Synthesis, cytotoxicity and dna binding studies of ruthenium(ii) mixed-polypyridyl complexes

A series of ruthenium(II) complexes, including two novel compounds [Ru(dppz)2L]2+ where dppz = dipyrido-[3,2-a:2’,3’-c]phenazine, and L = 2-phenylimidazo[4,5- f][1,10]phenanthroline (PIP) or 2-(4-hydroxyphenyl)imidazo[4,5-f][1,10] phenanthroline (p-HPIP) have been synthesized and characterized. The...

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Main Author:	Harun, Siti Norain
Format:	Thesis
Language:	English
Published:	2015
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Online Access:	http://psasir.upm.edu.my/id/eprint/64862/1/FS%202015%2029IR.pdf
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spelling	my-upm-ir.648622018-07-31T04:10:08Z Synthesis, cytotoxicity and dna binding studies of ruthenium(ii) mixed-polypyridyl complexes 2015-03 Harun, Siti Norain A series of ruthenium(II) complexes, including two novel compounds [Ru(dppz)2L]2+ where dppz = dipyrido-[3,2-a:2’,3’-c]phenazine, and L = 2-phenylimidazo[4,5- f][1,10]phenanthroline (PIP) or 2-(4-hydroxyphenyl)imidazo[4,5-f][1,10] phenanthroline (p-HPIP) have been synthesized and characterized. The previously reported complexes [Ru(bpy)2L]2+ and [Ru(phen)2L]2+ were also prepared. All complexes were characterized by elemental analysis, 1H-NMR spectroscopy, ESI-Mass spectroscopy and FT-IR spectroscopy. The photophysical properties were analyzed by UV-Visible spectroscopy and fluorescence spectroscopy. [Ru(dppz)2PIP]2+ and [Ru(dppz)2p-HPIP]2+ displayed ‘molecular light-switch’ effect as they have high emission in acetonitrile but no emission in water. The cytotoxicity of all complexes against cancer cell lines Hela and MCF-7 were investigated through standard MTT assay. [Ru(dppz)2PIP]2+ showed moderate toxicity on both MCF-7 and Hela with IC50 of 37.64 µM and 28.02 µM, respectively. Interestingly, [Ru(dppz)2p-HPIP]2+ exhibited remarkable cytotoxicity results with IC50 of 13.52 µM on Hela and 11.63 µM on MCF- 7 cell lines which are comparable to the infamous anti-cancer drug, cisplatin. The cytotoxixity of this complex series increased as the ligands size extended in order of [Ru(bpy)2L]2+ < [Ru(phen)2L]2+ < [Ru(dppz)2L]2+. The interaction of both new complexes [Ru(dppz)2PIP]2+ and [Ru(dppz)2p-HPIP]2+ with CT-DNA were explored by using UV-Vis absorption titration, fluorescence quenching and viscosity measurement. These studies suggest that the two Ru(II) complexes bind to DNA via intercalation, which involves the insertion of ligands in between DNA base pairs. The absorption titration determined that, [Ru(dppz)2p-HPIP]2+ (Kb = 5.0 x 107 M-1) bind strongly to DNA strongly than [Ru(dppz)2PIP]2+ (Kb = 2.5 x 106 M-1). The intramolecular hydrogen bonding in HPIP complex increases the surface area of the intercalating diimines and enhances the DNA binding affinity substantially. 2015-03 Thesis http://psasir.upm.edu.my/id/eprint/64862/ http://psasir.upm.edu.my/id/eprint/64862/1/FS%202015%2029IR.pdf text en public masters Universiti Putra Malaysia
institution	Universiti Putra Malaysia
collection	PSAS Institutional Repository
language	English
topic
spellingShingle	Harun, Siti Norain Synthesis, cytotoxicity and dna binding studies of ruthenium(ii) mixed-polypyridyl complexes
description	A series of ruthenium(II) complexes, including two novel compounds [Ru(dppz)2L]2+ where dppz = dipyrido-[3,2-a:2’,3’-c]phenazine, and L = 2-phenylimidazo[4,5- f][1,10]phenanthroline (PIP) or 2-(4-hydroxyphenyl)imidazo[4,5-f][1,10] phenanthroline (p-HPIP) have been synthesized and characterized. The previously reported complexes [Ru(bpy)2L]2+ and [Ru(phen)2L]2+ were also prepared. All complexes were characterized by elemental analysis, 1H-NMR spectroscopy, ESI-Mass spectroscopy and FT-IR spectroscopy. The photophysical properties were analyzed by UV-Visible spectroscopy and fluorescence spectroscopy. [Ru(dppz)2PIP]2+ and [Ru(dppz)2p-HPIP]2+ displayed ‘molecular light-switch’ effect as they have high emission in acetonitrile but no emission in water. The cytotoxicity of all complexes against cancer cell lines Hela and MCF-7 were investigated through standard MTT assay. [Ru(dppz)2PIP]2+ showed moderate toxicity on both MCF-7 and Hela with IC50 of 37.64 µM and 28.02 µM, respectively. Interestingly, [Ru(dppz)2p-HPIP]2+ exhibited remarkable cytotoxicity results with IC50 of 13.52 µM on Hela and 11.63 µM on MCF- 7 cell lines which are comparable to the infamous anti-cancer drug, cisplatin. The cytotoxixity of this complex series increased as the ligands size extended in order of [Ru(bpy)2L]2+ < [Ru(phen)2L]2+ < [Ru(dppz)2L]2+. The interaction of both new complexes [Ru(dppz)2PIP]2+ and [Ru(dppz)2p-HPIP]2+ with CT-DNA were explored by using UV-Vis absorption titration, fluorescence quenching and viscosity measurement. These studies suggest that the two Ru(II) complexes bind to DNA via intercalation, which involves the insertion of ligands in between DNA base pairs. The absorption titration determined that, [Ru(dppz)2p-HPIP]2+ (Kb = 5.0 x 107 M-1) bind strongly to DNA strongly than [Ru(dppz)2PIP]2+ (Kb = 2.5 x 106 M-1). The intramolecular hydrogen bonding in HPIP complex increases the surface area of the intercalating diimines and enhances the DNA binding affinity substantially.
format	Thesis
qualification_level	Master's degree
author	Harun, Siti Norain
author_facet	Harun, Siti Norain
author_sort	Harun, Siti Norain
title	Synthesis, cytotoxicity and dna binding studies of ruthenium(ii) mixed-polypyridyl complexes
title_short	Synthesis, cytotoxicity and dna binding studies of ruthenium(ii) mixed-polypyridyl complexes
title_full	Synthesis, cytotoxicity and dna binding studies of ruthenium(ii) mixed-polypyridyl complexes
title_fullStr	Synthesis, cytotoxicity and dna binding studies of ruthenium(ii) mixed-polypyridyl complexes
title_full_unstemmed	Synthesis, cytotoxicity and dna binding studies of ruthenium(ii) mixed-polypyridyl complexes
title_sort	synthesis, cytotoxicity and dna binding studies of ruthenium(ii) mixed-polypyridyl complexes
granting_institution	Universiti Putra Malaysia
publishDate	2015
url	http://psasir.upm.edu.my/id/eprint/64862/1/FS%202015%2029IR.pdf
_version_	1747812323758702592

Synthesis, cytotoxicity and dna binding studies of ruthenium(ii) mixed-polypyridyl complexes

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