Synthesis and characterization of oligodeoxynucleotides containing the major DNA adducts formed by 1,6- and 1,8-dinitropyrene.
[reaction: see text] An efficient method for the synthesis of oligonucleotides containing a site-specific DNA adduct formed by the carcinogens 1,6- and 1, 8-dinitropyrene has been developed. Palladium-catalyzed amination provided a straightforward route for the synthesis of aminonitropyrenes which, following separation, were reduced to the nitrosonitropyrenes. The N-hydroxyaminonitropyrene, generated in situ from each nitrosonitropyrene, was used successfully to introduce the dinitropyrene-derived DNA adduct at a defined site in an oligonucleotide.
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Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269, USA.
Basu
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D018736:DNA Adducts / Q000138:chemical synthesis* / Q000187:drug effects; D009153:Mutagens / Q000737:chemistry* / Q000494:pharmacology; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis*; D011721:Pyrenes / Q000737:chemistry* / Q000494:pharmacology
D018736:DNA Adducts; D009153:Mutagens; D009838:Oligodeoxyribonucleotides; D011721:Pyrenes; C033310:1,8-dinitropyrene; C033309:1,6-dinitropyrene