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Mitochondria-localizing BODIPY-copper(II) conjugates for cellular imaging and photo-activated cytotoxicity forming singlet oxygen

Bhattacharyya, Arnab and Jameei, Aida and Garai, Aditya and Saha, Rupak and Karande, Anjali A and Chakravarty, Akhil R (2018) Mitochondria-localizing BODIPY-copper(II) conjugates for cellular imaging and photo-activated cytotoxicity forming singlet oxygen. In: DALTON TRANSACTIONS, 47 (14). pp. 5019-5030.

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Official URL: http://dx.doi.org/ 10.1039/c8dt00255j

Abstract

Copper(ii) acetylacetonates of N,N,N-donor dipicolylamine (dpa) ligands, viz. Cu(L-1)(acac)]ClO4 (1), Cu(L-2)(acac)]ClO4 (2) and Cu(L-3)(acac)]ClO4 (3), where L-1 is benzyldipicolylamine (bzdpa), L-2 and L-3 are non-iodinated and diiodinated BODIPY (borondipyrromethene) ligands and Hacac is acetylacetone, were synthesized and characterized and their photocytotoxicity was studied. The BODIPY complex 2, structurally characterized by X-ray crystallography, has copper(ii) in a distorted square-pyramidal geometry (degree of trigonality, (5) = 0.28). The one-electron paramagnetic and redox active copper(ii) complexes displayed 1:1 electrolytic behaviour in polar organic solvents. The BODIPY complexes 2 and 3 showed respective visible bands at 498 and 539 nm in 5% DMSO-phosphate buffered saline (PBS). Complex 2 displayed an emission band at 511 nm in 5% DMSO-PBS ((ex) = 465 nm) with a fluorescence quantum yield (phi(F)) value of 0.15. Cellular imaging using this complex showed significant mitochondrial localization in HeLa and MCF-7 cancer cells. Complex 3 with a diiodo-BODIPY moiety was non-emissive (phi(F) = 0.01) but acted as an efficient photosensitizer with a singlet oxygen quantum yield value of 0.59 (phi). Complex 3 showed a remarkable PDT effect with apoptotic cell death due to singlet oxygen giving IC50 values within 0.04-0.06 M in HeLa and MCF-7 cells using visible light (400-700 nm), while being less toxic in the dark.

Item Type: Journal Article
Additional Information: Copy right for this article belong to ROYAL SOC CHEMISTRY, THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
Department/Centre: Division of Biological Sciences > Biochemistry
Division of Chemical Sciences > Inorganic & Physical Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 04 May 2018 18:49
Last Modified: 04 May 2018 18:49
URI: http://eprints.iisc.ac.in/id/eprint/59714

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