Planar triazinium cations from vanadyl-mediated ring cyclizations: the thiazole species for efficient nuclear staining and photocytotoxicity
Prasad, P; Khan, I; Sasmal, PK; Koley, D; Kondaiah, P; Chakravarty, AR
HERO ID
1521068
Reference Type
Journal Article
Year
2013
Language
English
PMID
| HERO ID | 1521068 |
|---|---|
| In Press | No |
| Year | 2013 |
| Title | Planar triazinium cations from vanadyl-mediated ring cyclizations: the thiazole species for efficient nuclear staining and photocytotoxicity |
| Authors | Prasad, P; Khan, I; Sasmal, PK; Koley, D; Kondaiah, P; Chakravarty, AR |
| Journal | Dalton Transactions (Online) |
| Volume | 42 |
| Issue | 13 |
| Page Numbers | 4436-4449 |
| Abstract | Planar triazinium cationic species from vanadyl-assisted cyclization of 1-(2-thiazolylazo)-2-naphthol (H-TAN, ), 1-(2-pyridylazo)-2-naphthol (H-PAN, ), 2-(2'-thiazolylazo)-p-cresol (H-TAC, ) and 6-(2'-thiazolylazo)-resorcinol (H-TAR, ) were prepared and characterized. A dioxovanadium(v) species [VO(TAR)] () was also isolated. Compounds , and were structurally characterized. Both and have planar structures. Complex has VON 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 having a fused thiazole moiety than with a fused pyridine ring. The compounds showed a partial intercalative mode of binding to calf thymus DNA. Compound showed plasmid DNA photo-cleavage activity under argon and photocytotoxicity in HeLa and MCF-7 cells with IC values of 15.1 and 3.4 μM respectively in visible light of 400-700 nm, while being essentially non-toxic in the dark with IC values of 90.4 and 21.9 μM. A TDDFT study was done to rationalize the experimental data. |
| Doi | 10.1039/c2dt32810k |
| Pmid | 23360958 |
| Wosid | WOS:000316294400017 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |