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Molecular basis of the antitumor activities of 2-crotonyloxymethyl-2-cycloalkenones. | LitMetric
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Molecular basis of the antitumor activities of 2-crotonyloxymethyl-2-cycloalkenones.

Erin Joseph Julie L Eiseman Diana S Hamilton Haibo Wang Heekyung Tak Zhebo Ding Bruce Ganem Donald J Creighton

J Med Chem

Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland 21250, USA.

Published: January 2003

The antitumor activity of 2-crotonyloxymethyl-2-cyclohexenone (COMC-6) is not the result of the GSH conjugate (GSMC-6) formed inside tumor cells, as the diethyl ester prodrug form of GSMC-6 displays little antitumor activity with B16 melanotic melanoma in vitro (IC(50) > 460 microM) versus COMC-6 (IC(50) 0.041 microM) and its five- and seven-membered ring homologues. Antitumor activity probably results from a reactive intermediate that forms during conjugation of the COMCs with intracellular GSH.

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http://dx.doi.org/10.1021/jm0203027DOI Listing

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