Targeted photodynamic therapy in visible light using BODIPY-appended copper(II) complexes of a vitamin B-6 Schiff base

Mukherjee, Nandini and Podder, Santosh and Mitra, Koushambi and Majumdar, Shamik and Nandi, Dipankar and Chakravarty, Akhil R (2018) Targeted photodynamic therapy in visible light using BODIPY-appended copper(II) complexes of a vitamin B-6 Schiff base. In: DALTON TRANSACTIONS, 47 (3). pp. 823-835.

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Abstract

Copper(II) complexes Cu(L-1/L-2/L-3)(A)] (1-3), where H(2)A center dot HCl is a vitamin B-6 Schiff base, viz. 3-hydroxy-5-(hydroxymethyl)-4-(((2-hydroxyphenyl) imino) methyl)-2-methylpyridin-1-ium chloride, L-1 and L-2 are 2-(2-pyridyl) benzimidazole based borondipyrromethene (BODIPY) ligands and L-3 is 2-(2-pyridyl) benzimidazole, were prepared, characterized and their visible light-induced anti-cancer activity was studied. Complex 3, characterized by X-ray crystallography, exhibits a distorted square-pyramidal geometry for copper (tau = 0.33). Complexes 1 and 2 showed absorption bands at 500 and 535 nm, respectively, in 20% DMSO/Dulbecco's phosphate buffered saline (DPBS) medium. Complex 1 exhibited emission at similar to 510 nm (lambda(exc) = 480 nm) (Phi(F) = 0.1) in 20% DMSO/DPBS, while the non-emissive diiodo-BODIPY complex 2 is an efficient photosensitizer. The green fluorescent complex 1 enabled us to study its cellular uptake and localization. It showed selective uptake in proliferating cancer cells and significant mitochondrial localization (Pearson's coefficient = 0.7). Complex 2 showed excellent photocytotoxicity (400-700 nm, 10 J cm(-2)) in HeLa, MCF-7 and HepG2 cancer cells with IC50 values within 0.4-0.6 mu M, while remaining less toxic in the dark and in non-cancerous HPL1D cells (photocytotoxic index similar to 50). Complex 2, remarkable in targeting cancer cells over non-cancerous cells, showed photoinduced generation of singlet oxygen, causing apoptotic cell death, thus satisfying the major requirements of targeted photodynamic therapy.

Item Type:	Journal Article
Publication:	DALTON TRANSACTIONS
Publisher:	10.1039/c7dt03976j
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 Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	02 Mar 2018 15:07
Last Modified:	02 Mar 2018 15:07
URI:	http://eprints.iisc.ac.in/id/eprint/58876

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