Matches in SemOpenAlex for { <https://semopenalex.org/work/W1982191774> ?p ?o ?g. }
Showing items 1 to 86 of
86
with 100 items per page.
- W1982191774 endingPage "924" @default.
- W1982191774 startingPage "917" @default.
- W1982191774 abstract "Oxidation of catechol estrogens (CE) leads to the reactive electrophilic CE quinones. Reaction of CE-3,4-quinones with DNA has been implicated in tumor initiation. One pathway to prevent this reaction is conjugation of CE quinones with glutathione (GSH). Four CE, 4-hydroxy estrone (4-OHE1), 4-hydroxyestradiol (4-OHE2), 2-OHE1, and 2-OHE2, were conjugated with GSH after oxidation catalyzed by horseradish peroxidase (HRP), lactoperoxidase (LP), or rat liver microsomal cytochrome P450. This reaction is a free-radical chain autoxidation that produces very high yields of products. Six mono-GSH conjugates, 4-OHE1(E2)-2-SG, 2-OHE1(E2)-1-SG, and 2-OHE1(E2)-4-SG, and four di-GSH conjugates, 4-OHE1(E2)-1,2-bisSG and 2-OHE1(E2)-1,4-bisSG, were identified and quantified. These di-GSH conjugates were also obtained quantitatively from oxidation of mono-GSH conjugates by the same enzymes. HRP and LP gave very similar product profiles. Phenobarbital- and 3-methylcholanthrene-induced microsomes with either NADPH or cumene hydroperoxide as cofactor oxidized 4-OHE2 to form similar amounts of GSH conjugates. Enzymatic oxidation of 2-OHE1(E2) in the presence of GSH produced more 2-OHE1(E2)-4-SG than the 1-isomer. This contrasts with the direct reaction of E1(E2)-2,3-Q and GSH, in which the 1-isomer is formed more abundantly than the 4-isomer (Cao, K., Devanesan, P. D., Ramanathan, R., Gross, M. L., Rogan, E. G., and Cavalieri, E. L. (1998) Chem. Res. Toxicol. 11, 909−916). Competitive enzymatic oxidation of equimolar 4-OHE2 and 2-OHE2 in the presence of an equimolar amount of GSH yielded more 2-OHE2 conjugates than 4-OHE2 conjugates, despite E2-3,4-Q being more reactive with GSH than E2-2,3-Q. These results suggest that 2-OHE2 is a better substrate than 4-OHE2 in the catalytic oxidation to quinones, despite the greater reactivity of E2-3,4-Q, compared to E2-2,3-Q, with GSH." @default.
- W1982191774 created "2016-06-24" @default.
- W1982191774 creator A5031404252 @default.
- W1982191774 creator A5031479644 @default.
- W1982191774 creator A5047028112 @default.
- W1982191774 creator A5058789108 @default.
- W1982191774 creator A5059143128 @default.
- W1982191774 creator A5067482412 @default.
- W1982191774 date "1998-07-21" @default.
- W1982191774 modified "2023-09-27" @default.
- W1982191774 title "Covalent Binding of Catechol Estrogens to Glutathione Catalyzed by Horseradish Peroxidase, Lactoperoxidase, or Rat Liver Microsomes" @default.
- W1982191774 cites W2041258563 @default.
- W1982191774 cites W2065725392 @default.
- W1982191774 cites W2993939875 @default.
- W1982191774 doi "https://doi.org/10.1021/tx9702300" @default.
- W1982191774 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/9705754" @default.
- W1982191774 hasPublicationYear "1998" @default.
- W1982191774 type Work @default.
- W1982191774 sameAs 1982191774 @default.
- W1982191774 citedByCount "24" @default.
- W1982191774 countsByYear W19821917742012 @default.
- W1982191774 countsByYear W19821917742013 @default.
- W1982191774 countsByYear W19821917742014 @default.
- W1982191774 countsByYear W19821917742016 @default.
- W1982191774 countsByYear W19821917742018 @default.
- W1982191774 crossrefType "journal-article" @default.
- W1982191774 hasAuthorship W1982191774A5031404252 @default.
- W1982191774 hasAuthorship W1982191774A5031479644 @default.
- W1982191774 hasAuthorship W1982191774A5047028112 @default.
- W1982191774 hasAuthorship W1982191774A5058789108 @default.
- W1982191774 hasAuthorship W1982191774A5059143128 @default.
- W1982191774 hasAuthorship W1982191774A5067482412 @default.
- W1982191774 hasConcept C155647269 @default.
- W1982191774 hasConcept C161790260 @default.
- W1982191774 hasConcept C162008176 @default.
- W1982191774 hasConcept C181199279 @default.
- W1982191774 hasConcept C185592680 @default.
- W1982191774 hasConcept C201956729 @default.
- W1982191774 hasConcept C2777676563 @default.
- W1982191774 hasConcept C2777713698 @default.
- W1982191774 hasConcept C2778113725 @default.
- W1982191774 hasConcept C2778656385 @default.
- W1982191774 hasConcept C37329643 @default.
- W1982191774 hasConcept C538909803 @default.
- W1982191774 hasConcept C55493867 @default.
- W1982191774 hasConcept C71240020 @default.
- W1982191774 hasConcept C71315377 @default.
- W1982191774 hasConcept C87644729 @default.
- W1982191774 hasConceptScore W1982191774C155647269 @default.
- W1982191774 hasConceptScore W1982191774C161790260 @default.
- W1982191774 hasConceptScore W1982191774C162008176 @default.
- W1982191774 hasConceptScore W1982191774C181199279 @default.
- W1982191774 hasConceptScore W1982191774C185592680 @default.
- W1982191774 hasConceptScore W1982191774C201956729 @default.
- W1982191774 hasConceptScore W1982191774C2777676563 @default.
- W1982191774 hasConceptScore W1982191774C2777713698 @default.
- W1982191774 hasConceptScore W1982191774C2778113725 @default.
- W1982191774 hasConceptScore W1982191774C2778656385 @default.
- W1982191774 hasConceptScore W1982191774C37329643 @default.
- W1982191774 hasConceptScore W1982191774C538909803 @default.
- W1982191774 hasConceptScore W1982191774C55493867 @default.
- W1982191774 hasConceptScore W1982191774C71240020 @default.
- W1982191774 hasConceptScore W1982191774C71315377 @default.
- W1982191774 hasConceptScore W1982191774C87644729 @default.
- W1982191774 hasIssue "8" @default.
- W1982191774 hasLocation W19821917741 @default.
- W1982191774 hasLocation W19821917742 @default.
- W1982191774 hasOpenAccess W1982191774 @default.
- W1982191774 hasPrimaryLocation W19821917741 @default.
- W1982191774 hasRelatedWork W1968218338 @default.
- W1982191774 hasRelatedWork W1982191774 @default.
- W1982191774 hasRelatedWork W2011572719 @default.
- W1982191774 hasRelatedWork W2035035944 @default.
- W1982191774 hasRelatedWork W2060591200 @default.
- W1982191774 hasRelatedWork W2062413910 @default.
- W1982191774 hasRelatedWork W2316444864 @default.
- W1982191774 hasRelatedWork W2345250762 @default.
- W1982191774 hasRelatedWork W2153125770 @default.
- W1982191774 hasRelatedWork W3149879979 @default.
- W1982191774 hasVolume "11" @default.
- W1982191774 isParatext "false" @default.
- W1982191774 isRetracted "false" @default.
- W1982191774 magId "1982191774" @default.
- W1982191774 workType "article" @default.