Planar triazinium cations from vanadyl-mediated ring cyclizations: the thiazole species for efficient nuclear staining and photocytotoxicity

Prasad, Puja and Khan, Imran and Sasmal, Pijus K and Koley, Debasis and Kondaiah, Paturu and Chakravarty, Akhil R (2013) Planar triazinium cations from vanadyl-mediated ring cyclizations: the thiazole species for efficient nuclear staining and photocytotoxicity. In: DALTON TRANSACTIONS, 42 (13). pp. 4436-4449.

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Abstract

Planar triazinium cationic species from vanadyl-assisted cyclization of 1-(2-thiazolylazo)-2-naphthol (H-TAN, 1), 1-(2-pyridylazo)-2-naphthol (H-PAN, 2), 2-(2'-thiazolylazo)-p-cresol (H-TAC, 3) and 6-(2'-thiazolylazo)- resorcinol (H-TAR, 5) were prepared and characterized. A dioxovanadium(V) species VO2(TAR)] (4) was also isolated. Compounds 1, 2 and 4 were structurally characterized. Both 1 and 2 have planar structures. Complex 4 has (VO3N2)-O-V coordination geometry. The cyclised triazinium compound forms a radical species within -0.06 to -0.29 V vs. SCE in DMF-0.1 M tetrabutylammonium perchlorate with a second response due to formation of an anionic species. A confocal microscopic study showed higher nuclear uptake for 1 having a fused thiazole moiety than 2 with a fused pyridine ring. The compounds showed a partial intercalative mode of binding to calf thymus DNA. Compound 1 showed plasmid DNA photo-cleavage activity under argon and photocytotoxicity in HeLa and MCF-7 cells with IC50 values of 15.1 and 3.4 mu M respectively in visible light of 400-700 nm, while being essentially non-toxic in the dark with IC50 values of 90.4 and 21.9 mu M. ATDDFT study was done to rationalize the experimental data.

Item Type:	Journal Article
Publication:	DALTON TRANSACTIONS
Publisher:	ROYAL SOC CHEMISTRY
Additional Information:	Copyright for this article belongs to the ROYAL SOC CHEMISTRY, ENGLAND.
Department/Centre:	Division of Biological Sciences > Molecular Reproduction, Development & Genetics Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	12 Apr 2013 10:36
Last Modified:	12 Apr 2013 10:36
URI:	http://eprints.iisc.ac.in/id/eprint/46407

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