Mutagenic specificities of four stereoisomeric benzo[c]phenanthrene dihydrodiol epoxides.
The pS189 shuttle vector carrying a supF target gene was used to compare the mutagenic specificities of the four configurational isomers of benzo[c]phenanthrene 3,4-dihydrodiol 1,2-epoxide. One of these isomers is the most tumorigenic dihydrodiol epoxide tested to date and another is essentially inactive as a tumorigen. Overall mutagenicities were not correlated with tumorigenicities, but each configurational isomer induced a unique spectrum of mutational hot spots in the supF target gene, which monitors primarily point mutations. It is suggested that the demonstrated isomer-specific selectivity for mutation targets within the supF gene may be indicative of a similar selectivity for one gene versus another and that such selectivity may be one determinant of relative tumorigenicity.
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Chemistry of Carcinogenesis Laboratory, National Cancer Institute-Frederick Cancer Research and Development Center, MD 21702-1201.
St John
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Yagi
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Jerina
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Dipple
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D001483:Base Sequence; D002478:Cells, Cultured; D004252:DNA Mutational Analysis; D016153:Genes, Suppressor; D005822:Genetic Vectors; D066298:In Vitro Techniques; D008969:Molecular Sequence Data; D016296:Mutagenesis; D009153:Mutagens / Q000633:toxicity*; D010616:Phenanthrenes / Q000737:chemistry / Q000633:toxicity*; D012343:RNA, Transfer; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D009153:Mutagens; D010616:Phenanthrenes; C090203:1,2-epoxy-3,4-dihydroxy-1,2,3,4-tetrahydrobenzo(c)phenanthrene; D012343:RNA, Transfer