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- W2184728709 abstract "The mutagenic activities of the diol-epoxide and tetrahydro epoxide derivatives of benzo(e)pyreneand triphenylene were assessed in bacterial and mammaliancells to help determine why these two structurally related polycyclic hydrocarbons have little if any carcinogenic activity. In strains TA98 and TA100 of Salmonella typhimurium, a 400-fold range in muta genic activities of the epoxide derivatives was observed under conditions in which all of the compounds induced significant dose-dependentmutationfrequencies.Thediastereomericpair of diol-epoxides of benzo(e)pyrene were 4- to 8-fold more mutagenic than the diastereomeric pair of diol-epoxides of triphenylene.Thecorrespondingtetrahydroepoxidederivatives of both hydrocarbons, in which the hydroxyl groups were absent from the saturated benzo ring, were from 10 to 400 times more mutagenicthan were the corresponding diol-epox ides. Qualitatively similar results were observed with cultured ChinesehamsterV79 cells except that the diastereomeric pair of diol-epoxides of triphenylene had insignificant mutagenic and cytotoxic activity toward the mammaliancells. A plausible explanation for the relatively low mutagenic activities of the diol-epoxides relative to their tetrahydroepoxides is that the hydroxyl groups interfere with the accessibility to or the critical interaction with cellular DNA. Inability of trans-i ,2-dihydroxy 1,2-dihydrotriphenylene, the potential metabolic precursor of the triphenylenediol-epoxides, to be metabolicallyactivated by rat liver microsomesto bacterial mutagens is probably a con sequence of the quasidiaxial conformation of the hydroxyl groups in this dihydrodiol." @default.
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- W2184728709 date "1985-01-01" @default.
- W2184728709 modified "2023-09-24" @default.
- W2184728709 title "Mutagenicityof Benzo(e)pyreneandTriphenyleneTetrahydroepoxides and Diol-Epoxides in Bacterialand MammalianCells" @default.
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