Assessment of diphenylcyclopropenone for photochemically induced mutagenicity in the Ames assay

Michael Wilkerson, Thomas H. Connor, Jack Henkin, Jonathan K. Wilkin, Thomas S. Matney

Research output: Contribution to journalArticle

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Abstract

The photochemical conversion of diphenylcyclopropenone to diphenylacetylene has recently been reported. Diphenylcyclopropenone is used in the treatment of alopecia areata and is nonmutagenic in a limited Ames assay. We examined diphenylcyclopropenone and diphenylacetylene, as well as synthetic precursors of diphenylcyclopropenone - dibenzylketone and α,α'-dibromodibenzylketone - for mutagenicity against TA100, TA98, TA102, UTH8413, and UTH8414. All compounds were nonmutagenic except α,α'-dibromodibenzylketone, which was a potent mutagen in TA100 with and without S-9 activation. The effect of photochemical activation of diphenylcyclopropenone in the presence of bacteria demonstrated mutagenicity in UTH8413 (two times background) at 10 μg/plate with S-9 microsomal activation. 8-Methoxypsoralen produces a mutagenic response in TA102 at 0.1 μg/plate with 60 seconds of exposure to 350 nm light. In vitro photochemically activated Ames assay with S-9 microsomal fraction may enhance the trapping of short-lived photochemically produced high-energy mutagenic intermediates. This technique offers exciting opportunities to trap high-energy intermediates that may play an important role in mutagenesis. This method can be applied to a variety of topically applied dermatologic agents, potentially subjected to photochemical changes in normal use.

Original languageEnglish (US)
Pages (from-to)606-611
Number of pages6
JournalJournal of the American Academy of Dermatology
Volume17
Issue number4
DOIs
StatePublished - 1987
Externally publishedYes

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Dermatologic Agents
Methoxsalen
Alopecia Areata
Mutagens
Mutagenesis
diphenylcyclopropenone
Bacteria
Light
biphenylacetylene
In Vitro Techniques

ASJC Scopus subject areas

  • Dermatology

Cite this

Assessment of diphenylcyclopropenone for photochemically induced mutagenicity in the Ames assay. / Wilkerson, Michael; Connor, Thomas H.; Henkin, Jack; Wilkin, Jonathan K.; Matney, Thomas S.

In: Journal of the American Academy of Dermatology, Vol. 17, No. 4, 1987, p. 606-611.

Research output: Contribution to journalArticle

Wilkerson, Michael ; Connor, Thomas H. ; Henkin, Jack ; Wilkin, Jonathan K. ; Matney, Thomas S. / Assessment of diphenylcyclopropenone for photochemically induced mutagenicity in the Ames assay. In: Journal of the American Academy of Dermatology. 1987 ; Vol. 17, No. 4. pp. 606-611.
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