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- W230104071 abstract "Glutathione (GSH) S-transferase catalyzes the reaction of the carcinogen 1,2-dibromoethane (DBE) with DNA, resulting in the formation of a major DNA adduct which can be released by thermal hydrolysis at neutral pH and purified by octadecylsilyl- and propylamino high performance liquid chromatography. This adduct was also the only major liver and kidney DNA adduct isolated from rats treated with (1,2-/sup 14/C)-DBE. Administration of 1,2-dichloroethane to rats also led to the production of this and other DNA adducts. The DNA adduct was assigned the structure S-(2-(N'-guanyl)ethyl)GSH as determined by positive and negative ion mass spectrometry and two-dimensional NMR correlated spectroscopy (COSY). Consistently, the chromatographic characteristics of the adduct could be altered upon treatment with ..gamma..-glutamic transpeptidase or pronase. No evidence for in vitro or in vivo guanyl imidazole ring opening was observed under these experimental conditions. Additionally, S-(2-(N/sup 7/-guanyl)ethyl)GSH was found to be stable to further reaction with DNA to generate new DNA adducts. The structure of the isolated adduct is consistent with a proposed bioactivation pathway of DBE which involves enzyme catalyzed conjugation of DBE with GSH followed by attack of the N/sup 7/-position of DNA guanine residues to generate this major adduct. The chemical stability of the adduct suggestsmore » that it may be important to the carcinogenicity of this compound.« less" @default.
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- W230104071 date "1986-05-01" @default.
- W230104071 modified "2023-09-28" @default.
- W230104071 title "Structural and chemical characterization of S-(2-(N/sup 7/-guanyl)-ethyl)glutathione, the major DNA adduct formed from 1,2-dibromoethane" @default.
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