In vitro studies of dermally absorbed Cu(II) tripeptide complexes as potential anti-inflammatory drugs

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dc.contributor.advisorJackson, Graham Ellisen_ZA
dc.contributor.authorVicatos, Giselle Men_ZA
dc.date.accessioned2016-07-20T07:01:34Z
dc.date.available2016-07-20T07:01:34Z
dc.date.issued2016en_ZA
dc.description.abstractCopper(II) complexes have anti-inflammatory properties which can alleviate the symptoms of rheumatoid arthritis (RA) and thus control the progression of the disease. In this study two tripeptides, namely sarcosyl-L-leucyl-phenylalanine (Sar-Leu-Phe) and glycyl-L-leucyl-phenylalanine (Gly-Leu-Phe) were studied as potential chelators, which would increase the bioavailability of copper(II) through dermal absorption. Glass electrode potentiometry was used to measure the solution thermodynamics of copper(II), nickel(II) and zinc(II) with Gly-Leu-Phe and Sar-Leu-Phe, at 25 0.01 °C and an ionic strength of 0.15 M (NaCl). The terminal amine of both tripeptides was found to have the same basicity, but the methyl group on the terminal amine decreased the stability constants of the copper(II) ligand species by 0.38 to 1.67 log units. It increased the stability constants of the zinc(II) ligand species by 0.13 to 1.07 log units and it also increased the stability constant of the NiL2H-1 species by 1.3 to 1.4 log units, while not affecting the NiL species. The solution structures of the complexes were determined spectroscopically using Ultraviolet-visible spectrophotometry, Infrared spectroscopy and 1H NMR spectroscopy. The copper(II) complexes tend more towards a square planar geometry, rather than the expected tetragonally distorted octahedral geometry. All the nickel(II) species, were square planar, except for the ML species, which was octahedral. The ligand coordinated to the metal ion via an amine-N, two amide-Ns, two carbonyl-Os and a carboxyl-O. The postulated coordination modes were validated using quantum mechanical calculations. Two methods were used to study percutaneous skin absorption, namely octanol/water partition coefficients and Franz cell permeation.en_ZA
dc.identifier.apacitationVicatos, G. M. (2016). <i>In vitro studies of dermally absorbed Cu(II) tripeptide complexes as potential anti-inflammatory drugs</i>. (Thesis). University of Cape Town ,Faculty of Science ,Department of Chemistry. Retrieved from http://hdl.handle.net/11427/20499en_ZA
dc.identifier.chicagocitationVicatos, Giselle M. <i>"In vitro studies of dermally absorbed Cu(II) tripeptide complexes as potential anti-inflammatory drugs."</i> Thesis., University of Cape Town ,Faculty of Science ,Department of Chemistry, 2016. http://hdl.handle.net/11427/20499en_ZA
dc.identifier.citationVicatos, G. 2016. In vitro studies of dermally absorbed Cu(II) tripeptide complexes as potential anti-inflammatory drugs. University of Cape Town.en_ZA
dc.identifier.ris TY - Thesis / Dissertation AU - Vicatos, Giselle M AB - Copper(II) complexes have anti-inflammatory properties which can alleviate the symptoms of rheumatoid arthritis (RA) and thus control the progression of the disease. In this study two tripeptides, namely sarcosyl-L-leucyl-phenylalanine (Sar-Leu-Phe) and glycyl-L-leucyl-phenylalanine (Gly-Leu-Phe) were studied as potential chelators, which would increase the bioavailability of copper(II) through dermal absorption. Glass electrode potentiometry was used to measure the solution thermodynamics of copper(II), nickel(II) and zinc(II) with Gly-Leu-Phe and Sar-Leu-Phe, at 25 0.01 °C and an ionic strength of 0.15 M (NaCl). The terminal amine of both tripeptides was found to have the same basicity, but the methyl group on the terminal amine decreased the stability constants of the copper(II) ligand species by 0.38 to 1.67 log units. It increased the stability constants of the zinc(II) ligand species by 0.13 to 1.07 log units and it also increased the stability constant of the NiL2H-1 species by 1.3 to 1.4 log units, while not affecting the NiL species. The solution structures of the complexes were determined spectroscopically using Ultraviolet-visible spectrophotometry, Infrared spectroscopy and 1H NMR spectroscopy. The copper(II) complexes tend more towards a square planar geometry, rather than the expected tetragonally distorted octahedral geometry. All the nickel(II) species, were square planar, except for the ML species, which was octahedral. The ligand coordinated to the metal ion via an amine-N, two amide-Ns, two carbonyl-Os and a carboxyl-O. The postulated coordination modes were validated using quantum mechanical calculations. Two methods were used to study percutaneous skin absorption, namely octanol/water partition coefficients and Franz cell permeation. DA - 2016 DB - OpenUCT DP - University of Cape Town LK - https://open.uct.ac.za PB - University of Cape Town PY - 2016 T1 - In vitro studies of dermally absorbed Cu(II) tripeptide complexes as potential anti-inflammatory drugs TI - In vitro studies of dermally absorbed Cu(II) tripeptide complexes as potential anti-inflammatory drugs UR - http://hdl.handle.net/11427/20499 ER - en_ZA
dc.identifier.urihttp://hdl.handle.net/11427/20499
dc.identifier.vancouvercitationVicatos GM. In vitro studies of dermally absorbed Cu(II) tripeptide complexes as potential anti-inflammatory drugs. [Thesis]. University of Cape Town ,Faculty of Science ,Department of Chemistry, 2016 [cited yyyy month dd]. Available from: http://hdl.handle.net/11427/20499en_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.titleIn vitro studies of dermally absorbed Cu(II) tripeptide complexes as potential anti-inflammatory drugsen_ZA
dc.typeMaster Thesis
dc.type.qualificationlevelMasters
dc.type.qualificationnameMScen_ZA
uct.type.filetypeText
uct.type.filetypeImage
uct.type.publicationResearchen_ZA
uct.type.resourceThesisen_ZA
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