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Voltammetric detection and analysis of the behavior of diethylstilbestrol oxidation products
Author(s) -
Séquaris JeanMarie,
Fritz Joan
Publication year - 1992
Publication title -
electroanalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.574
H-Index - 128
eISSN - 1521-4109
pISSN - 1040-0397
DOI - 10.1002/elan.1140040121
Subject(s) - chemistry , tautomer , cyclic voltammetry , dimethylformamide , reactivity (psychology) , quinone , kinetics , voltammetry , semiquinone , diethylstilbestrol , medicinal chemistry , photochemistry , stereochemistry , organic chemistry , electrochemistry , electrode , medicine , physics , alternative medicine , pathology , quantum mechanics , solvent , biochemistry , hormone
Peroxidase‐mediated oxidation of diethylstibestrol (DES), a synthetic estrogen, has been proposed as a pathway in DES‐induced carcinogenicity. However, the transient nature of the DES oxidation product, DES‐quinone (DES‐Q), requires a rapid method such as cyclic voltammetry to study its stability and reactivity. Thus, the irreversible tautomerization of DES‐Q into dienstrol form (Z, Z‐DIES) is described by a two step mechanism. Tautomerization kinetics are studied as a function of pH and temperature. A significant descrease of half‐life for DES‐Q is observed in the presence of the glutathione thiolate form. Furthermore, voltammetric investigations were performed in dimethylformamide to detect the semiquinone radical of DES‐Q, a suspected genotoxic product.
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