FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W1995819466> ?p ?o ?g. }

• W1995819466 endingPage "275" @default.
• W1995819466 startingPage "259" @default.
• W1995819466 abstract "The microsomal oxidation of 1,2-[14C]- and 1,4-[14C]dichlorobenzene (DICB) was investigated with special attention for possible differences in biotransformation that might contribute to the isomer-specific hepatotoxicity. Major metabolites of both isomers were dichlorophenols (2,5-DICP for 1,4-DICB and 2,3- and 3,4-DICP for 1,2-DICB, respectively) and dichlorohydroquinones. The formation of polar dihydrodiols appeared to be a major route for 1,2-DICB but not 1,4-DICB. Both the hepatotoxic 1,2-DICB and the non-hepatotoxic 1,4-DICB were oxidized to metabolites that covalently interacted with protein and only to a small extent with DNA. Protein binding could be inhibited by the addition of the reducing agent ascorbic acid with a concomitant increase in the formation of hydroquinones and catechols, indicating the involvement of reactive benzoquinone metabolites in protein binding. However, in the presence of ascorbic acid, a substantial amount of protein-bound metabolites of 1,2-DICB was still observed, in contrast to 1,4-DICB where binding was nearly completely inhibited. This latter effect was ascribed to the direct formation of reactive benzoquinone metabolites in a single P450-mediated oxidation of para-substituted dichlorophenols (such as 3,4-DICP) in the case of 1,2-DICB. In contrast, the major phenol isomer derived from 1,4-DICB (i.e. 2,5-DICP) is oxidized to its hydroquinone derivative, which needs prior oxidation in order to generate the reactive benzoquinone species. Residual protein binding in the presence of ascorbic acid could also indicate the involvement of reactive arene oxides in the protein binding of 1,2-DICB, but not of 1,4-DICB. However, MO computer calculations did not provide indications for differences in chemical reactivity and/or stability of the various arene oxide/oxepin tautomers that can be formed from either 1,2-DICB or 1,4-DICB. In conclusion, reactive intermediates in the secondary metabolism of 1,2-DICB lead to more covalent binding than those derived from 1,4-DICB, which correlates very well with their reported hepatotoxic potency." @default.
• W1995819466 created "2016-06-24" @default.
• W1995819466 creator A5032367534 @default.
• W1995819466 creator A5042186897 @default.
• W1995819466 creator A5043640005 @default.
• W1995819466 creator A5080235721 @default.
• W1995819466 creator A5087938003 @default.
• W1995819466 date "1992-11-01" @default.
• W1995819466 modified "2023-09-26" @default.
• W1995819466 title "The involvement of primary and secondary metabolism in the covalent binding of 1,2- and 1,4-dichlorobenzenes" @default.
• W1995819466 cites W1483608598 @default.
• W1995819466 cites W1532212858 @default.
• W1995819466 cites W1775749144 @default.
• W1995819466 cites W1776715443 @default.
• W1995819466 cites W1970931592 @default.
• W1995819466 cites W1973859884 @default.
• W1995819466 cites W1975709468 @default.
• W1995819466 cites W1981730973 @default.
• W1995819466 cites W1988351806 @default.
• W1995819466 cites W1989901385 @default.
• W1995819466 cites W1991053553 @default.
• W1995819466 cites W1997610850 @default.
• W1995819466 cites W2000387356 @default.
• W1995819466 cites W2030991493 @default.
• W1995819466 cites W2049681484 @default.
• W1995819466 cites W2049850901 @default.
• W1995819466 cites W2073092594 @default.
• W1995819466 cites W2081712194 @default.
• W1995819466 cites W2088564728 @default.
• W1995819466 cites W2090121271 @default.
• W1995819466 cites W2120612018 @default.
• W1995819466 cites W2401733296 @default.
• W1995819466 cites W2424391996 @default.
• W1995819466 doi "https://doi.org/10.1016/0009-2797(92)90128-8" @default.
• W1995819466 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/1423744" @default.
• W1995819466 hasPublicationYear "1992" @default.
• W1995819466 type Work @default.
• W1995819466 sameAs 1995819466 @default.
• W1995819466 citedByCount "31" @default.
• W1995819466 countsByYear W19958194662012 @default.
• W1995819466 countsByYear W19958194662013 @default.
• W1995819466 countsByYear W19958194662017 @default.
• W1995819466 crossrefType "journal-article" @default.
• W1995819466 hasAuthorship W1995819466A5032367534 @default.
• W1995819466 hasAuthorship W1995819466A5042186897 @default.
• W1995819466 hasAuthorship W1995819466A5043640005 @default.
• W1995819466 hasAuthorship W1995819466A5080235721 @default.
• W1995819466 hasAuthorship W1995819466A5087938003 @default.
• W1995819466 hasConcept C155647269 @default.
• W1995819466 hasConcept C161790260 @default.
• W1995819466 hasConcept C178790620 @default.
• W1995819466 hasConcept C180577832 @default.
• W1995819466 hasConcept C181199279 @default.
• W1995819466 hasConcept C185592680 @default.
• W1995819466 hasConcept C192937433 @default.
• W1995819466 hasConcept C2777477808 @default.
• W1995819466 hasConcept C2777550763 @default.
• W1995819466 hasConcept C2779686393 @default.
• W1995819466 hasConcept C27881333 @default.
• W1995819466 hasConcept C2986274086 @default.
• W1995819466 hasConcept C31903555 @default.
• W1995819466 hasConcept C55493867 @default.
• W1995819466 hasConcept C62231903 @default.
• W1995819466 hasConcept C71240020 @default.
• W1995819466 hasConcept C87644729 @default.
• W1995819466 hasConceptScore W1995819466C155647269 @default.
• W1995819466 hasConceptScore W1995819466C161790260 @default.
• W1995819466 hasConceptScore W1995819466C178790620 @default.
• W1995819466 hasConceptScore W1995819466C180577832 @default.
• W1995819466 hasConceptScore W1995819466C181199279 @default.
• W1995819466 hasConceptScore W1995819466C185592680 @default.
• W1995819466 hasConceptScore W1995819466C192937433 @default.
• W1995819466 hasConceptScore W1995819466C2777477808 @default.
• W1995819466 hasConceptScore W1995819466C2777550763 @default.
• W1995819466 hasConceptScore W1995819466C2779686393 @default.
• W1995819466 hasConceptScore W1995819466C27881333 @default.
• W1995819466 hasConceptScore W1995819466C2986274086 @default.
• W1995819466 hasConceptScore W1995819466C31903555 @default.
• W1995819466 hasConceptScore W1995819466C55493867 @default.
• W1995819466 hasConceptScore W1995819466C62231903 @default.
• W1995819466 hasConceptScore W1995819466C71240020 @default.
• W1995819466 hasConceptScore W1995819466C87644729 @default.
• W1995819466 hasIssue "3" @default.
• W1995819466 hasLocation W19958194661 @default.
• W1995819466 hasLocation W19958194662 @default.
• W1995819466 hasOpenAccess W1995819466 @default.
• W1995819466 hasPrimaryLocation W19958194661 @default.
• W1995819466 hasRelatedWork W1119809050 @default.
• W1995819466 hasRelatedWork W2086719787 @default.
• W1995819466 hasRelatedWork W2088296677 @default.
• W1995819466 hasRelatedWork W2090709712 @default.
• W1995819466 hasRelatedWork W2120506508 @default.
• W1995819466 hasRelatedWork W2127666162 @default.
• W1995819466 hasRelatedWork W2154227201 @default.
• W1995819466 hasRelatedWork W2325130888 @default.
• W1995819466 hasRelatedWork W2333731204 @default.
• W1995819466 hasRelatedWork W2410564196 @default.
• W1995819466 hasVolume "84" @default.

• next