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


Autoria(s): Prasad, Puja; Khan, Imran; Sasmal, Pijus K; Koley, Debasis; Kondaiah, Paturu; Chakravarty, Akhil R
Data(s)

2013

Resumo

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.

Formato

application/pdf

Identificador

http://eprints.iisc.ernet.in/46407/1/dal_tra_42_13_4436_2013.pdf

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.

Publicador

ROYAL SOC CHEMISTRY

Relação

http://dx.doi.org/10.1039/c2dt32810k

http://eprints.iisc.ernet.in/46407/

Palavras-Chave #Molecular Reproduction, Development & Genetics (formed by the merger of DBGL and CRBME) #Inorganic & Physical Chemistry
Tipo

Journal Article

PeerReviewed