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BODIPY appended copper(II) complexes for cellular imaging and singlet oxygen mediated anticancer activity in visible light

Bhattacharyya, Arnab and Dixit, Akanksha and Banerjee, Samya and Roy, Bijan and Kumar, Arun and Karande, Anjali A and Chakravarty, Akhil R (2016) BODIPY appended copper(II) complexes for cellular imaging and singlet oxygen mediated anticancer activity in visible light. In: RSC ADVANCES, 6 (106). pp. 104474-104482.

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Official URL: http://dx.doi.org/10.1039/c6ra23118g

Abstract

Copper(II) complexes of N,N,N-donor dipicolylamine ligands, viz. Cu(L-1)Cl-2] (1), Cu(L-2)Cl-2] (2) and Cu(L-3) Cl-2] (3) with L-2 and L-3 having BODIPY (borondipyrromethene) moieties were synthesized, characterized and their photocytotoxicity studied. Complex 1 was structurally characterized by X-ray crystallography. It has copper(II) in a distorted square-pyramidal geometry (tau = 0.11) with two chloride ligands in axial-equatorial cis-disposition. The one-electron paramagnetic and redox active complexes are non-electrolytic in DMF. They behave as 1 : 1 and 1 : 2 electrolytes in 1 : 1 and 1 : 9 (v/v) DMF-H2O. The BODIPY complexes 2 and 3 show respective visible bands at 501 nm and 535 nm in DMF. Complex 2 displays an emission band at 515 nm in DMF (lambda(ex) = 465 nm) with a quantum yield (Phi(F)) value of 0.14. This complex, as a fluorogenic probe for cellular imaging, shows cytosolic localisation of the complex in HeLa and MCF-7 cancer cells. Complex 3 having a diiodo BODIPY unit in L-3 is non-emissive but acts as an efficient photosensitizer showing a significant PDT effect with apoptotic cell death forming singlet oxygen as ROS (phi(Delta) - 0.53) and giving respective IC50 values of 0.15 +/- 0.02 and 0.17 +/- 0.03 mu M in HeLa and MCF-7 cancer cells in visible light of 400-700 nm, while being less toxic in the dark.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the 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: 30 Dec 2016 07:21
Last Modified: 30 Dec 2016 07:21
URI: http://eprints.iisc.ac.in/id/eprint/55658

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