title: Sunlight induces N epsilon-(carboxymethyl)lysine formation from glycated polylysine-iron(III) complex.
abstract: Sunlight was found to strongly induce the formation of N epsilon-(carboxymethyl)lysine (CML) from glycated polylysine in the presence of Fe(III) ion. The initial step of this Fe(III)-catalyzed CML formation was noted to be similar to that of blueprint photography as was confirmed by the production of Turnbull's blue in sunlight-exposed glycated human serum albumin ferricyanide solution in the presence of Fe(III). Based on this, photoinduced oxidative C-C bond cleavage of the Amadori compound was assumed to be initiated by photochemical single electron transfer front ligand to Fe(III) in the Fe(III)-Amadori compound complex affording the Fe(II)-Amadori compound radical intermediate, which eventually yields either CML or active oxygen species. CML is thus a useful oxidative stress marker. The mechanism proposed here would explain the high accumulation of CML in lens protein and skin actinic elastosis.
authors.affiliation: School of Pharmacy, Tokyo University of Pharmacy and Life Science, Hachioji, Tokyo 192-0392, Japan. sakurait@ps.toyaku.ac.jp
authors.forename: T
authors.initials: T
authors.lastname: Sakurai
authors.forename: K
authors.initials: K
authors.lastname: Fujimori
authors.forename: T
authors.initials: T
authors.lastname: Ueda
authors.forename: H
authors.initials: H
authors.lastname: Shindo
authors.forename: Y
authors.initials: Y
authors.lastname: Shibusawa
authors.forename: M
authors.initials: M
authors.lastname: Nakano
mesh_terms: D017127:Glycation End Products, Advanced; D006031:Glycosylation; D006801:Humans; D066298:In Vitro Techniques; D007501:Iron / Q000737:chemistry / Q000528:radiation effects; D008239:Lysine / Q000031:analogs & derivatives* / Q000528:radiation effects*; D009682:Magnetic Resonance Spectroscopy; D010777:Photochemistry; D011107:Polylysine / Q000737:chemistry / Q000528:radiation effects; D012709:Serum Albumin / Q000528:radiation effects; D013472:Sunlight / Q000009:adverse effects*; D000093423:Glycated Serum Albumin
chemical_list: D017127:Glycation End Products, Advanced; D012709:Serum Albumin; D011107:Polylysine; C048496:N(6)-carboxymethyllysine; D007501:Iron; D008239:Lysine; D000093423:Glycated Serum Albumin