Computer aided chemical speciation in designing metal-based potential anti-inflammatory agents

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dc.contributor.advisorJackson, Graham Ellisen_ZA
dc.contributor.authorOdisitse, Sebusien_ZA
dc.date.accessioned2014-08-13T14:29:18Z
dc.date.available2014-08-13T14:29:18Z
dc.date.issued2006en_ZA
dc.descriptionIncludes bibliographical references (leaves 158-161).en_ZA
dc.description.abstractThe objective of this study was to develop copper based anti-inflammatory agents for the treatment of inflammation associated with Rheumatoid Arthritis. Four low molecular ligands, N,Nt-di(aminoethylene)-2,6-pyridine dicarbonylamine (PrDH), Bis-(N,N-dimethylethyl)-2,6-pyridinedicarboxamide (PrDM), N,N'-bis[2(2-pyridyl)-methyl]pyridine-2,6-dicarboxamide (PrDPr) and 3,5-bis[(aminoethyl)ethanediamide]-4-oxahexacyclo-dodecane (PCUA) were designed and synthesised. The formation constants of these ligands with H+, Cu2+, Niz+, Znz+ and Caz+ were determined potentiometrically at 25°C and 0.15 mol dm-3 Na+Cr. The Cu(II) formed relatively more stable complexes than other three metal ions. The structures of the different Cu(II) species formed with these ligands were investigated using nuclear magnetic resonance(NMR), infrared (IR) spectroscopy, ultraviolet-visible (UV-visible) spectroscopy as well as molecular mechanics calculations. For the NMR spectroscopy, results showed that the central pyridyl nitrogen and amide nitrogen(s) as well as the terminal amino/pyridyl groups coordinate to the Cu(II) ion in solution. The IR results indicated that an amide nitrogen is coordinated to the Cu(II). The UV-visible study gave the smooth deconvoluted spectra of the individual species for the Cu(II)-PrDH, Cu(II)-PrDM and Cu(II)-PrDPr systems in support of the potentiometric results. The three studied ligands form tetragonally distorted octahedral MLH-l and MLH-z species with Cu(II). The molecular mechanics was used to calculate the internal strain energies of the different possible geometries of related complex species. A comparison of these energies was used to rationalize the different stabilities of these structures.en_ZA
dc.identifier.apacitationOdisitse, S. (2006). <i>Computer aided chemical speciation in designing metal-based potential anti-inflammatory agents</i>. (Thesis). University of Cape Town ,Faculty of Science ,Department of Chemistry. Retrieved from http://hdl.handle.net/11427/6354en_ZA
dc.identifier.chicagocitationOdisitse, Sebusi. <i>"Computer aided chemical speciation in designing metal-based potential anti-inflammatory agents."</i> Thesis., University of Cape Town ,Faculty of Science ,Department of Chemistry, 2006. http://hdl.handle.net/11427/6354en_ZA
dc.identifier.citationOdisitse, S. 2006. Computer aided chemical speciation in designing metal-based potential anti-inflammatory agents. University of Cape Town.en_ZA
dc.identifier.ris TY - Thesis / Dissertation AU - Odisitse, Sebusi AB - The objective of this study was to develop copper based anti-inflammatory agents for the treatment of inflammation associated with Rheumatoid Arthritis. Four low molecular ligands, N,Nt-di(aminoethylene)-2,6-pyridine dicarbonylamine (PrDH), Bis-(N,N-dimethylethyl)-2,6-pyridinedicarboxamide (PrDM), N,N'-bis[2(2-pyridyl)-methyl]pyridine-2,6-dicarboxamide (PrDPr) and 3,5-bis[(aminoethyl)ethanediamide]-4-oxahexacyclo-dodecane (PCUA) were designed and synthesised. The formation constants of these ligands with H+, Cu2+, Niz+, Znz+ and Caz+ were determined potentiometrically at 25°C and 0.15 mol dm-3 Na+Cr. The Cu(II) formed relatively more stable complexes than other three metal ions. The structures of the different Cu(II) species formed with these ligands were investigated using nuclear magnetic resonance(NMR), infrared (IR) spectroscopy, ultraviolet-visible (UV-visible) spectroscopy as well as molecular mechanics calculations. For the NMR spectroscopy, results showed that the central pyridyl nitrogen and amide nitrogen(s) as well as the terminal amino/pyridyl groups coordinate to the Cu(II) ion in solution. The IR results indicated that an amide nitrogen is coordinated to the Cu(II). The UV-visible study gave the smooth deconvoluted spectra of the individual species for the Cu(II)-PrDH, Cu(II)-PrDM and Cu(II)-PrDPr systems in support of the potentiometric results. The three studied ligands form tetragonally distorted octahedral MLH-l and MLH-z species with Cu(II). The molecular mechanics was used to calculate the internal strain energies of the different possible geometries of related complex species. A comparison of these energies was used to rationalize the different stabilities of these structures. DA - 2006 DB - OpenUCT DP - University of Cape Town LK - https://open.uct.ac.za PB - University of Cape Town PY - 2006 T1 - Computer aided chemical speciation in designing metal-based potential anti-inflammatory agents TI - Computer aided chemical speciation in designing metal-based potential anti-inflammatory agents UR - http://hdl.handle.net/11427/6354 ER - en_ZA
dc.identifier.urihttp://hdl.handle.net/11427/6354
dc.identifier.vancouvercitationOdisitse S. Computer aided chemical speciation in designing metal-based potential anti-inflammatory agents. [Thesis]. University of Cape Town ,Faculty of Science ,Department of Chemistry, 2006 [cited yyyy month dd]. Available from: http://hdl.handle.net/11427/6354en_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.titleComputer aided chemical speciation in designing metal-based potential anti-inflammatory agentsen_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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