Abstract
BIOLOGICAL alkylating agents—“mustards”, ethylenimines, epoxides and alkyl alkanesulphonates—have been believed to induce mutations by causing atypical base pairing during DNA replication at sites bearing a guanine residue which has suffered alkylation at the 7(N) position1,2. The most abundant reaction product found in acid hydrolysates of treated DNA is 7-alkyl guanine3,4, although alkylated adenines and cytosine, notably 3-alkyl adenine, are recovered as minor products. Furthermore, genetic studies of alkylation mutants in bacteria and bacteriophages have shown that many point mutational events involve guanine to adenine transitions5,6.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 51 print issues and online access
$199.00 per year
only $3.90 per issue
Buy this article
- Purchase on Springer Link
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
Similar content being viewed by others
References
Lawley, P. D., and Brookes, P., Nature, 192, 1081 (1961).
Nagata, C., Imamura, A., Saito, H., and Fukui, K., Gann., 54, 109 (1963).
Brookes, P. D., and Lawley, P., Biochem. J., 80, 496 (1961).
Lawley, P. D., Prog. Nucleic Acid Res., and Mol. Biol., 5, 89 (1966).
Krieg, D. R., Genetics, 48, 561 (1963).
Osborn, Mary, Person, S., Phillips, S., and Funk, F., J. Mol. Biol., 26, 437 (1967).
Brookes, P., and Lawley, P. D., Biochem. J., 89, 138 (1963).
Loveless, A., Proc. Roy. Soc. B., 150, 497 (1959).
Loveless, A., and Hampton, C. L., Mutation Res., 7, 1 (1969).
Kriek, E., and Emmelot, P., Biochim. Biophys. Acta, 91, 59 (1964).
Friedman, O. M., Malapatra, G. N., and Stevenson, R., Biochim. Biophys. Acta, 68, 144 (1963).
Friedman, O. M., Malapatra, G. N., Dash, B., and Stevenson, R., Biochim. Biophys. Acta, 103, 286 (1965).
Miles, H. T., J. Org. Chem., 26, 4761 (1961).
Schiet, K-H., and Holy, A., Biochim. Biophys. Acta, 149, 344 (1967).
Lawley, P. D., Proc. Chem. Soc., 290 (1957).
Markham, R., and Smith, J. D., Biochem. J., 49, 401 (1951).
Gerster, J. F., Jones, J. W., and Robins, R. K., J. Org. Chem., 28, 945 (1963).
Swann, P. F., and Magee, P. N., Biochem. J., 110, 39 (1968).
Krüger, F. W., Ballweg, H., and Maier-Borst, W., Experientia, 24, 592 (1968).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
LOVELESS, A. Possible Relevance of O–6 Alkylation of Deoxyguanosine to the Mutagenicity and Carcinogenicity of Nitrosamines and Nitrosamides. Nature 223, 206–207 (1969). https://doi.org/10.1038/223206a0
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1038/223206a0
This article is cited by
-
N-Methyl-N-nitrosourea as a mammary carcinogenic agent
Tumor Biology (2015)
-
Theoretical study on the detailed repair of O6-methyl guanine to guanine by cysteine
Journal of Chemical Sciences (2014)
-
Comparison of gas phase intrinsic properties of cytosine and thymine nucleobases with their O-alkyl adducts: different hydrogen bonding preferences for thymine versus O-alkyl thymine
Journal of Molecular Modeling (2013)
-
Quasi-Adaptive Response to Alkylating Agents in Escherichia coli: A New Phenomenon
Russian Journal of Genetics (2005)
-
Isolation by phage display and characterization of a single-chain antibody specific for O6-methyldeoxyguanosine
Chinese Science Bulletin (2001)
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.
