Mutagenic specificities of four stereoisomeric benzo[c]phenanthrene dihydrodiol epoxides.
نویسندگان
چکیده
منابع مشابه
Mutagenicity of dihydrodiols and diol epoxides of dibenz[a, h]acridine in bacterial and mammalian cells.
Bay-region diol epoxides are ultimate carcinogenic metabolites of a number of polycyclic aromatic compounds. Dibenz[a, h]acridine can form two diastereomeric pairs of these diol epoxides which are not positionally equivalent as a result of the nitrogen atom at position 7. We have assessed the structure-activity relationships resulting from heterocyclic nitrogen substitution by examining the mut...
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Metabolism of benzo[e]pyrene 9,10-dihydrodiol to the bay-region 9,10-diol-11,12-epoxides by hepatic microsomes from human, rat, mouse, guinea pig, hamster, and rabbit has been examined in the presence and absence of 7,8-benzoflavone. In the absence of 7,8-benzoflavone, the formation of bay-region diol epoxides from benzo[e]pyrene 9,10-dihydrodiol was low in all species except the hamster. With ...
متن کاملMutagenic and cell-transforming activities of triol-epoxides as compared to other chrysene metabolites.
The syn- and anti-isomers of the bay-region diol-epoxides of chrysene and of 3-hydroxychrysene and their metabolic precursors have been investigated for mutagenicity in Salmonella typhimurium (reversion to histidine prototrophy) and V79 Chinese hamster cells (acquirement of resistance to 6-thioguanine) and for transforming activity in M2 mouse prostate cells. Other known and potential chrysene ...
متن کاملTumorigenicity of bay-region epoxides and other derivatives of chrysene and phenanthrene in newborn mice.
nogenic activity (4). Chrysene, which has one more benzene ring than does phenanthrene, is a symmetrical molecule with 2 identical bay regions (Chart 1). Chrysene has weak activity in carcinogenicity tests (4, 11). Quantum mechanical aspects of the bay region theory predict (6) that bay-region 1,2-diol 3,4-epoxides of chrysene and phenanthrene should have sim ilar chemical reactivities. Kinetic...
متن کاملStructure elucidation of the adducts formed by fjord-region Dibenzo[a,l]pyrene 11,12-dihydrodiol 13,14-epoxides and deoxyadenosine.
Model adducts to be used in the identification of biologically formed adducts were synthesized by reaction of fjord-region dibenzo[a,l]pyrene 11,12-dihydrodiol 13,14-epoxides (DB[a,l]PDE) and deoxyadenosine (dA). The (+/-)-anti-DB[a,l]PDE was reacted with dA in dimethylformamide at 100 degrees C for 30 min to give four DB[a, l]PDE-14-N(6)dA adducts: (-)-anti-trans (26%), (+)-anti-trans (26%), (...
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ژورنال
عنوان ژورنال: Proceedings of the National Academy of Sciences
سال: 1992
ISSN: 0027-8424,1091-6490
DOI: 10.1073/pnas.89.1.368