Production of methylguanidine from creatinine via creatol by active oxygen species: analyses of the catabolism in vitro.
The chemical oxidative conversion of creatinine (Cr) into methylguanidine (MG) has been followed by 1H-NMR and HPLC. By using active oxygen species generated by Fenton's reagent (Fe2+ and H2O2) or the similar reagent (Fe3+ and H2O2), creatol (CTL), a metabolite newly isolated from the urine of uremic patients, and creatones A and B were experimentally detected in the reaction mixture and implicated as successive intermediates in the pathway from CR to MG. An alternative oxidation of Cr to demethylcreatinine (glycocyamidine) was also observed. The importance of CTL in this in vitro oxidation mechanism is discussed.
Nakamura
K
K
Department of Natural Products Chemistry, Institute of Bio-Active Science (IBAS), Nippon Zoki Pharmaceutical Co. Ltd., Hyogo, Japan.
Ienaga
K
K
Yokozawa
T
T
Fujitsuka
N
N
Oura
H
H
D002851:Chromatography, High Pressure Liquid; D003404:Creatinine / Q000031:analogs & derivatives* / Q000378:metabolism*; D016166:Free Radical Scavengers; D005609:Free Radicals; D006861:Hydrogen Peroxide; D006868:Hydrolysis; D006878:Hydroxides; D017665:Hydroxyl Radical; D007501:Iron; D009682:Magnetic Resonance Spectroscopy; D008760:Methylguanidine / Q000378:metabolism*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010100:Oxygen / Q000378:metabolism*
D016166:Free Radical Scavengers; D005609:Free Radicals; D006878:Hydroxides; C064402:creatol; D017665:Hydroxyl Radical; D008760:Methylguanidine; D003404:Creatinine; D006861:Hydrogen Peroxide; D007501:Iron; D010100:Oxygen