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Alkylation of Purine Bases by Carbon-Centered Radicals

  • Jae O. Kang
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 366)

Abstract

Mono- and di-substituted hydrazines are found ubiquitously (1, 2). They are present in the environment since they are used as herbicides, chemical intermediates, and as high energy fuels for rockets. They are found in plants such as tobacco and mushrooms. They are also present in medicine. All substituted hydrazines tested for carcinogenicity in long-term animal studies have been found to be positive (1). 1, 2-dimethylhydrazine (DMH) is a well known carcinogen that induces tumors specifically in the colon of rodents (3). Since DMH-induced lesions have characteristics that are remarkably similar to those of human colon cancer, this carcinogen is widely used as a model in the study of colon cancer. The ethyl derivative of DMH, 1, 2-diethylhydrazine (DEH), is also a carcinogen. DEH produces cancer in the thymus, liver, and brain (4). The mechanism(s) by which these di-alkyl hydrazines induce tumors is not known. Kang et al. (5) have shown that in rats the metabolism of DMH and DEH produces methyl radicals (·CH3) and ethyl radicals (·CH2CH3), respectively. Therefore, this investigation was conducted to explore the nature of the chemical interaction(s) between alkyl radicals and biomolecules using CH3 and RNA as models.

Keywords

Alkyl Radical Ethyl Radical Purine Base Chemical Intermediate Chemical Carcinogenesis 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    B. Toth. Synthetic and naturally occurring hydrazines as possible cancer causative agents. Cancer Res. 35:3693 (1975).PubMedGoogle Scholar
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    B. Kalyanaraman and B.K. Sinha. Free radical-mediated activation of hydrazine derivatives. Envir. Health Perspect. 64:179 (1985).CrossRefGoogle Scholar
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    H. Druckrey. Organospecific carcinogenesis, in:“Topics in Chemical Carcinogenesis”, eds. W. Nakahara, S. Takayama, T. Sugimura, and S. Odashima, University Park Press, Baltimore, pp. 87 (1971).Google Scholar
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    K.M. Pozharisski, Y.M. Kapustin, A.J. Likhachev, and J.D. Shaposhnikov. The mechanism of carcinogenic action of 1, 2-dimethylhydrazine (SDMH) in rats. Int. J. Cancer 15:673 (1975).PubMedCrossRefGoogle Scholar
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    J.O. Kang, G. Slater, A.H. Aufses Jr., and G. Cohen (1988). Production of ethane by rats treated with the colon carcinogen, 1, 2-dimethylhydrazine. Biochem. Pharmacol. 37:2967 (1988).PubMedCrossRefGoogle Scholar
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    J.O. Kang, K.S. Gallagher, and G. Cohen. Methylation of RNA purine bases by methyl radicals. Arch. Biochem. Biophys. 306:178 (1993).PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1994

Authors and Affiliations

  • Jae O. Kang
    • 1
  1. 1.Department of Medical Laboratory ScienceUniversity of New HampshireDurhamUSA

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