The biological activity and activation of 15,l6-dihydro-1,11-methanocyclopenta [a] penanthren-17-one, a carcinogen with an obstructed bay region

The proposal that an unobstructed bay region is a prerequisite for tumorigenic activity in cydopenta[a]phenanthrene-17-ones is not supported by the observation of the tumorigenicity of 15,16-dihydro-1,ll-methanocydopenta[a]- phenanthrene-17-one towards the skin of T.O. mice. The title compound is ox...

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Published in:Carcinogenesis (New York) 1984-11, Vol.5 (11), p.1485-1490
Main Authors: Hadfield, Stephen T., Bhatt, Tarlochan S., Coombs, Maurine M.
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container_issue 11
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container_title Carcinogenesis (New York)
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creator Hadfield, Stephen T.
Bhatt, Tarlochan S.
Coombs, Maurine M.
description The proposal that an unobstructed bay region is a prerequisite for tumorigenic activity in cydopenta[a]phenanthrene-17-ones is not supported by the observation of the tumorigenicity of 15,16-dihydro-1,ll-methanocydopenta[a]- phenanthrene-17-one towards the skin of T.O. mice. The title compound is oxidised in vitro by a mixed function oxidase to produce, inter alia, a trans-3,4-dihydrodiol, postulated as the proximate tumorigen. Unequivocal identification of a second metabolite as a trans-1,2-dihydrodiol derivative demonstrates the potential for enzymatic oxidation within the obstructed bay region and supports the proposal that the ultimate tumorigen is a trans-3,4dihydrodiol-anti-l,2-oxide. This is further substantiated by the chromatographic behaviour of the major hydrocarbon-nucleoside adduct derived from mouse skin treated with the parent compound in vivo. The structures of certain others of the metabolite produced in vitro are also considered.
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title The biological activity and activation of 15,l6-dihydro-1,11-methanocyclopenta [a] penanthren-17-one, a carcinogen with an obstructed bay region
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