Synthesis, characterization and biological activities of photocorms derived from cyclopentadienyl iron dimer with organosulfur and organoselenium ligands / Gan Chun Hau

Gan , Chun Hau (2022) Synthesis, characterization and biological activities of photocorms derived from cyclopentadienyl iron dimer with organosulfur and organoselenium ligands / Gan Chun Hau. Masters thesis, Universiti Malaya.

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Abstract

Carbon monoxide releasing molecule (CORM) are well known for various biological activities but the efficacy and mode of activities are not fully understood. The objective of this research is to synthesize and evaluate the biological of diiron dimer photoCORMs. In this research, the conventional Schlenk techniques under an inert atmosphere of argon is used to synthesize and isolate the products. The reactions of [CpFe(CO)2]2 (1) with 2 moles equivalents of R2E2 (R= C6H11, C4H3S, CH2C6H5; E= S, Se) have yielded dinuclear products of [CpFe(CO)(μ-L)]2 (L= C6H11S (2), C4H3S2 (3) and CH2C6H5Se (4)), respectively. An additional trinuclear compound, C24H22O2Se2Fe3 (5) was isolated only from the reaction with dibenzyl diselenide. It was postulated that the formation of 2, 3, 4 and 5 proceeded via the radical pathway which involved the formation of CpFe(CO)2 • radical and S-S bond or Se-Se bond cleavages of the ligands. All the products have been fully characterized by FT-IR, 1H and 13C NMR, CHN elemental analysis, GCMS and structurally elucidated by single crystal X-ray diffraction. Since 5 was a minor product, it was not involved in any further study. The stability of 2-4 both under dark and UV conditions were investigated by monitoring the changes in their respective UV-Vis spectra in phosphate buffered saline (PBS) solution. Their potential application as photoCORMs were also evaluated by standard myoglobin assay. 3 showed the shortest half-life and highest equivalent of CO-released. The anticancer studies of 2-4 were evaluated in-vitro on breast cancer cell lines (MCF-7, MDA-MB-231 and MDA-MB-468) and the cytotoxicity of 3 had increased approximately 4 times against MDA-MB-468 cell line upon UV irradiation, which was 11.5 ± 2.7 μM. All complexes exhibited cytotoxic effect on specific sub-types of breast cancer cells. Antimalarial activities of 2-4 had also been studied and reported in this work. Unfortunately, these complexes did not display any significant effect on the Plasmodium falciparum 3D7 strains. The physicochemical, pharmacokinetics and drug like parameters of 2-4 were determined by using SwissADME tool.

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