Interaction of mutagenic tryptophan pyrolysate with d(CGATCG)2: intercalation model based on NMR experiments.
The solution structure of the complex of 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1), a potent mutacarcinogen isolated from tryptophan pyrolysate, with the hexamer duplex d(CGATCG)2, was analysed by 1H-NMR spectroscopy and molecular dynamic calculation. Trp-P-1 was intercalated between the CpG base pairings in a suitable manner to form the guanosine-Trp-P-1 adduct which corresponds to the major reactant of Trp-P-1 with DNA.
Mihara
Y
Y
Osaka University of Pharmaceutical Sciences, Osaka, Japan.
Doi
M
M
Inohara
T
T
Kawamura
M
M
Hamanaka
N
N
Ishida
T
T
D001482:Base Composition; D002243:Carbolines / Q000737:chemistry* / Q000378:metabolism*; D004247:DNA / Q000378:metabolism; D006151:Guanosine / Q000378:metabolism; D006571:Heterocyclic Compounds / Q000378:metabolism; D007364:Intercalating Agents / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D009153:Mutagens / Q000737:chemistry / Q000378:metabolism*; D009838:Oligodeoxyribonucleotides / Q000737:chemistry* / Q000378:metabolism*; D011084:Polycyclic Aromatic Hydrocarbons / Q000378:metabolism
D002243:Carbolines; D006571:Heterocyclic Compounds; D007364:Intercalating Agents; D009153:Mutagens; D009838:Oligodeoxyribonucleotides; D011084:Polycyclic Aromatic Hydrocarbons; D006151:Guanosine; C019133:3-amino-1-methyl-5H-pyrido(4,3-b)indole; D004247:DNA