Extending the Spectrum of α-Dicarbonyl Compounds in Vivo

Henning, Christian; Liehr, Kristin; Girndt, Matthias; Ulrich, Christof; Glomb, Marcus A.

doi:10.1074/jbc.m114.563593

Cited by 90 publications

(127 citation statements)

References 68 publications

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“…However, derivatization of α-DCs with o-phenylenediamine (OPD) to yield the corresponding quinoxalines has evolved as the most accepted procedure [14]. Furthermore, sample collection and sample preparation were found to have a major impact on the results and have to be strictly controlled [12,[15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Pathways of the Maillard reaction under physiological conditions

2016

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Initially investigated as a color formation process in thermally treated foods, nowadays, the relevance of the Maillard reaction in vivo is generally accepted. Many chronic and age-related diseases such as diabetes, uremia, atherosclerosis, cataractogenesis and Alzheimer's disease are associated with Maillard derived advanced glycation endproducts (AGEs) and α-dicarbonyl compounds as their most important precursors in terms of reactivity and abundance. However, the situation in vivo is very challenging, because Maillard chemistry is paralleled by enzymatic reactions which can lead to both, increases and decreases in certain AGEs. In addition, mechanistic findings established under the harsh conditions of food processing might not be valid under physiological conditions. The present review critically discusses the relevant α-dicarbonyl compounds as central intermediates of AGE formation in vivo with a special focus on fragmentation pathways leading to formation of amide-AGEs.

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Section: Introductionmentioning

confidence: 99%

Pathways of the Maillard reaction under physiological conditions

2016

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“…We did not distinguish between the free and reversibly bound ascorbate degradation products in our assay, unlike in a previous study (16). For DHA-Q, two derivatives were detected, as observed by Henning et al (29). Therefore, DHA-Q levels are presented as the sum of those two derivatives.…”

Section: Resultsmentioning

confidence: 81%

“…3-Hydroxykynurenine glucoside (3OHKynG) was synthesized as described previously (28). The quinoxalines of DHA and 2,3-DKG were prepared as described previously (16,29).…”

Section: Methodsmentioning

confidence: 99%

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Identification of Kynoxazine, a Novel Fluorescent Product of the Reaction between 3-Hydroxykynurenine and Erythrulose in the Human Lens, and Its Role in Protein Modification

Rakete

Nagaraj

2016

Journal of Biological Chemistry

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Kynurenine pathway metabolites and ascorbate degradation products are present in human lenses. In this study, we showed that erythrulose, a major ascorbate degradation product, reacts spontaneously with 3-hydroxykynurenine to form a fluorescent product. Structural characterization of the product revealed it to be 2-amino-4-(2-hydroxy-3-(2-hydroxyethyl)-2H-benzo[b][1, 4]oxazin-5-yl)-4-oxobutanoic acid, which we named kynoxazine. Unlike 3-hydroxykynurenine, 3-hydroxykynurenine glucoside and kynurenine were unable to form a kynoxazine-like compound, which suggested that the aminophenol moiety in 3-hydroxykynurenine is essential for the formation of kynoxazine. This reasoning was confirmed using a model compound, 1-(2-amino-3-hydroxyphenyl)ethan-1-one, which is an aminophenol lacking the amino acid moiety of 3-hydroxykynurenine. Ultra-performance liquid chromatography-tandem mass spectrometry analyses showed that kynoxazine is present in the human lens at levels ranging from 0 to 64 pmol/mg lens. Kynoxazine as well as erythrulose degraded under physiological conditions to generate 3-deoxythreosone, which modified and cross-linked proteins through the formation of an arginine adduct, 3-deoxythreosone-derived hydroimidazolone, and a lysine-arginine cross-linking adduct, 3-deoxythreosone-derived hydroimidazolimine cross-link. Ultra-performance liquid chromatography-tandem mass spectrometry quantification showed that 32-169 pmol/mg protein of 3-deoxythreosone-derived hydroimidazolone and 1.1-11.2 pmol/mg protein of 3-deoxythreosone-derived hydroimidazolimine cross-link occurred in aging lenses. Taken together, these results demonstrate a novel biochemical mechanism by which ascorbate oxidation and the kynurenine pathway intertwine, which could promote protein modification and cross-linking in aging human lenses.

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“…This compound was easily synthesized through a one pot procedure, starting from initial oxidation of L-ascorbic acid into dehydroascorbic acid followed by its reaction with o-phenylenediamine. 33,37 Our previous work showed that AAQX selectively interacts with Cu 2+ in methanolic solution, and this reaction was able to be followed through naked-eye and UV-Vis analyses. 33 On the other hand, AAQX is a polyfunctionalized molecule containing alcohol, amine, amide and quinoxaline moieties, which are able to interact with available hydroxyl groups of the cellulose fibers contained in paper via hydrogen bonds, and this fact opened a possibility for immobilizing AAQX on a paper support in attempt to develop a disposable sensor.…”

Section: Synthesis and Copper Ion Screeningmentioning

confidence: 99%

A Low-Cost Video-Based Reflectometer for Selective Detection of Cu2+ Using Paper-Based Colorimetric Sensors

Morais

Silva

Pinheiro

et al. 2017

J. Braz. Chem. Soc.

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This paper presents a low-cost reflectometer for selective detection of Cu 2+ . The reflectometer is based on an emission light source using five light-emitting diodes at different wavelengths and a detector using a webcam. The samples were prepared using a filter paper-based colorimetric sensor with ascorbic acid-based quinoxaline derivative. Video analysis using gray color intensity was used to perform both copper ion screening ( ) and quantification of Cu 2+ in spiked samples. In addition, a multivariate validation was performed. The system proved to be selective to Cu 2+ among the screened ions, and its quantification was performed using partial least square regressions. Good linearity (R 2 = 0.979, coefficient of determination), low root-mean-square error of prediction (RMSEP = 5.20 × 10 -3 mol L -1 ) and high recovery (93.39-128.64%) were achieved. This method has potential to be employed for rapid and selective determination of Cu 2+ in water using low-cost instrumentation.

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Extending the Spectrum of α-Dicarbonyl Compounds in Vivo

Cited by 90 publications

References 68 publications

Pathways of the Maillard reaction under physiological conditions

Pathways of the Maillard reaction under physiological conditions

Identification of Kynoxazine, a Novel Fluorescent Product of the Reaction between 3-Hydroxykynurenine and Erythrulose in the Human Lens, and Its Role in Protein Modification

A Low-Cost Video-Based Reflectometer for Selective Detection of Cu2+ Using Paper-Based Colorimetric Sensors

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