Cu(II) conjugation along the transformation of a vitamin K-3 derivative to a dinaphthoquinone methide radical
| Title | Cu(II) conjugation along the transformation of a vitamin K-3 derivative to a dinaphthoquinone methide radical |
| Publication Type | Journal Article |
| Year of Publication | 2014 |
| Authors | Badave, KD, Patil, SS, Khan, AA, Srinivas, D, Butcher, RJ, Gonnade, RG, Puranik, VG, Pinjari, RV, Gejji, SP, Rane, SY |
| Journal | New Journal of Chemistry |
| Volume | 38 |
| Issue | 1 |
| Pagination | 277-284 |
| Date Published | JAN |
| ISSN | 1144-0546 |
| Abstract | 1,1'-Methide-bi-vitamin K-3 (B) has been isolated as a dinaphthoquinone methide radical (DNQM) by the transformation of 1-imino(acetylhydrazino)-vitamin K-3 (A). The transformation follows a biomimetic activation pathway mediated via Cu(II) ion catalyzed oxidative coupling. Single crystal X-ray and electron spin resonance (ESR) experiments combined with density functional calculations elucidate the ``resonance structure'' of the DNQM radical (B). Fluorescence investigations reveal that DNQM facilitates interaction with the cysteine residue. As compared to the parent substrate, B shows a depletion in the level of GSH, triggering apoptosis in HeLa cells. |
| DOI | 10.1039/c3nj00783a |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.277 |
Divison category:
Physical and Materials Chemistry