Production of hydroxyl radicals and alpha-dicarbonyl compounds associated with Amadori compound-Cu2+ complex degradation.
The chemical properties of Amadori compounds in the presence of transition metal ions were studied, using the analogs 1-deoxy-1-n-butylamino-D-fructose (DBF) and N(alpha)-formyl-fructoselysine (fFL). The following characteristics were revealed: (a) DBF combined easily with Cu2+ (but no other transition metal ions) to form a DBF-Cu2+ complex in phosphate buffer, pH 7.4; (b) the complex was unstable, and degraded with the release of Cu+ during incubation at 37 degrees C; (c) degradation of the complex was associated with the production of hydroxyl radicals by the Fenton reaction and alpha-dicarbonyl compounds by non-autoxidative degradation; and (d) properties of DBF were similar to those of fFL. The above properties were additionally observed in glycated poly-Lys (GPL). Our findings indicate a novel mechanism for the generation of hydroxyl radicals and a-dicarbonyl compounds from Amadori adducts in the presence of Cu2+.
Horikawa
Hiroaki
H
Department of Chemistry, Tokyo Women's Medical University, School of Medicine, 8-1 Kawadacho, Shinjuku-ku, Tokyo 162-8666, Japan. horikawa@research.twmu.ac.jp
Okada
Midori
M
Nakamura
Yuko
Y
Sato
Azusa
A
Iwamoto
Noriko
N
D002374:Catalase / Q000494:pharmacology; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002851:Chromatography, High Pressure Liquid; D003300:Copper / Q000737:chemistry*; D004492:Edetic Acid / Q000494:pharmacology; D004578:Electron Spin Resonance Spectroscopy; D005632:Fructose / Q000031:analogs & derivatives / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D017665:Hydroxyl Radical / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008239:Lysine / Q000031:analogs & derivatives / Q000737:chemistry*; D012996:Solutions
C472991:1-deoxy-1-n-butylaminofructose; D007659:Ketones; C472992:N(alpha)-formyl-fructoselysine; D012996:Solutions; D005632:Fructose; D017665:Hydroxyl Radical; D003300:Copper; D004492:Edetic Acid; D002374:Catalase; D008239:Lysine