PMID: 2125491Nov 20, 1990Paper

Intercalation of aflatoxin B1 in two oligodeoxynucleotide adducts: comparative 1H NMR analysis of d(ATCAFBGAT).d(ATCGAT) and d(ATAFBGCAT)2

Biochemistry
S GopalakrishnanM P Stone

Abstract

8,9-Dihydro-8-(N7-guanyl-[d(ATCGAT)])-9-hydroxyaflatoxin B1.d(ATCGAT) and 8,9-dihydro-8-(N7-guanyl-[d(ATGCAT)])-9-hydroxyaflatoxin B1.8,9-dihydro-8-(N7-guanyl-[d(ATGCAT)])-9-hydroxyaflatoxin B1 were prepared by direct addition of afltoxin B1 8,9-epoxide to d(ATCGAT)2 and d(ATGCAT)2, respectively. In contrast to reaction of aflatoxin B1 8,9-epoxide with d(ATCGAT)2 which exhibits a limiting stoichiometry of 1:1 aflatoxin B1:d(ATCGAT)2 [Gopalakrishnan, S., Stone, M. P., & Harris, T. M. (1989) J. Am. Chem. Soc. 111, 7232-7239], reaction of aflatoxin B1 8,9-epoxide with d(ATGCAT)2 exhibits a limiting stoichiometry of 2:1 aflatoxin B1:d(ATGCAT)2. 1H NOE experiments, nonselective 1H T1 relaxation measurements, and 1H chemical shift perturbations demonstrate that in both modified oligodeoxynucleotides the aflatoxin moiety is intercalated above the 5'-face of the modified guanine. The oligodeoxynucleotides remain right-handed, and perturbation of the B-DNA structure is localized adjacent to the adducted guanine. Aflatoxin-oligodeoxynucleotide 1H NOEs are observed between aflatoxin and the 5'-neighbor base pair and include both the major groove and the minor groove. The aflatoxin methoxy and cyclopentenone ring protons face into the mino...Continue Reading

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Citations

Sep 14, 2002·Biopolymers·Indrajit Giri, Michael P Stone
Jul 24, 1998·Mutation Research·F P GuengerichS Langouët
Mar 5, 1999·Mutation Research·J S Wang, J D Groopman
Sep 3, 2003·Bioorganic & Medicinal Chemistry Letters·Kazunobu ToshimaShuichi Matsumura
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Feb 20, 1996·Proceedings of the National Academy of Sciences of the United States of America·E A BaileyJ M Essigmann
Feb 21, 2008·Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment·T D PhillipsJ-S Wang
Oct 26, 2013·Journal of Toxicology and Environmental Health. Part a·Susana ViegasCarla Viegas
May 16, 2002·Proceedings of the National Academy of Sciences of the United States of America·Maryann E SmelaJohn M Essigmann
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Feb 20, 2002·Chemical Reviews·Robert E. Minto, Craig A. Townsend

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