Cu(II) conjugation along the transformation of a vitamin K3 derivative to a dinaphthoquinone methide radical

被引：1

作者：

Badave, Kirti D. ^{[1
]}

Patil, Shalaka S. ^{[2
]}

Khan, Ayesha A. ^{[2
]}

Srinivas, Darbha ^{[3
]}

Butcher, Raymond J. ^{[4
]}

Gonnade, Rajesh G. ^{[5
]}

Puranik, Vedavati G. ^{[5
]}

Pinjari, Rahul V. ^{[1
]}

Gejji, Shridhar P. ^{[1
]}

Rane, Sandhya Y. ^{[1
]}

机构：

[1] Univ Pune, Dept Chem, Pune 411007, Maharashtra, India

[2] Univ Pune, Inst Bioinformat & Biotechnol, Pune 411007, Maharashtra, India

[3] Natl Chem Lab, Catalysis Div, Pune 411008, Maharashtra, India

[4] Howard Univ, Dept Chem, Washington, DC 20059 USA

[5] Natl Chem Lab, Ctr Mat Characterizat, Pune 411008, Maharashtra, India

来源：

NEW JOURNAL OF CHEMISTRY | 2014年 / 38卷 / 01期

关键词：

QUINONE METHIDE; HYBRID DRUGS; POLYMERIZATION; BIOACTIVATION; ACTIVATION; REACTIVITY; COMPLEXES; OXIDATION; LIGANDS; ASPIRIN;

D O I：

10.1039/c3nj00783a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：277 / 284

页数：8

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