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Research Article

Synthesis and analysis of DNA adducts of arylamines

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Pages 9-20 | Received 20 Sep 1995, Accepted 25 Oct 1995, Published online: 27 Sep 2008
 

Abstract

Atylamines and nitroarenes are very important environmental and occupational pollutants. Genotoxic effects of arylamines are believed to be initiated by the formation of DNA adducts. DNA adducts of arylamines have been found in experimental animals and in exposed humans, and are predominantly formed with the carbon 8 of 2′-deoxyguanosine. Reference standards are necessary to develop methods for the quantification of DNA-adducts. Therefore, we have synthesized the 2′-deoxyguanosin-8-yI adducts of 2-methylaniline, 2-chloroaniline, 4-chloroaniline, 2,4dimethylaniline, and 2,6-dimethylaniline. The products were characterized by 1H-NMR, 13C-NMR, MS and UV. The corresponding 2′-deoxyguanosine-3′ -monophosphate adducts were synthesized for the quantification of DNA adducts by the 32P-postlabelling technique. A GC-MS method was developed for the analysis of the new adducts as an alternative to the 32P-postlabelling. DNA was spiked with the synthesized adducts and treated with 0.3 m NaOH overnight at 110 °C in the presence of a deuterated internal standard. We observed up to 80% recovery from about 1 adduct in 108 to 1 in 105 nucleotides.

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