期刊
JOURNAL OF INORGANIC BIOCHEMISTRY
卷 202, 期 -, 页码 -出版社
ELSEVIER SCIENCE INC
DOI: 10.1016/j.jinorgbio.2019.110817
关键词
Vanadium; Bioinorganic chemistry; DNA crosslink; Photodynamic therapy; Crystal structure
资金
- Department of Science and Technology, Government of India [SR/S5/MBD-02/2007, EMR/2015/000742]
- J.C. Bose national fellowship
- Indian Institute of Science (IISc.), Bangalore
- CSIR
- University Grants Commission (UGC), New Delhi
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)-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-10-yl)benzyl)-1-(pyridin-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.
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