%0 Journal Article %J New Journal of Chemistry %D 2014 %T Cu(II) conjugation along the transformation of a vitamin K-3 derivative to a dinaphthoquinone methide radical %A Badave, Kirti D. %A Patil, Shalaka S. %A Khan, Ayesha A. %A Srinivas, Darbha %A Butcher, Raymond J. %A Gonnade, Rajesh G. %A Puranik, Vedavati G. %A Pinjari, Rahul V. %A Gejji, Shridhar P. %A Rane, Sandhya Y. %X

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.

%B New Journal of Chemistry %I ROYAL SOC CHEMISTRY %C THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND %V 38 %P 277-284 %8 JAN %G eng %N 1 %3

Foreign

%4

3.277

%R 10.1039/c3nj00783a