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Syntheses of “unstable” diol epoxide metabolites of the potent carcinogens 7- and 12-methylbenz[a]anthracene
✍ Scribed by Ronald G. Harvey; Cecilia Cortez; Alexander Kiselyov
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- English
- Weight
- 227 KB
- Volume
- 7
- Category
- Article
- ISSN
- 0960-894X
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✦ Synopsis
Stereospecific syntheses of the anti-and syn-diol epoxides of 7-and 12-methylbenz[a]anthracene, suspected as active metabolites of the parent PAHs but previously thought to be too chemically reactive and unstable to isolate, are described and the pure compounds are shown to be moderately stable.
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The racemic anti-dihydrodiol epoxide of 7-methylbenz[a]anthracene preferentially induced mutations at G.C base pairs in the pS189 shuttle vector. Mutations were not randomly distributed throughout the supF target gene, but were concentrated at five hotspots. The hotspots for this agent did not corre