Journal
NEW JOURNAL OF CHEMISTRY
Volume 38, Issue 1, Pages 277-284Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3nj00783a
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Funding
- UGC
- University Grants Commission, New Delhi [F34-370/2008(SR)]
- DST
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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.
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