Isotope effect on the carcinogenicity of 3-methylcholanthrene in mouse skin by selective deuteration of the 1-methylene group: Biological evidence for a mechanism of tumor initiation

Ercole Cavalieri, H. Garcia, P. Mailander, K. Patil

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9 Citations (Scopus)

Abstract

3-MethylchoIanthrene (MC) in chloroform and trifluoroacetic acid-d1 yielded 3-methylcholanthrene-d4 (MC-d4), a compound selectively deuterated at the 1-, 5-, and 6-carbon atoms. In turn, the protodedeuteration of the labeled hydrocarbon at the 6-carbon atom led to 3-methyleholanthrene-d3 (MC-d3). A comparative test for carcinogenicity between MC and MC-d3 by repeated skin painting on female Swiss mice showed a significantly lower tumorigenic activity of the latter. The result implies that the 1-carbon atom of the hydrocarbon is a critical binding-site to cellular targets in the tumor-initiating process.

Original languageEnglish (US)
Pages (from-to)179-189
Number of pages11
JournalChemico-Biological Interactions
Volume11
Issue number3
DOIs
StatePublished - Sep 1975

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Methylcholanthrene
Isotopes
Tumors
Skin
Carbon
Hydrocarbons
Atoms
Carcinogenicity Tests
Trifluoroacetic Acid
Neoplasms
Paintings
Painting
Chloroform
Binding Sites

ASJC Scopus subject areas

  • Toxicology

Cite this

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title = "Isotope effect on the carcinogenicity of 3-methylcholanthrene in mouse skin by selective deuteration of the 1-methylene group: Biological evidence for a mechanism of tumor initiation",
abstract = "3-MethylchoIanthrene (MC) in chloroform and trifluoroacetic acid-d1 yielded 3-methylcholanthrene-d4 (MC-d4), a compound selectively deuterated at the 1-, 5-, and 6-carbon atoms. In turn, the protodedeuteration of the labeled hydrocarbon at the 6-carbon atom led to 3-methyleholanthrene-d3 (MC-d3). A comparative test for carcinogenicity between MC and MC-d3 by repeated skin painting on female Swiss mice showed a significantly lower tumorigenic activity of the latter. The result implies that the 1-carbon atom of the hydrocarbon is a critical binding-site to cellular targets in the tumor-initiating process.",
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T1 - Isotope effect on the carcinogenicity of 3-methylcholanthrene in mouse skin by selective deuteration of the 1-methylene group

T2 - Biological evidence for a mechanism of tumor initiation

AU - Cavalieri, Ercole

AU - Garcia, H.

AU - Mailander, P.

AU - Patil, K.

PY - 1975/9

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N2 - 3-MethylchoIanthrene (MC) in chloroform and trifluoroacetic acid-d1 yielded 3-methylcholanthrene-d4 (MC-d4), a compound selectively deuterated at the 1-, 5-, and 6-carbon atoms. In turn, the protodedeuteration of the labeled hydrocarbon at the 6-carbon atom led to 3-methyleholanthrene-d3 (MC-d3). A comparative test for carcinogenicity between MC and MC-d3 by repeated skin painting on female Swiss mice showed a significantly lower tumorigenic activity of the latter. The result implies that the 1-carbon atom of the hydrocarbon is a critical binding-site to cellular targets in the tumor-initiating process.

AB - 3-MethylchoIanthrene (MC) in chloroform and trifluoroacetic acid-d1 yielded 3-methylcholanthrene-d4 (MC-d4), a compound selectively deuterated at the 1-, 5-, and 6-carbon atoms. In turn, the protodedeuteration of the labeled hydrocarbon at the 6-carbon atom led to 3-methyleholanthrene-d3 (MC-d3). A comparative test for carcinogenicity between MC and MC-d3 by repeated skin painting on female Swiss mice showed a significantly lower tumorigenic activity of the latter. The result implies that the 1-carbon atom of the hydrocarbon is a critical binding-site to cellular targets in the tumor-initiating process.

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