Comparative Tumorigenicity of Dimethylchrysenes in Mouse Skin

Shantu Amin, Dhimant Desai, Stephen S. Hecht

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

In previous studies, we have observed unexpected structure-tumorigenicity relationships among the dimethylchrysenes. Thus, 5,6-dimethylchrysene and 5,7-dimethylchrysene were only weakly tumorigenic and were significantly less active than 5-methylchrysene. These results were surprising in view of the known route of metabolic activation of 5-methylchrysene via its 1,2-diol 3,4-epoxide. In this paper, we extended our studies of structure-tumorigenicity relationships among the dimethylchrysenes. We synthesized 5,7-, 5,8-, 5,9-, and 5,10-dimethylchrysene via photochemical ring closure reactions. The tumor-initiating activities of these dimethylchrysenes on mouse skin were compared with those of 5-methylchrysene and 5,6-dimethylchrysene. 5- Methylchrysene and 5,9-dimethylchrysene were highly tumorigenic and were significantly more active than 5,6-, 5,7-, 5,8-, and 5,10-dimethylchrysene. The results of these studies, taken together with those reported in the subsequent two papers, suggest that the molecular shapes of dimethylchrysenes influence the balance between metabolic activation and detoxification pathways.

Original languageEnglish (US)
Pages (from-to)237-241
Number of pages5
JournalChemical Research in Toxicology
Volume5
Issue number2
DOIs
StatePublished - Mar 1 1992

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Skin
Chemical activation
Detoxification
Epoxy Compounds
Tumors
5-methylchrysene
Neoplasms
5,6-dimethylchrysene
Metabolic Activation

All Science Journal Classification (ASJC) codes

  • Toxicology

Cite this

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abstract = "In previous studies, we have observed unexpected structure-tumorigenicity relationships among the dimethylchrysenes. Thus, 5,6-dimethylchrysene and 5,7-dimethylchrysene were only weakly tumorigenic and were significantly less active than 5-methylchrysene. These results were surprising in view of the known route of metabolic activation of 5-methylchrysene via its 1,2-diol 3,4-epoxide. In this paper, we extended our studies of structure-tumorigenicity relationships among the dimethylchrysenes. We synthesized 5,7-, 5,8-, 5,9-, and 5,10-dimethylchrysene via photochemical ring closure reactions. The tumor-initiating activities of these dimethylchrysenes on mouse skin were compared with those of 5-methylchrysene and 5,6-dimethylchrysene. 5- Methylchrysene and 5,9-dimethylchrysene were highly tumorigenic and were significantly more active than 5,6-, 5,7-, 5,8-, and 5,10-dimethylchrysene. The results of these studies, taken together with those reported in the subsequent two papers, suggest that the molecular shapes of dimethylchrysenes influence the balance between metabolic activation and detoxification pathways.",
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Comparative Tumorigenicity of Dimethylchrysenes in Mouse Skin. / Amin, Shantu; Desai, Dhimant; Hecht, Stephen S.

In: Chemical Research in Toxicology, Vol. 5, No. 2, 01.03.1992, p. 237-241.

Research output: Contribution to journalArticle

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