Synthesis and spectroscopic characterization of site-specific 2-amino-1-methyl-6-phenylimidazo

Nucleic Acids Research
K BrownK W Turteltaub

Abstract

The aim of the present study is to determine the chemical structure and conformation of DNA adducts formed by incubation of the bioactive form of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), N-acetoxy-PhIP, with a single-stranded 11mer oligodeoxyribonucleotide. Using conditions optimized to give the C8-dG-PhIP adduct as the major product, sufficient material was synthesized for NMR solution structure determination. The NMR data indicate that in duplex DNA this adduct exists in equilibrium between two different conformational states. In the main conformer, the covalently bound PhIP molecule intercalates in the helix, whilst in the minor conformation the PhIP ligand is probably solvent exposed. In addition to the C8-dG-PhIP adduct, at least eight polar adducts are found after reaction of N-acetoxy-PhIP with the oligonucleotide. Three of these were purified for further characterization and shown to exhibit lowest energy UV absorption bands in the range 342-347 nm, confirming the presence of PhIP or PhIP derivative. Accurate mass determination of two of the polar adducts by negative ion MALDI-TOF MS revealed ions consistent with a spirobisguanidino-PhIP derivative and a ring-opened adduct. The third adduct, which has the...Continue Reading

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Citations

Mar 24, 2004·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Robert J Turesky, Paul Vouros
Jul 5, 2001·Proceedings of the National Academy of Sciences of the United States of America·K BrownM Cosman
Mar 20, 2016·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Kevin M CooperGeraldine J Cuskelly
Jun 23, 2004·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·C L ChepanoskeK H Dingley
Sep 2, 2016·Current Protocols in Nucleic Acid Chemistry·Jingshu Guo, Robert J Turesky
Jul 18, 2021·Genes and Environment : the Official Journal of the Japanese Environmental Mutagen Society·Medjda BellamriRobert J Turesky
Sep 10, 2004·Journal of the American Chemical Society·C Eric ElmquistCarmelo J Rizzo

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