Cu(II) conjugation along the transformation of a vitamin K-3 derivative to a dinaphthoquinone methide radical

TitleCu(II) conjugation along the transformation of a vitamin K-3 derivative to a dinaphthoquinone methide radical
Publication TypeJournal Article
Year of Publication2014
AuthorsBadave, KD, Patil, SS, Khan, AA, Srinivas, D, Butcher, RJ, Gonnade, RG, Puranik, VG, Pinjari, RV, Gejji, SP, Rane, SY
JournalNew Journal of Chemistry
Volume38
Issue1
Pagination277-284
Date PublishedJAN
ISSN1144-0546
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.

DOI10.1039/c3nj00783a
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.277

Divison category: 
Physical and Materials Chemistry