Tumor initiating activity of 5,11-dimethylchrysene and the structural requirements favoring carcinogenicity of methylated polynuclear aromatic hydrocarbons

Stephen S. Hecht; Shantilal Amin; Abraham Rivenson; Dietrich Hoffmann

doi:10.1016/0304-3835(79)90024-7

Tumor initiating activity of 5,11-dimethylchrysene and the structural requirements favoring carcinogenicity of methylated polynuclear aromatic hydrocarbons

Stephen S. Hecht
, Shantilal Amin
, Abraham Rivenson
, Dietrich Hoffmann

Laboratory Medicine and Pathology

Research output: Contribution to journal › Article › peer-review

45 Scopus citations

Abstract

The tumor initiating activities of 5,11-dimethylchrysene and 5-methylchrysene on mouse skin were compared. After initiating doses of 30 μg or 10 μg, with promotion by 3 times weekly applications of tetradecanoylphorbol acetate, both compounds were highly tumorigenic, inducing tumors in 70-85% of the treated animals. Since 5,12-dimethylchrysene had previously been shown to be only a weak tumor initiator, these results support the generalization that the structural requirements favoring carcinogenicity among the methylated chrysenes and other polynuclear aromatic hydrocarbons (PAH) are a bay region methyl group and a free peri position, both adjacent to an unsubstituted angular ring.

Original language	English (US)
Pages (from-to)	65-70
Number of pages	6
Journal	Cancer Letters
Volume	8
Issue number	1
DOIs	https://doi.org/10.1016/0304-3835(79)90024-7
State	Published - Nov 1979

Bibliographical note

Funding Information:
This study was supported by Grant CA-012376 from the National Cancer Institute. Stephen S. Hecht is recipient of the National Cancer Institute Research Career ~velopment Award No. 5KO4 CA-00124.

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title = "Tumor initiating activity of 5,11-dimethylchrysene and the structural requirements favoring carcinogenicity of methylated polynuclear aromatic hydrocarbons",

abstract = "The tumor initiating activities of 5,11-dimethylchrysene and 5-methylchrysene on mouse skin were compared. After initiating doses of 30 μg or 10 μg, with promotion by 3 times weekly applications of tetradecanoylphorbol acetate, both compounds were highly tumorigenic, inducing tumors in 70-85\% of the treated animals. Since 5,12-dimethylchrysene had previously been shown to be only a weak tumor initiator, these results support the generalization that the structural requirements favoring carcinogenicity among the methylated chrysenes and other polynuclear aromatic hydrocarbons (PAH) are a bay region methyl group and a free peri position, both adjacent to an unsubstituted angular ring.",

author = "Hecht, \{Stephen S.\} and Shantilal Amin and Abraham Rivenson and Dietrich Hoffmann",

note = "Funding Information: This study was supported by Grant CA-012376 from the National Cancer Institute. Stephen S. Hecht is recipient of the National Cancer Institute Research Career \textasciitilde{}velopment Award No. 5KO4 CA-00124.",

year = "1979",

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doi = "10.1016/0304-3835(79)90024-7",

language = "English (US)",

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T1 - Tumor initiating activity of 5,11-dimethylchrysene and the structural requirements favoring carcinogenicity of methylated polynuclear aromatic hydrocarbons

AU - Hecht, Stephen S.

AU - Amin, Shantilal

AU - Rivenson, Abraham

AU - Hoffmann, Dietrich

N1 - Funding Information: This study was supported by Grant CA-012376 from the National Cancer Institute. Stephen S. Hecht is recipient of the National Cancer Institute Research Career ~velopment Award No. 5KO4 CA-00124.

PY - 1979/11

Y1 - 1979/11

N2 - The tumor initiating activities of 5,11-dimethylchrysene and 5-methylchrysene on mouse skin were compared. After initiating doses of 30 μg or 10 μg, with promotion by 3 times weekly applications of tetradecanoylphorbol acetate, both compounds were highly tumorigenic, inducing tumors in 70-85% of the treated animals. Since 5,12-dimethylchrysene had previously been shown to be only a weak tumor initiator, these results support the generalization that the structural requirements favoring carcinogenicity among the methylated chrysenes and other polynuclear aromatic hydrocarbons (PAH) are a bay region methyl group and a free peri position, both adjacent to an unsubstituted angular ring.

AB - The tumor initiating activities of 5,11-dimethylchrysene and 5-methylchrysene on mouse skin were compared. After initiating doses of 30 μg or 10 μg, with promotion by 3 times weekly applications of tetradecanoylphorbol acetate, both compounds were highly tumorigenic, inducing tumors in 70-85% of the treated animals. Since 5,12-dimethylchrysene had previously been shown to be only a weak tumor initiator, these results support the generalization that the structural requirements favoring carcinogenicity among the methylated chrysenes and other polynuclear aromatic hydrocarbons (PAH) are a bay region methyl group and a free peri position, both adjacent to an unsubstituted angular ring.

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U2 - 10.1016/0304-3835(79)90024-7

DO - 10.1016/0304-3835(79)90024-7

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SN - 0304-3835

VL - 8

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JO - Cancer Letters

JF - Cancer Letters

IS - 1

ER -

Tumor initiating activity of 5,11-dimethylchrysene and the structural requirements favoring carcinogenicity of methylated polynuclear aromatic hydrocarbons

Abstract

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