Tumour initiating activity of dihydrodiols of benzo[b]fluoranthene, benzo[j]fluoranthene, and benzo[k]fluoranthene

Edmond J. Lavole, Shantu Amin, Stephen S. Hecht, Keizo Furuya, Dietrich Hoffmann

Research output: Contribution to journalArticle

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Abstract

The tumor initiating activities on mouse skin of benzo[b]fluoranthene, (B[b]F), benzo[j]fluoranthene (B[b]F), benzo[k]fluoranthene (B[k]F) and three of their dihydrodiols-9,10-dihydro-9,10-dihydroxybenzo[b]fluoranthene (B[b]F-9,10-diol), 9,10-dihydro-9,10-dihydroxybenzo[j]fluoranthene (B[j]F-9,10-diol), and 8,9-dihydro-8,9-dihydroxybenzo[k]fluoranthene (B[k]F-8,9-diol) were evaluated. Among the parent hydrocarbons, B[b]F was the most potent tumor initiator, with activity greater than that of B(j]F but less than that of benzo[a]pyrene. B[k]F also showed tumor initiating activity, in contrast to its lack of complete carcinogenic activity on mouse skin. B[b]F-9, 10-diol, which can form a bay region dihydrodiol epoxide, was as active as B[b]F. B[j]F-9, 10-diol, which would form its dihydrodiol epoxide in a four sided pseudo-bay region, was less active than B[j]F. B[k]F-8,9-diol was inactive. These results, together with parallel metabolic studies, suggest that the formation of bay region dihydrodiol epoxides may not be the major activation mechanism in benzofluoranthene tumorigenesis.

Original languageEnglish (US)
Pages (from-to)49-52
Number of pages4
JournalCarcinogenesis
Volume3
Issue number1
DOIs
StatePublished - Dec 1 1982

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Epoxy Compounds
Neoplasms
Skin
Benzo(a)pyrene
Hydrocarbons
Carcinogens
Carcinogenesis
benzo(k)fluoranthene
benzo(b)fluoranthene
benzo(j)fluoranthene
trans-1,2-dihydro-1,2-naphthalenediol
9,10-dihydro-9,10-dihydroxybenzo(j)fluoranthene

All Science Journal Classification (ASJC) codes

  • Cancer Research

Cite this

Lavole, Edmond J. ; Amin, Shantu ; Hecht, Stephen S. ; Furuya, Keizo ; Hoffmann, Dietrich. / Tumour initiating activity of dihydrodiols of benzo[b]fluoranthene, benzo[j]fluoranthene, and benzo[k]fluoranthene. In: Carcinogenesis. 1982 ; Vol. 3, No. 1. pp. 49-52.
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abstract = "The tumor initiating activities on mouse skin of benzo[b]fluoranthene, (B[b]F), benzo[j]fluoranthene (B[b]F), benzo[k]fluoranthene (B[k]F) and three of their dihydrodiols-9,10-dihydro-9,10-dihydroxybenzo[b]fluoranthene (B[b]F-9,10-diol), 9,10-dihydro-9,10-dihydroxybenzo[j]fluoranthene (B[j]F-9,10-diol), and 8,9-dihydro-8,9-dihydroxybenzo[k]fluoranthene (B[k]F-8,9-diol) were evaluated. Among the parent hydrocarbons, B[b]F was the most potent tumor initiator, with activity greater than that of B(j]F but less than that of benzo[a]pyrene. B[k]F also showed tumor initiating activity, in contrast to its lack of complete carcinogenic activity on mouse skin. B[b]F-9, 10-diol, which can form a bay region dihydrodiol epoxide, was as active as B[b]F. B[j]F-9, 10-diol, which would form its dihydrodiol epoxide in a four sided pseudo-bay region, was less active than B[j]F. B[k]F-8,9-diol was inactive. These results, together with parallel metabolic studies, suggest that the formation of bay region dihydrodiol epoxides may not be the major activation mechanism in benzofluoranthene tumorigenesis.",
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Tumour initiating activity of dihydrodiols of benzo[b]fluoranthene, benzo[j]fluoranthene, and benzo[k]fluoranthene. / Lavole, Edmond J.; Amin, Shantu; Hecht, Stephen S.; Furuya, Keizo; Hoffmann, Dietrich.

In: Carcinogenesis, Vol. 3, No. 1, 01.12.1982, p. 49-52.

Research output: Contribution to journalArticle

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N2 - The tumor initiating activities on mouse skin of benzo[b]fluoranthene, (B[b]F), benzo[j]fluoranthene (B[b]F), benzo[k]fluoranthene (B[k]F) and three of their dihydrodiols-9,10-dihydro-9,10-dihydroxybenzo[b]fluoranthene (B[b]F-9,10-diol), 9,10-dihydro-9,10-dihydroxybenzo[j]fluoranthene (B[j]F-9,10-diol), and 8,9-dihydro-8,9-dihydroxybenzo[k]fluoranthene (B[k]F-8,9-diol) were evaluated. Among the parent hydrocarbons, B[b]F was the most potent tumor initiator, with activity greater than that of B(j]F but less than that of benzo[a]pyrene. B[k]F also showed tumor initiating activity, in contrast to its lack of complete carcinogenic activity on mouse skin. B[b]F-9, 10-diol, which can form a bay region dihydrodiol epoxide, was as active as B[b]F. B[j]F-9, 10-diol, which would form its dihydrodiol epoxide in a four sided pseudo-bay region, was less active than B[j]F. B[k]F-8,9-diol was inactive. These results, together with parallel metabolic studies, suggest that the formation of bay region dihydrodiol epoxides may not be the major activation mechanism in benzofluoranthene tumorigenesis.

AB - The tumor initiating activities on mouse skin of benzo[b]fluoranthene, (B[b]F), benzo[j]fluoranthene (B[b]F), benzo[k]fluoranthene (B[k]F) and three of their dihydrodiols-9,10-dihydro-9,10-dihydroxybenzo[b]fluoranthene (B[b]F-9,10-diol), 9,10-dihydro-9,10-dihydroxybenzo[j]fluoranthene (B[j]F-9,10-diol), and 8,9-dihydro-8,9-dihydroxybenzo[k]fluoranthene (B[k]F-8,9-diol) were evaluated. Among the parent hydrocarbons, B[b]F was the most potent tumor initiator, with activity greater than that of B(j]F but less than that of benzo[a]pyrene. B[k]F also showed tumor initiating activity, in contrast to its lack of complete carcinogenic activity on mouse skin. B[b]F-9, 10-diol, which can form a bay region dihydrodiol epoxide, was as active as B[b]F. B[j]F-9, 10-diol, which would form its dihydrodiol epoxide in a four sided pseudo-bay region, was less active than B[j]F. B[k]F-8,9-diol was inactive. These results, together with parallel metabolic studies, suggest that the formation of bay region dihydrodiol epoxides may not be the major activation mechanism in benzofluoranthene tumorigenesis.

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