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

doi:10.1093/CARCIN/14.8.1697

Paper

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

Published Aug 1, 1993 · G. Boyd, H. Zepik, L. King

Carcinogenesis

Q1 SJR score

3

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0

Influential Citations

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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.

Study Snapshot

The 11-trifluoromethyl analogue of the potent carcinogen 15,16-dihydro-11-methylcyclopenta[a]-phenanthren-17-one is mutagenic to Salmonella typhimurium TA100 and metabolizes to genotoxic intermediates

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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References

Citations

Stable ion study of protonated cyclopenta[a]phenanthrenes. Structure–reactivity relationships and charge delocalization in the carbocations

Stable ion studies of cyclopenta[a]phenanthrenes reveal their structure-reactivity relationships and charge delocalization in carbocations, providing insights into their biological importance.

Potentially carcinogenic cyclopenta[a]phenanthrenes. Part 13. Synthesis of the 11-trifluoro, 11-cyano, and 11-amino analogues of the carcinogen 15,16-dihydro-11-methylcyclopenta[a]phenanthren-17-one

This study optimizes the synthesis of potentially carcinogenic cyclopenta[a]phenanthrenes by synthesizing 11-trifluoromethyl, 11-cyano, and 11-amino analogues of the carcinogen 15,16-dihydro-11-methylcyclopen

Probing the charge delocalization mode in methyl-, dimethyl- and methylene-bridged phenanthrenium ions. NMR studies of persistent mono- and di-cations and AM1 calculations

The charge delocalization mode in methyl-, dimethyl-, and methylene-bridged phenanthrenium ions is similar to that in methylene-bridged phenanthrene ions, with most observed mono- and di-cations predicted by AM1 to be the most stable.