Synthesis and characterization of oligonucleotides containing a nitrogen mustard formamidopyrimidine monoadduct of deoxyguanosine.

Christov PP, Son KJ, Rizzo CJ
Chem Res Toxicol. 2014 27 (9): 1610-8

PMID: 25136769 · PMCID: PMC4164228 · DOI:10.1021/tx5002354

N(5)-Substituted formamidopyrimidine adducts have been observed from the reaction of dGuo or DNA with aziridine containing electrophiles, including nitrogen mustards. However, the role of substituted Fapy-dGuo adducts in the biological response to nitrogen mustards and related species has not been extensively explored. We have developed chemistry for the site-specific synthesis of oligonucleotides containing an N(5)-nitrogen mustard Fapy-dGuo using the phosphoramidite approach. The lesion was found to be a good substrate for Escherichia coli endonuclease IV and formamidopyrimidine glycosylase.

MeSH Terms (14)

Base Sequence Deoxyguanosine Deoxyribonuclease IV (Phage T4-Induced) DNA-Formamidopyrimidine Glycosylase DNA Adducts DNA Repair Electrophoresis, Agar Gel Escherichia coli Escherichia coli Proteins Kinetics Mechlorethamine Oligonucleotides Organophosphorus Compounds Pyrimidines

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