Medical College of Wisconsin
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Characterization of free radicals produced during oxidation of etoposide (VP-16) and its catechol and quinone derivatives. An ESR Study. Biochemistry 1989 May 30;28(11):4839-46

Date

05/30/1989

Pubmed ID

2548593

DOI

10.1021/bi00437a048

Scopus ID

2-s2.0-0024372292 (requires institutional sign-in at Scopus site)   73 Citations

Abstract

Spectroscopic evidence for the radical-mediated metabolism of VP-16, VP-16 catechol, and VP-16 quinone during enzymatic oxidation and autoxidation has been obtained. Autoxidation of the catechol yields the primary semiquinone together with the primary molecular product VP-16 quinone, which subsequently undergoes hydrolytic oxidation to form secondary quinones and semiquinones. Both primary and secondary phenoxyl radicals were detected during peroxidatic oxidation of VP-16. Neither the primary nor the secondary radicals react with DNA at a detectable rate. Evidence for the production of hydroxyl radical during iron-catalyzed oxidation of VP-16 catechol was obtained. These free radical reactions may have implications for the mechanism of antitumor action of VP-16.

Author List

Kalyanaraman B, Nemec J, Sinha BK

Author

Balaraman Kalyanaraman PhD Professor in the Biophysics department at Medical College of Wisconsin




MESH terms used to index this publication - Major topics in bold

Catechols
Computer Simulation
DNA
DNA Damage
Electron Spin Resonance Spectroscopy
Etoposide
Free Radicals
Hydroxides
Mathematics
Oxidation-Reduction
Phenols
Quinones