Mitochondria-Targeting Iron(III) Catecholates for Photoactivated Anticancer Activity under Red Light

Basu, Uttara and Pant, Ila and Kondaiah, Paturu and Chakravarty, Akhil R (2016) Mitochondria-Targeting Iron(III) Catecholates for Photoactivated Anticancer Activity under Red Light. In: EUROPEAN JOURNAL OF INORGANIC CHEMISTRY (7). pp. 1002-1012.

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Abstract

Iron(III) catecholates Fe(R-bpa)(R-dopa)Cl] (1, 2) with a triphenylphosphonium (TPP) moiety, where R-bpa is 2-(TPP-N,N-bis((pyridin-2-yl)methyl)ethanamine) chloride (TPPbpa) and R-dopa is 4-{2-(anthracen-9-yl)methylamino]ethyl}benzene-1,2-diol (andopa, 1) or 4-{2-(pyren-1-yl)-methylamino]ethyl}benzene-1,2-diol (pydopa, 2), were synthesized and their photocytotoxicity studied. Complexes 3 and 4 with phenyl-N,N-bis(pyridin-2-yl)methyl]methanamine (phbpa) were used as controls. The catecholate complexes showed an absorption band near 720 nm. The 5e(-) paramagnetic complexes showed a Fe-III/Fe-II irreversible response near -0.45 V and a quasi-reversible catechol/semiquinone couple near 0.5 V versus saturated calomel electrode (SCE) in DMF/0.1 M tetrabutylammonium perchlorate. They showed photocytotoxicity in red/visible light in HeLa, HaCaT, MCF-7, and A549 cells. Complexes 1 and 2 displayed mitochondrial localization, reactive oxygen species (ROS) generation under red light, and apoptotic cell death. Control complexes 3 and 4 exhibited uniform distribution throughout the cell. The complexes showed DNA photocleavage under red light (785 nm), forming hydroxyl radicals as the ROS.

Item Type:	Journal Article
Publication:	EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
Publisher:	WILEY-V C H VERLAG GMBH
Additional Information:	Copy right for this aticle belongs to the WILEY-V C H VERLAG GMBH, POSTFACH 101161, 69451 WEINHEIM, GERMANY
Keywords:	Bioinorganic chemistry; Medicinal chemistry; Anticancer agents; Iron; Mitochondrial localization
Department/Centre:	Division of Biological Sciences > Molecular Reproduction, Development & Genetics Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	23 Apr 2016 06:10
Last Modified:	23 Apr 2016 06:10
URI:	http://eprints.iisc.ac.in/id/eprint/53688

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