue that was fifteen times more active than Z-ajoene with an IC50 of 1.7 M. An aqueous solubility assay reveals that aqueous solubility increased with subsituition and the analogues with amido or acetate substituents were the most soluble ones. The analogues were also shown to enhance the apoptotic effects of two chemotherapeutic drugs Doxorubicin and Vincristine via chemosensitization. This effect was attributed to the presence of at least one p-methoxybenzyl substituent in the structure. en_ZA
dc.language.iso eng en_ZA
dc.title Synthesis and biological activity of ajoenes with increased aqueous solubility en_ZA
dc.type Thesis / Dissertation en_ZA
uct.type.publication Research en_ZA
uct.type.resource Thesis en_ZA
dc.publisher.institution University of Cape Town
dc.publisher.faculty Faculty of Science en_ZA
dc.publisher.department Department of Chemistry en_ZA
dc.type.qualificationlevel Masters en_ZA
dc.type.qualificationname MSc en_ZA
uct.type.filetype Text
uct.type.filetype Image


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