Marked Differences in the Tumor-initiating Activity of Optically Pure (+)- and (−)-trans-7,8-Dihydroxy-7,8-dihydrobenzo(a)pyrene on Mouse Skin

Thomas J Slaga, A. W. Wood, R. L. Chang, H. Yagi, D. M. Jerina, A. H. Conney

Research output: Contribution to journalArticle

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Abstract

The ability of optically pure (+)-and (-)-trans-7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene to initiate skin tumors in mice was determined with a two-stage tumorigenesis system. A single application of 50 to 200 nmoles of (+)-or (-)-trans-7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene to the backs of CD-1 mice followed by twice-weekly applications of 12-0-tetradecanoylphorbol-13-acetate revealed that the (-)-enantiomer was 5-to 10-fold more potent than was the (+)-enantiomer as a tumor initiator at the three dosage levels tested. When the tumor-initiating activities of the (+)-and (-)-enantiomers of trans-7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene were compared to the activity of benzo(a)pyrene at an equimolar dose, the (-)-enantiomer was more active while the (+)-enantiomer was considerably less active. This is the first report of differences in the carcinogenic activity between optical enantiomers.

Original languageEnglish (US)
Pages (from-to)2721-2725
Number of pages5
JournalCancer Research
Volume37
StatePublished - 1977
Externally publishedYes

Fingerprint

Skin
Optical Rotation
Neoplasms
Benzo(a)pyrene
Tetradecanoylphorbol Acetate
Carcinogens
Carcinogenesis
benzo(a)pyrene 7,8-dihydrodiol

ASJC Scopus subject areas

  • Cancer Research
  • Oncology

Cite this

Marked Differences in the Tumor-initiating Activity of Optically Pure (+)- and (−)-trans-7,8-Dihydroxy-7,8-dihydrobenzo(a)pyrene on Mouse Skin. / Slaga, Thomas J; Wood, A. W.; Chang, R. L.; Yagi, H.; Jerina, D. M.; Conney, A. H.

In: Cancer Research, Vol. 37, 1977, p. 2721-2725.

Research output: Contribution to journalArticle

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AU - Wood, A. W.

AU - Chang, R. L.

AU - Yagi, H.

AU - Jerina, D. M.

AU - Conney, A. H.

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