Azide derivatized anticancer agents of vitamin K-3: X-ray structural, DSC, resonance spectral and API studies

TitleAzide derivatized anticancer agents of vitamin K-3: X-ray structural, DSC, resonance spectral and API studies
Publication TypeJournal Article
Year of Publication2011
AuthorsBadave, KD, Patil, Y, Gonnade, RG, Srinivas, D, Dasgupta, R, Khan, AA, Rane, S
JournalJournal of Molecular Structure
Volume1006
Issue1-3
Pagination288-296
Date PublishedDEC
ISSN0022-2860
KeywordsAnticancer agents, API (Active Pharmaceutical Ingredients), Electronic isomers, RAHB (resonance assisted H-bonding), Vitamin K-3
Abstract

Compound 1 [1-imino (acetyl hydrazino)-Vitamin K-3], displays valence tautomerically related electronic isomers as Form land Form II. Form I exhibits 2D packing fragment with 1D ribbon chains of N-H center dot center dot center dot O hydrogen bonds and shows EPR silent features. While Form II is EPR active and exhibits biradical nature with double quantum transitions at g = 2.0040. H-1 NMR of compound 2, [1-imino (hydrazino carboxylate)-Vitamin K-3] and Form II exhibit pi delocalization via resonance assisted H-bonding [RAHB] effect compared to Form I. Molecular interactions in Form I and II are visualized by DSC. The electronic structures of compounds 1 and 2 have been correlated to their API values by measuring anticancer activities, mitochondrial potentials and DNA shearing patterns. Form II and compound 2 indicate mitochondria mediated apoptosis (similar to 75% cell death) while Form I causes 35% cell death. (C) 2011 Elsevier B.V. All rights reserved.

DOI10.1016/j.molstruc.2011.09.022
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

1.634

Divison category: 
Catalysis and Inorganic Chemistry
Center for Material Characterization (CMC)