Synthesis of oligonucleotides containing the N2-deoxyguanosine adduct of the dietary carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline.

Stover JS, Rizzo CJ
Chem Res Toxicol. 2007 20 (12): 1972-9

PMID: 17914884 · PMCID: PMC3138521 · DOI:10.1021/tx7002867

2-amino-3-methylimidazo[4,5-f]quinoline (IQ) is a highly mutagenic heterocyclic amine formed in all cooked meats. IQ has been found to be a potent inducer of frameshift mutations in bacteria and carcinogenic in laboratory animals. Upon metabolic activation, IQ forms covalent adducts at the C8- and N2-positions of deoxyguanosine with a relative ratio of up to approximately 4:1. We have previously incorporated the major dGuo-C8-IQ adduct into oligonucleotides through the corresponding phosphoramidite reagent. We report here the sequence-specific synthesis of oligonucleotides containing the minor dGuo-N2-IQ adduct. Thermal melting analysis revealed that the dGuo-N2-IQ adduct significantly destabilizes duplex DNA.

MeSH Terms (7)

Carcinogens Circular Dichroism Deoxyguanosine Electrophoresis, Capillary Oligonucleotides Organophosphorus Compounds Quinolines

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