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Crystal structure, DNA crosslinking and photo-induced cytotoxicity of oxovanadium(IV) conjugates of boron-dipyrromethene

Kumar, Arun and Dixit, Akanksha and Sahoo, Somarupa and Banerjee, Samya and Bhattacharyya, Arnab and Garai, Aditya and Karande, Anjali A and Chakravarty, Akhil R (2020) Crystal structure, DNA crosslinking and photo-induced cytotoxicity of oxovanadium(IV) conjugates of boron-dipyrromethene. In: JOURNAL OF INORGANIC BIOCHEMISTRY, 202 .

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Official URL: https:/dx.doi.org/10.1016/j.jinorgbio.2019.110817

Abstract

Cis-dichloro-oxovanadium(IV) complexes VO(L-1/L-2)Cl-2], where L-1 is N-(4-(5,5-difluoro-1,3,7,9-tetramethyl-5H-4(sic)(4),5(sic)(4)-dipyrrolo 1, 2-c:2',1'-f] 1,3, 2]diazaborinin-10-yl)benzyl)-1-(pyridin-2-yl)-N-(pyridin-2-ylmethyl) methanamine in 1 and L-2 is N-(4-(5,5-difluoro-2,8-dliodo-1,3,7,9-tetramethyl-5H-4(sic)(4),5(sic)(4) -dipyrrolo1,2-c:2',1'-f]1,3,2]diazaborinin-10-yl)benzyl)-1-(pyridi n-2-yl)-N-(pyridin-2-ylmethyl)methanamine in 2) having 4,4-di-fluoro-4-bora-3a,4a-diaza-s-indacene as boron-dipyrromethene (BODIPY) appended dipicolylamine bases were prepared, characterized and their photocytotoxicity studied. X-ray crystal structure of 1 showed distorted octahedral geometry with a (VON3Cl2)-O-IV core having Cl-V-Cl angle of 91.93(4)degrees. The complexes showed variable solution conductivity properties. They were non-electrolytes in dry DMF at 25 degrees C but showed 1:1 electrolytic behavior in an aqueous medium due to dissociation of one chloride ligand as evidenced from the mass spectral study. Complexes 1 and 2 showed absorption bands at 500 and 535 nm, respectively. The calf thymus DNA melting study revealed their interaction through DNA crosslinking on exposure to light which was further confirmed from the alkaline agarose gel electrophoresis using plasmid supercoiled pUC19 DNA. Complex 2 showed disruption of the mitochondrial membrane potential in the JC-1 (1,1',3,3'-tetraethyl-5,5',6,6'-tetrachloroimidacarbocyanine iodide) assay. The complexes were photocytotoxic in visible light (400-700 nm, power: 10 J cm(-2)) in cervical cancer HeLa and breast cancer MCF-7 cells. Complex 2 having a photoactive diiodo-boron-dipyrromethene moiety gave a singlet oxygen quantum yield (Phi(Delta)) value of similar to 0.6. It showed singlet oxygen mediated apoptotic photodynamic therapy activity with remarkably low IC50 (half maximal inhibitory concentration) value of similar to 0.15 mu M. The cis-disposition of chlorides gave a cis-divacant 4-coordinate intermediate structure from the density functional theory (DFT) study thus mimicking the DNA crosslinking property of cisplatin.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to ELSEVIER SCIENCE INC, STE 800, 230 PARK AVE, NEW YORK, NY 10169 USA
Keywords: Vanadium; Bioinorganic chemistry; DNA crosslink; Photodynamic therapy; Crystal structure
Department/Centre: Division of Biological Sciences > Biochemistry
Division of Chemical Sciences > Inorganic & Physical Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 10 Jan 2020 07:36
Last Modified: 10 Jan 2020 07:36
URI: http://eprints.iisc.ac.in/id/eprint/64282

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