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Curcumin ``Drug'' Stabilized in Oxidovanadium(IV)-BODIPY Conjugates for Mitochondria-Targeted Photocytotoxicity

Bhattacharyya, Utso and Kumar, Brijesh and Garai, Aditya and Bhattacharyya, Arnab and Kumar, Arun and Banerjee, Samya and Kondaiah, Paturu and Chakravarty, Akhil R (2017) Curcumin ``Drug'' Stabilized in Oxidovanadium(IV)-BODIPY Conjugates for Mitochondria-Targeted Photocytotoxicity. In: INORGANIC CHEMISTRY, 56 (20). pp. 12457-12468.

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Official URL: http://doi.org/10.1021/acs.inorgchem.7b01924


Ternary oxidovanadium(IV) complexes of curcumin (Hcur), dipicolylamine (dpa) base, and its derivatives having pendant noniodinated and di-iodinated boron-dipyrromethene (BODIPY) moiety (L-1 and L-2 respectively), namely, VO(dpa)(cur)]ClO4 (1), VO(L-1)(cur)] ClO4 (2), and VO(L-2)(cur)]ClO4 (3) and their chloride salts (1a-3a) were prepared, characterized, and studied for anticancer activity. The chloride salts were used for biological studies due to their aqueous solubility. Complex 1 was structurally characterized by single-crystal X-ray crystallography. The complex has a VO2+ moiety bound to dpa ligand showing N,N,N-coordination in a facial mode, and curcumin is bound in its mono-anionic enolic form. The V-O(cur) distances are 1.950(18) and 1.977(16) angstrom, while the V-N bond lengths are 2.090(2), 2.130(2), and 2.290(2) angstrom. The bond trans to V=O is long due to trans effect. The complexes are stable in a solution phase over a long period of time of 48 h without showing any apparent degradation of the curcumin ligand. The diiodo-BODIPY ligand (L-2) or Hcur alone showed limited solution stability in dark. The emissive BODIPY (L-1) containing complex 2a showed preferential mitochondrial localization in MCF-7 cells in cellular imaging experiments. The cytotoxicity of the complexes was studied by MTT assay. The BODIPY complex 3a showed excellent photodynamic therapy effect in visible light (400-700 nm) giving IC50 values of 2-6 mu M in HeLa and MCF-7 cancer cells, while being less toxic in dark (similar to 100 mu M). The cell death was apoptotic in nature involving reactive oxygen species (ROS). Mechanistic data from pUC19 DNA photocleavage studies revealed photogenerated ROS as primarily O-1(2) from the BODIPY moiety and center dot OH radicals from the curcumin ligand.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited: 11 Nov 2017 07:10
Last Modified: 11 Nov 2017 07:10
URI: http://eprints.iisc.ac.in/id/eprint/58200

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