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Organic & Biomolecular Chemistry Vol - 8 Issue - 6

Organic & Biomolecular Chemistry Vol - 8 Issue - 5

Organic & Biomolecular Chemistry Vol - 8 Issue - 4

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Organic & Biomolecular Chemistry Vol -7

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Cyclization kinetics and biological evaluation of an anticancer 1,2-dialkynylimidazole

Content Provider	Royal Society of Chemistry (RSC)
Author	Gonzales, Cristina Kerwin, Sean M. Li, Jing David, Wendi M. Laroche, Christophe
Copyright Year	2010
Abstract	1,2-Dialkynylimidazoles have been reported to undergo thermal cyclization/rearrangement to diradical and carbene intermediates. Optimization of the synthesis of the 1,2-dialkynylimidazole 3 has provided sufficient material for kinetic and biological studies. The 1,2-dialkynylimidazole 3 is cytotoxic against a wide range of cancer cells and induces apoptosis in A549 cells. Experimentally-determined kinetics of the thermolysis of 3 (Ea = 30.0 kcal mol−1) are in excellent agreement with DFT calculations of the cyclization/rearrangement to diradical and cyclopentapyrazine carbene intermediates (Ea = 29.7 kcal mol−1). Commensurate with the relatively high barrier for cyclization of 3, no evidence for cleavage of supercoiled DNA under physiological conditions was found; however, under aqueous conditions at 70 °C 3 formed a covalent adduct with a model peptide. These studies indicate that if cyclization of 3 is involved in its anticancer activity, the cyclization must be facilitated, perhaps through initial protein binding, which could lead to covalent protein modification.
Starting Page	1535
Ending Page	1539
Page Count	5
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	8
Issue Number	7
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b925261d
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Diradical Carbene Thermal decomposition DNA Covalent bond Cytotoxicity Peptide Adduct Protein Cancer Apoptosis
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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