Supramolecular derivatives of selected bioactive compounds : a physicochemical study

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dc.contributor.advisorCaira, Mino Ren_ZA
dc.contributor.advisorBourne, Susanen_ZA
dc.contributor.authorSamsodien, Halimaen_ZA
dc.date.accessioned2014-08-13T14:29:52Z
dc.date.available2014-08-13T14:29:52Z
dc.date.issued2010en_ZA
dc.descriptionIncludes abstract.en_ZA
dc.descriptionIncludes bibliographical references (p. 270-271).en_ZA
dc.description.abstractThe author’s objective was to prepare new solid phases of three bioactive compounds: the steroidal anticancer agent 2-methoxyestradiol [polymorphs and cyclodextrin (CD) inclusion complexes], its derivative 2-methoxyestradiol-bis-sulfamate (polymorphs), and the antiretroviral agent, nevirapine (co-crystals). The solubility and dissolution profiles of the three compounds and those of selected ‘supramolecularly-derived’ species were also assessed. Three distinct phases of 2-methoxyestradiol (2ME) were successfully isolated, the most stable form (a polymorph) by the recrystallisation method, an amorph by melt studies and a solvated form by recrystallisation. 2-methoxyestradiol-bis-sulfamate (2MES), in the form of a hemihydrate, remained unchanged when recrystallised from various solvents. Several CDs were used for possible 2-methoxyestradiol inclusion; these were α-, β -,γ-CD, and nine derivatised cyclodextrins. Co-precipitation and kneading techniques were employed in attempts to produce inclusion complexes. An inclusion complex of 2ME was isolated with each of the following: -CD, HPBCD, RAMEB, DIMEB and TRIMEB. Co-crystallisation of nevirapine was attempted using twelve potential co-formers with GRAS status. Two co-crystals, one with saccharin and one with rac-tartaric acid, were isolated by the co-precipitation method. Physicochemical characterisation techniques used to assess the thermal behaviour of the products included hot stage microscopy, differential scanning calorimetry and thermogravimetric analysis. UV spectrophotometry and elemental analysis were used for hostguest stoichiometric assay and purity determination respectively. X-ray powder diffraction and single crystal X-ray structure determination were used for structural analysis.en_ZA
dc.identifier.apacitationSamsodien, H. (2010). <i>Supramolecular derivatives of selected bioactive compounds : a physicochemical study</i>. (Thesis). University of Cape Town ,Faculty of Science ,Department of Chemistry. Retrieved from http://hdl.handle.net/11427/6360en_ZA
dc.identifier.chicagocitationSamsodien, Halima. <i>"Supramolecular derivatives of selected bioactive compounds : a physicochemical study."</i> Thesis., University of Cape Town ,Faculty of Science ,Department of Chemistry, 2010. http://hdl.handle.net/11427/6360en_ZA
dc.identifier.citationSamsodien, H. 2010. Supramolecular derivatives of selected bioactive compounds : a physicochemical study. University of Cape Town.en_ZA
dc.identifier.ris TY - Thesis / Dissertation AU - Samsodien, Halima AB - The author’s objective was to prepare new solid phases of three bioactive compounds: the steroidal anticancer agent 2-methoxyestradiol [polymorphs and cyclodextrin (CD) inclusion complexes], its derivative 2-methoxyestradiol-bis-sulfamate (polymorphs), and the antiretroviral agent, nevirapine (co-crystals). The solubility and dissolution profiles of the three compounds and those of selected ‘supramolecularly-derived’ species were also assessed. Three distinct phases of 2-methoxyestradiol (2ME) were successfully isolated, the most stable form (a polymorph) by the recrystallisation method, an amorph by melt studies and a solvated form by recrystallisation. 2-methoxyestradiol-bis-sulfamate (2MES), in the form of a hemihydrate, remained unchanged when recrystallised from various solvents. Several CDs were used for possible 2-methoxyestradiol inclusion; these were α-, β -,γ-CD, and nine derivatised cyclodextrins. Co-precipitation and kneading techniques were employed in attempts to produce inclusion complexes. An inclusion complex of 2ME was isolated with each of the following: -CD, HPBCD, RAMEB, DIMEB and TRIMEB. Co-crystallisation of nevirapine was attempted using twelve potential co-formers with GRAS status. Two co-crystals, one with saccharin and one with rac-tartaric acid, were isolated by the co-precipitation method. Physicochemical characterisation techniques used to assess the thermal behaviour of the products included hot stage microscopy, differential scanning calorimetry and thermogravimetric analysis. UV spectrophotometry and elemental analysis were used for hostguest stoichiometric assay and purity determination respectively. X-ray powder diffraction and single crystal X-ray structure determination were used for structural analysis. DA - 2010 DB - OpenUCT DP - University of Cape Town LK - https://open.uct.ac.za PB - University of Cape Town PY - 2010 T1 - Supramolecular derivatives of selected bioactive compounds : a physicochemical study TI - Supramolecular derivatives of selected bioactive compounds : a physicochemical study UR - http://hdl.handle.net/11427/6360 ER - en_ZA
dc.identifier.urihttp://hdl.handle.net/11427/6360
dc.identifier.vancouvercitationSamsodien H. Supramolecular derivatives of selected bioactive compounds : a physicochemical study. [Thesis]. University of Cape Town ,Faculty of Science ,Department of Chemistry, 2010 [cited yyyy month dd]. Available from: http://hdl.handle.net/11427/6360en_ZA
dc.language.isoengen_ZA
dc.publisher.departmentDepartment of Chemistryen_ZA
dc.publisher.facultyFaculty of Scienceen_ZA
dc.publisher.institutionUniversity of Cape Town
dc.subject.otherChemistryen_ZA
dc.titleSupramolecular derivatives of selected bioactive compounds : a physicochemical studyen_ZA
dc.typeDoctoral Thesis
dc.type.qualificationlevelDoctoral
dc.type.qualificationnamePhDen_ZA
uct.type.filetypeText
uct.type.filetypeImage
uct.type.publicationResearchen_ZA
uct.type.resourceThesisen_ZA
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