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An electron spin resonance study of free radicals from catechol estrogens. Fed Proc 1986 Sep;45(10):2477-84

Date

09/01/1986

Pubmed ID

3017766

Scopus ID

2-s2.0-0022460299 (requires institutional sign-in at Scopus site)   19 Citations

Abstract

Electron spin resonance spectroscopy has been used to demonstrate production of semiquinone free radicals from the oxidation of the catechol estrogens 2- and 4-hydroxyestradiol and 2,6- and 4,6-dihydroxyestradiol. Radicals were generated by horseradish peroxidase/H2O2 or tyrosinase/O2, or by autoxidation, and were detected as their complexes with spin-stabilizing metal ions (Zn2+ and/or Mg2+). Radical production occurs via one- or two-electron oxidation of catechol estrogens, depending on the type of activating system. Autoxidation of catechol estrogens produces superoxide and H2O2 at physiological pH values. The present results also indicate a difference in the reactivity of quinones derived from 2- and 4-hydroxyestradiol. The toxicological significance of these reactions is discussed.

Author List

Kalyanaraman B, Hintz P, Sealy RC

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

Animals
Benzoquinones
Chemical Phenomena
Chemistry
Cytochrome P-450 Enzyme System
Electron Spin Resonance Spectroscopy
Estradiol
Estrogens, Catechol
Female
Free Radicals
Horseradish Peroxidase
Hydrogen Peroxide
Isoenzymes
Magnesium
Models, Biological
Monophenol Monooxygenase
Oxidation-Reduction
Oxygen
Peroxidase
Peroxidases
Quinones
Uterus
Zinc