Selective radiation-induced generation of 2-deoxyribonolactone lesions in DNA mediated by aromatic iodonium derivatives.
2-Deoxyribonolactone lesions were identified as major products of radiation damage to DNA mediated by o,o'-diphenyleneiodonium cations in a hydroxyl radical-scavenging environment. The highest selectivity toward deoxyribonolactone formation (up to 86% of all sugar-phosphate damages) and the overall reaction efficiency (up to 40% of all radiation-generated intermediates converted into products) was displayed by derivatives with positively charged (2-aminoethylthio)acetylamino and (2-aminoethylamino)acetylamino side chains. The reaction can be useful for random single-step incorporation of deoxyribonolactone lesions into single- and double-stranded oligonucleotides and highly polymerized DNA directly in commonly used buffers (PBS, phosphate, Tris-HCl, etc.) at room temperature. In combination with HPLC separation, this technique can serve as a source of short (<6 mer) sequences containing deoxyribonolactone lesions at known positions.
Roginskaya
Marina
M
Department of Physics and Astronomy, East Tennessee State University, Johnson City, Tennessee 37614, USA.
Razskazovskiy
Yuriy
Y
D000818:Animals; D001483:Base Sequence; D002021:Buffers; D002417:Cattle; D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000235:genetics* / Q000378:metabolism*; D004249:DNA Damage; D004307:Dose-Response Relationship, Radiation; D009838:Oligodeoxyribonucleotides / Q000235:genetics / Q000378:metabolism; D009861:Onium Compounds / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D010084:Oxidation-Reduction; D011830:Radiation Effects; D013379:Substrate Specificity; D013400:Sugar Acids / Q000378:metabolism*
D002021:Buffers; D009838:Oligodeoxyribonucleotides; D009861:Onium Compounds; D013400:Sugar Acids; C056405:2,4,5-trihydroxypentanoic acid gamma-lactone; C007517:diphenyleneiodonium; D004247:DNA; C427203:calf thymus DNA