The in vitro metabolic activation of the 11-trifluoromethyl analogue of the potent carcinogen 15,16-dihydro-11-methylcyclopenta[a]phenanthren-17-one to mutagens

Gary Boyd, Helmut H Zepik, Lloyd M King, Costas Ioannides, Maurice M Coombs

Research output: Contribution to journalArticle

Abstract

A strongly electronegative, bay-region analogue of the potent carcinogen 15, 16-dihydro-11-methylcyclopenta[a]phenanthren-17-one, namely 15, 16-dihydro-11-trifluoromethylcyclopenta[a]phenanthren-17-one, is mutagenic to Salmonella typhimurium TA100. Also it is metabolized at the 1, 2- and 3, 4-positions in the A-ring as well as C-15 in the D-ring to give 3, 4-dihydroxy-3, 4, 15, 16-tetrahydro-11-trifluoromethyl-cyclopenta[a]phenanthren-17-one as the only mutagenic metabolite. In these respects its behaviour is closely similar to that of the 11-methyl compound, suggesting that the electronic nature of the bay-region substituent is rather less critical than its spatial configuration in influencing metabolism to genotoxic intermediates. It remains to be seen, however, whether the trifluoromethyl compound is also a carcinogen.
Original languageEnglish
Pages (from-to)1697-1699
JournalCarcinogenesis
Volume14
Issue number8
DOIs
Publication statusPublished - Aug 1993
Externally publishedYes

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Mutagens
Carcinogens
Salmonella typhimurium
Metabolic Activation
15,16-dihydro-11-methylcyclopenta(a)phenanthren-17-one
In Vitro Techniques
C 15

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Boyd, Gary ; Zepik, Helmut H ; King, Lloyd M ; Ioannides, Costas ; Coombs, Maurice M. / The in vitro metabolic activation of the 11-trifluoromethyl analogue of the potent carcinogen 15,16-dihydro-11-methylcyclopenta[a]phenanthren-17-one to mutagens. In: Carcinogenesis. 1993 ; Vol. 14, No. 8. pp. 1697-1699.
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abstract = "A strongly electronegative, bay-region analogue of the potent carcinogen 15, 16-dihydro-11-methylcyclopenta[a]phenanthren-17-one, namely 15, 16-dihydro-11-trifluoromethylcyclopenta[a]phenanthren-17-one, is mutagenic to Salmonella typhimurium TA100. Also it is metabolized at the 1, 2- and 3, 4-positions in the A-ring as well as C-15 in the D-ring to give 3, 4-dihydroxy-3, 4, 15, 16-tetrahydro-11-trifluoromethyl-cyclopenta[a]phenanthren-17-one as the only mutagenic metabolite. In these respects its behaviour is closely similar to that of the 11-methyl compound, suggesting that the electronic nature of the bay-region substituent is rather less critical than its spatial configuration in influencing metabolism to genotoxic intermediates. It remains to be seen, however, whether the trifluoromethyl compound is also a carcinogen.",
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The in vitro metabolic activation of the 11-trifluoromethyl analogue of the potent carcinogen 15,16-dihydro-11-methylcyclopenta[a]phenanthren-17-one to mutagens. / Boyd, Gary; Zepik, Helmut H; King, Lloyd M; Ioannides, Costas; Coombs, Maurice M.

In: Carcinogenesis, Vol. 14, No. 8, 08.1993, p. 1697-1699.

Research output: Contribution to journalArticle

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