DNA Photocleavage and Cytotoxic Properties of Ferrocene Conjugates

Maity, Basudev and Chakravarthi, Balabhadrapatruni VSK and Roy, Mithun and Karande, Anjali A and Chakravarty, Akhil R (2011) DNA Photocleavage and Cytotoxic Properties of Ferrocene Conjugates. In: European Journal of Inorganic Chemistry (9). pp. 1379-1386.

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Abstract

Ferrocenyl conjugates 2-ferrocenylimidazophenanthroline (1) and 2-ferrocenylimidazophenanthrene (2) were prepared, characterized, and their photoinduced DNA cleavage and photocytotoxic activity were studied. 2-Phenylimidazophenanthroline (3) was used as a control species. Compound 2 was characterized by X-ray crystallography. The interaction of the compounds with double-stranded calf thymus DNA (CT DNA) was studied. The compounds show good binding affinity to CT DNA with K-b values of approximately 10(5) M-1. Thermal denaturation data suggest the groove binding nature of the compounds. The redox-active compounds show poor chemical nuclease activity in the presence of hydrogen peroxide and glutathione (GSH). Compound 1 exhibits significant DNA photocleavage activity in visible light of 476 and 532 nm. Compound 3 shows only moderate DNA cleavage activity. The positive effect of the ferrocenyl moiety is demonstrated by the DNA photocleavage data. Mechanistic investigations reveal the formation of superoxide as well as hydroxyl radicals as the active species. The photocytotoxicity of the compounds in HeLa cells was studied upon irradiation with visible light (400-700 nm). Compound 1 shows efficient photocytotoxic activity with an IC50 value of 13 mu M, while compounds 2 and 3 are less active with IC50 values of > 50 and 22 mu M, respectively.

Item Type:	Journal Article
Publication:	European Journal of Inorganic Chemistry
Publisher:	John Wiley and Sons
Additional Information:	Copyright of this article belongs to John Wiley and Sons.
Keywords:	Metallocenes; Iron; DNA cleavage; Cytotoxicity; Photodynamic therapy
Department/Centre:	Division of Biological Sciences > Biochemistry Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	05 Apr 2011 07:29
Last Modified:	05 Apr 2011 07:29
URI:	http://eprints.iisc.ac.in/id/eprint/36600

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