Misincorporation of 2'-deoxyoxanosine into DNA: a molecular basis for NO-induced mutagenesis derived from theoretical calculations.
A wide range of theoretical methods, including high level ab initio, density functional, self-consistent reaction field, molecular dynamics and thermodynamic integration calculations, have been used to analyze the mutagenic properties of oxanosine. The major tautomeric forms in the gas phase and aqueous solution have been determined. The ability of oxanosine to recognize thymine and cytosine in the gas phase and in the DNA environment has been compared with that of guanine. A physicochemical explanation for the mutagenic properties of oxanosine is suggested.
Hernández
B
B
Departament de Bioquímica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1, Barcelona 08028, Spain.
Soliva
R
R
Luque
F J
FJ
Orozco
M
M
D020029:Base Pairing; D001483:Base Sequence; D003198:Computer Simulation; D003596:Cytosine / Q000378:metabolism; D004247:DNA / Q000737:chemistry* / Q000235:genetics* / Q000378:metabolism; D003853:Deoxyribonucleosides / Q000737:chemistry / Q000235:genetics / Q000378:metabolism* / Q000633:toxicity; D019281:Dimerization; D006860:Hydrogen Bonding; D008958:Models, Molecular; D016296:Mutagenesis / Q000187:drug effects* / Q000235:genetics; D009153:Mutagens / Q000737:chemistry / Q000378:metabolism / Q000633:toxicity; D009569:Nitric Oxide / Q000494:pharmacology*; D018583:Pliability; D012996:Solutions; D013816:Thermodynamics; D013941:Thymine / Q000378:metabolism
D003853:Deoxyribonucleosides; D009153:Mutagens; D012996:Solutions; D009569:Nitric Oxide; C042917:2'-deoxyoxanosine; D003596:Cytosine; D004247:DNA; D013941:Thymine