Identification of Nε-(carboxyethyl)lysine, one of the methylglyoxal-derived AGE structures, in glucose-modified protein: mechanism for protein modification by reactive aldehydes

Nagai, Ryoji; Araki, Toshimitsu; Hayashi, Cristina Miki; Hayase, Fumitaka; Horiuchi, Seikoh

doi:10.1016/s1570-0232(02)01019-x

Cited by 31 publications

(18 citation statements)

References 29 publications

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“…The CML and CEL content of the samples was determined by amino acid analysis after acid hydrolysis (6 N HCl for 24 h at 110°C) using an amino acid analyzer (L-8500A, Hitachi) (Tokyo, Japan) equipped with an Mera et al,Page 7 ion exchange column (#2622 SC, 4.6 x 80 mm, Hitachi), as described previously (Matsumoto et al, 2000). Hippuryl-CML (Ikeda et al, 1996) and hippuryl-CEL (Nagai et al, 2003) were prepared as described previously.…”

Section: Preparation Of Cml-modified Hsa and Cel-modified Hsamentioning

confidence: 99%

“…Recent studies have shown that the aldehydes, glyoxal (GO) (Koito et al, 2004) and methylglyoxal (MG) (Nagai et al, 2003), react with lysine to form CML and CEL, respectively. Based on this knowledge, we tested the ability of 2G11 to distinguish between GO and MG modified HSA by non-competitive ELISA.…”

Section: Immunoreactivity Of the Monoclonal Anti-cml Antibodymentioning

confidence: 99%

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Glutaraldehyde is an effective cross-linker for production of antibodies against advanced glycation end-products

Mera

Nagai

Brock

et al. 2008

Journal of Immunological Methods

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Section: Preparation Of Cml-modified Hsa and Cel-modified Hsamentioning

confidence: 99%

Section: Immunoreactivity Of the Monoclonal Anti-cml Antibodymentioning

confidence: 99%

Glutaraldehyde is an effective cross-linker for production of antibodies against advanced glycation end-products

Mera

Nagai

Brock

et al. 2008

Journal of Immunological Methods

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“…immunoassay or fluorescence measurement, reflect group reactivity and are not specific for chemically well-defined substances. Previously, CML, CEL and related compounds have been determined by immunoassay (Schleicher et al, 1997), high-pressure liquid chromatography (HPLC; Friess et al, 2003;Nagai et al, 2003), tandem mass spectrometry (Thornalley et al, 2003) and selected ion monitoring gas chromatography/mass spectrometry (SIM-GC/MS; Ahmed et al, 1997). CML has been quantified in hydrolyzed sample of human skin Dyer et al, 1993), lens (Dunn et al, 1989), in rat (Liardon et al, 1987) and human urine (Knecht et al, 1991).…”

Section: Introductionmentioning

confidence: 99%

Rapid and simple method for determination of Nɛ-(carboxymethyl)lysine and Nɛ-(carboxyethyl)lysine in urine using gas chromatography[sol ]mass spectrometry

Petrovič¹,

Futas²,

Chandoga³

et al. 2005

Biomed. Chromatogr.

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A new procedure was developed to determine in urine the concentrations of N(epsilon)-(carboxymethyl)lysine (CML) and N(epsilon)-(carboxyethyl)lysine (CEL), the major products of oxidative modification of glycated proteins, to assess levels of oxidative stress in physiological systems. The urine samples were acetonitrile-deproteinized, then derivatized by ethylchloroformate, and N(O,S)-ethoxycarbonyl ethyl esters of amino acids were analysed by isotope dilution gas chromatography/mass spectrometry. Recovery averaged 89%. Linearity was excellent (r = 0.998-0.999) in the 0.5-25 micromol/L range for CML and CEL. The limit of detection of this assay was 0.1 micromol/L (corresponding to 0.20 pmol of CML or CEL on column). Intra-day and inter-day precisions were likewise excellent, with relative standard deviations <4.63 and <6.15%, respectively. Accuracy of CML and CEL determination (15 micromol/L) was 2.9 and 5.9% of the estimated theoretical value. The time from obtaining the urine sample to determination of the concentration from the chromatographic peak was 80 min or less. This method is sensitive, reproducible, accurate, relatively cheap and very simple. It can be useful for laboratories involved in the diagnosis and monitoring of age-related chronic diseases.

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“…CML and CEL have been analyzed by cation-exchange chromatography with postcolumn ninhydrin derivatization (8 ) and CML by reversed-phase HPLC with fluorescence detection after precolumn derivatization with ophthaldialdehyde reagent (9 ). 6-Aminoquinolyl-Nhydroxysuccinimidyl-carbamate, a derivatization reagent that yields more stable derivatives, has been used for the analysis of early glycation products and AGEs, including CML and CEL, in human serum albumin (10,11 ).…”

mentioning

confidence: 99%

Measurement of Nε-(Carboxymethyl)lysine and Nε-(Carboxyethyl)lysine in Human Plasma Protein by Stable-Isotope-Dilution Tandem Mass Spectrometry

Teerlink

Barto²,

Brink³

et al. 2004

Clinical Chemistry

117

104

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Results: CML and CEL were separated with baseline resolution with a total analysis time of 21 min. The lower limit of quantification was 0.02 mol/L for both compounds. Mean recoveries from plasma samples to which CML and CEL had been added were 92% for CML and 98% for CEL. Within-day CVs were <7.2% for CML and <8.2% for CEL, and between-day CVs were <8.5% for CML and <9.0% for CEL. In healthy individuals (n ‫؍‬ 10), mean (SD) plasma concentrations of CML and CEL were 2.80 (0.40) mol/L (range, 2.1-3.4 mol/L) and 0.82 (0.21) mol/L (range, 0.5-1.2 mol/L), respectively. In hemodialysis (n ‫؍‬ 17) and peritoneal dialysis (n ‫؍‬ 9) patients, plasma concentrations of CML and CEL were increased two-to threefold compared with controls, with-

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Identification of Nε-(carboxyethyl)lysine, one of the methylglyoxal-derived AGE structures, in glucose-modified protein: mechanism for protein modification by reactive aldehydes

Cited by 31 publications

References 29 publications

Glutaraldehyde is an effective cross-linker for production of antibodies against advanced glycation end-products

Glutaraldehyde is an effective cross-linker for production of antibodies against advanced glycation end-products

Rapid and simple method for determination of Nɛ-(carboxymethyl)lysine and Nɛ-(carboxyethyl)lysine in urine using gas chromatography[sol ]mass spectrometry

Measurement of Nε-(Carboxymethyl)lysine and Nε-(Carboxyethyl)lysine in Human Plasma Protein by Stable-Isotope-Dilution Tandem Mass Spectrometry

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