Skin-tumor-initiating ability of benzo(a)pyrene-7,8-diol-9,10-epoxide (anti) when applied topically in tetrahydrofuran

Thomas J. Slaga; Aurora Viaje; William M. Bracken; David L. Berry; Susan M. Fischer; Don Ray Miller; Susan M. Leclerc

doi:10.1016/S0304-3835(77)93845-9

Skin-tumor-initiating ability of benzo(a)pyrene-7,8-diol-9,10-epoxide (anti) when applied topically in tetrahydrofuran

Thomas J. Slaga, Aurora Viaje, William M. Bracken, David L. Berry, Susan M. Fischer, Don Ray Miller, Susan M. Leclerc

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

48 Scopus citations

Abstract

The skin-tumor-initiating abilities of various metabolites of benzo(a)pyrene (BP) were determined in mice by using a two-stage system of tumorigenesis. We previously reported that BP-7,8-dihydrodiol (± trans) was approximately as potent as BP, suggesting that it may be a proximate carcinogen, but the alleged ultimate carcinogen of BP [BP-7,8-dihydrodiol-9,10-epoxide (anti)] was a weak tumor initiator (Cancer Lett. 2: 115, 1976). Because of its high reactivity, the tumor-initiating ability of the BP-7,8-dihydrodiol-9,10-epoxide (anti) was determined by using acetone, benzene, and tetrahydrofuran (THF) as the solvent vehicles. The 'diol-epoxide' of BP was found to be an effective tumor initiator when applied topically in THF. The effectiveness of the various vehicles for the 'diol-epoxide' was as follows: THF > benzene > acetone; however, acetone was the best solvent for BP tumor initiation. The BP-9,10-dihydrodiol and BP-3-hydroxy were found to be weak tumor initiators. BP-3-hydroxy was also tested for tumor-promoting ability and was found to be inactive in this capacity.

Original language	English (US)
Pages (from-to)	23-30
Number of pages	8
Journal	Cancer Letters
Volume	3
Issue number	C
DOIs	https://doi.org/10.1016/S0304-3835(77)93845-9
State	Published - 1977
Externally published	Yes

ASJC Scopus subject areas

Oncology
Cancer Research

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@article{09c4bc5b4cc44ddda16e5ff235b8a2ea,

title = "Skin-tumor-initiating ability of benzo(a)pyrene-7,8-diol-9,10-epoxide (anti) when applied topically in tetrahydrofuran",

abstract = "The skin-tumor-initiating abilities of various metabolites of benzo(a)pyrene (BP) were determined in mice by using a two-stage system of tumorigenesis. We previously reported that BP-7,8-dihydrodiol (± trans) was approximately as potent as BP, suggesting that it may be a proximate carcinogen, but the alleged ultimate carcinogen of BP [BP-7,8-dihydrodiol-9,10-epoxide (anti)] was a weak tumor initiator (Cancer Lett. 2: 115, 1976). Because of its high reactivity, the tumor-initiating ability of the BP-7,8-dihydrodiol-9,10-epoxide (anti) was determined by using acetone, benzene, and tetrahydrofuran (THF) as the solvent vehicles. The 'diol-epoxide' of BP was found to be an effective tumor initiator when applied topically in THF. The effectiveness of the various vehicles for the 'diol-epoxide' was as follows: THF > benzene > acetone; however, acetone was the best solvent for BP tumor initiation. The BP-9,10-dihydrodiol and BP-3-hydroxy were found to be weak tumor initiators. BP-3-hydroxy was also tested for tumor-promoting ability and was found to be inactive in this capacity.",

author = "Slaga, {Thomas J.} and Aurora Viaje and Bracken, {William M.} and Berry, {David L.} and Fischer, {Susan M.} and Miller, {Don Ray} and Leclerc, {Susan M.}",

note = "Funding Information: * Supported in part by NIH grant CA-20076, and by the Energy Research and Development Administration under contract with Union Carbide Corporation. **DRM is a Predoctoral Fellow supported by Grant GM 1974 from the National Institute of General Medical Sciences, Natidnal Institutes.of Health. SL is a Predoctoral Fellow supported by Grant CAO-9104 from the National Cancer Institute. -~Abbreviations: BP, benzo(a)pyrene; BP-7,8-diol, BP-7,8-dihydrodiol (_* trans); BP-diolepoxide, BP:7,8-dihydrodiol-9,19~epoxide (anti); BP-9,10-diol, BP-9,10-dihydrodiol; BP-3-OH, BP-3-hydroxy ; TPA, 12-O-tetradecanoylphorbol-13-acetate; THF, tetrahydrofuran.",

year = "1977",

doi = "10.1016/S0304-3835(77)93845-9",

language = "English (US)",

volume = "3",

pages = "23--30",

journal = "Cancer Letters",

issn = "0304-3835",

publisher = "Elsevier Ireland Ltd",

number = "C",

}

TY - JOUR

T1 - Skin-tumor-initiating ability of benzo(a)pyrene-7,8-diol-9,10-epoxide (anti) when applied topically in tetrahydrofuran

AU - Slaga, Thomas J.

AU - Viaje, Aurora

AU - Bracken, William M.

AU - Berry, David L.

AU - Fischer, Susan M.

AU - Miller, Don Ray

AU - Leclerc, Susan M.

N1 - Funding Information: * Supported in part by NIH grant CA-20076, and by the Energy Research and Development Administration under contract with Union Carbide Corporation. **DRM is a Predoctoral Fellow supported by Grant GM 1974 from the National Institute of General Medical Sciences, Natidnal Institutes.of Health. SL is a Predoctoral Fellow supported by Grant CAO-9104 from the National Cancer Institute. -~Abbreviations: BP, benzo(a)pyrene; BP-7,8-diol, BP-7,8-dihydrodiol (_* trans); BP-diolepoxide, BP:7,8-dihydrodiol-9,19~epoxide (anti); BP-9,10-diol, BP-9,10-dihydrodiol; BP-3-OH, BP-3-hydroxy ; TPA, 12-O-tetradecanoylphorbol-13-acetate; THF, tetrahydrofuran.

PY - 1977

Y1 - 1977

N2 - The skin-tumor-initiating abilities of various metabolites of benzo(a)pyrene (BP) were determined in mice by using a two-stage system of tumorigenesis. We previously reported that BP-7,8-dihydrodiol (± trans) was approximately as potent as BP, suggesting that it may be a proximate carcinogen, but the alleged ultimate carcinogen of BP [BP-7,8-dihydrodiol-9,10-epoxide (anti)] was a weak tumor initiator (Cancer Lett. 2: 115, 1976). Because of its high reactivity, the tumor-initiating ability of the BP-7,8-dihydrodiol-9,10-epoxide (anti) was determined by using acetone, benzene, and tetrahydrofuran (THF) as the solvent vehicles. The 'diol-epoxide' of BP was found to be an effective tumor initiator when applied topically in THF. The effectiveness of the various vehicles for the 'diol-epoxide' was as follows: THF > benzene > acetone; however, acetone was the best solvent for BP tumor initiation. The BP-9,10-dihydrodiol and BP-3-hydroxy were found to be weak tumor initiators. BP-3-hydroxy was also tested for tumor-promoting ability and was found to be inactive in this capacity.

AB - The skin-tumor-initiating abilities of various metabolites of benzo(a)pyrene (BP) were determined in mice by using a two-stage system of tumorigenesis. We previously reported that BP-7,8-dihydrodiol (± trans) was approximately as potent as BP, suggesting that it may be a proximate carcinogen, but the alleged ultimate carcinogen of BP [BP-7,8-dihydrodiol-9,10-epoxide (anti)] was a weak tumor initiator (Cancer Lett. 2: 115, 1976). Because of its high reactivity, the tumor-initiating ability of the BP-7,8-dihydrodiol-9,10-epoxide (anti) was determined by using acetone, benzene, and tetrahydrofuran (THF) as the solvent vehicles. The 'diol-epoxide' of BP was found to be an effective tumor initiator when applied topically in THF. The effectiveness of the various vehicles for the 'diol-epoxide' was as follows: THF > benzene > acetone; however, acetone was the best solvent for BP tumor initiation. The BP-9,10-dihydrodiol and BP-3-hydroxy were found to be weak tumor initiators. BP-3-hydroxy was also tested for tumor-promoting ability and was found to be inactive in this capacity.

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U2 - 10.1016/S0304-3835(77)93845-9

DO - 10.1016/S0304-3835(77)93845-9

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AN - SCOPUS:0017682857

VL - 3

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JO - Cancer Letters

JF - Cancer Letters

SN - 0304-3835

IS - C

ER -

Skin-tumor-initiating ability of benzo(a)pyrene-7,8-diol-9,10-epoxide (anti) when applied topically in tetrahydrofuran

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