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Synthesis and biological activity of ajoenes with increased aqueous solubility
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 retu...
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| Format: | Thesis |
| Language: | English |
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Department of Chemistry
2014
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| _version_ | 1867613334248882176 |
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| access_status_str | Open Access |
| author | Mabunda,Mandla |
| author2 | Hunter, Roger |
| author_browse | Hunter, Roger Mabunda,Mandla |
| author_facet | Hunter, Roger Mabunda,Mandla |
| author_sort | Mabunda,Mandla |
| collection | Thesis |
| description | 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. |
| format | Thesis |
| id | oai:open.uct.ac.za:11427/6674 |
| institution | University of Cape Town (South Africa) |
| language | eng |
| last_indexed | 2026-06-10T12:34:28.941Z |
| license_str | Not specified — see source repository |
| provenance_str_mv | Harvested via OAI-PMH from UCTD — University of Cape Town Open Access Repository |
| publishDate | 2014 |
| publishDateRange | 2014 |
| publishDateSort | 2014 |
| publisher | Department of Chemistry |
| publisherStr | Department of Chemistry |
| record_format | dspace |
| source_str | UCTD — University of Cape Town Open Access Repository |
| spelling | oai:open.uct.ac.za:11427/6674 Synthesis and biological activity of ajoenes with increased aqueous solubility Mabunda,Mandla Hunter, Roger 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. 2014-08-22T10:39:35Z 2014-08-22T10:39:35Z 2013 Master Thesis Masters MSc http://hdl.handle.net/11427/6674 eng application/pdf Department of Chemistry Faculty of Science University of Cape Town |
| spellingShingle | Mabunda,Mandla Synthesis and biological activity of ajoenes with increased aqueous solubility |
| thesis_degree_str | Master's |
| title | Synthesis and biological activity of ajoenes with increased aqueous solubility |
| title_full | Synthesis and biological activity of ajoenes with increased aqueous solubility |
| title_fullStr | Synthesis and biological activity of ajoenes with increased aqueous solubility |
| title_full_unstemmed | Synthesis and biological activity of ajoenes with increased aqueous solubility |
| title_short | Synthesis and biological activity of ajoenes with increased aqueous solubility |
| title_sort | synthesis and biological activity of ajoenes with increased aqueous solubility |
| url | http://hdl.handle.net/11427/6674 |
| work_keys_str_mv | AT mabundamandla synthesisandbiologicalactivityofajoeneswithincreasedaqueoussolubility |