Comparative tumor initiating activities of cyclopentano and methyl derivatives of 5-methylchrysene and chrysene

S. Amin, S. S. Hecht, P. Di Raddo, R. G. Harvey

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Previous studies showed that 5,6-dimethylchrysene (5,6-diMeC) and 5,7-diMec were significantly less tumorigenic than 5-methylchrysene (5-MeC). These results were unexpected based on the known mechanism of metabolic activation of 5-MeC and indicated the presence of critical steric requirements for tumorigenicity at the 6 and 7 positions of 5-MeC. In this study, the structure activity relationships were further extended by comparing the tumor-initiating activities on mouse skin of 5-MeC, 6,7-cyclopentano-5-MeC, 5,6-diMeC, 6,7-diMeC, 5,7-diMeC, chrysene and 6,7-cyclopentanochrysene. 5-MeC was the most tumorigenic compound, with activity significantly higher than all other compounds tested. Among the other compounds, only 5,6-diMeC was significantly tumorigenic. The results demonstrate that substitution of methyl or methylene groups at the 6 or 7 positions of 5-MeC leads to a significant reduction of tumor initiating activity.

Original languageEnglish (US)
Pages (from-to)17-20
Number of pages4
JournalCancer Letters
Issue number1
StatePublished - May 15 1990

Bibliographical note

Funding Information:
We thankV eronicaS aa and BijayaM israf or their technicala ssistanceT. his study was supported by Grant No. CA-44377 from the National Cancer Institutea nd Grant No. ES-04266 from the NationalI nstituteo f Environ-mentalH ealthS ciences.T his is paper no. 133 in “A Study of ChemicalC arcinogenesis”.


  • 5-methylchrysene
  • cyclopentanochrysenes
  • dimethylchrysenes
  • tumor initiation


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