Detection of dideoxyosone intermediates of glycation using a monoclonal antibody: Characterization of major epitope structures

Puttaiah, Shivaprakash; Zhang, Yuming; Pilch, Heather A.; Pfahler, Christoph; Oya‐Ito, Tomoko; Sayre, Lawrence M.; Nagaraj, Ram H.

doi:10.1016/j.abb.2005.12.002

Cited by 9 publications

(4 citation statements)

References 26 publications

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“…Addition of 500 or 1000 µM 1,2-diaminobenzene, a powerful dicarbonyl trapping agent [31], almost completely inhibited pentosidine formation from Amadori-HLP (Fig. 4C).…”

Section: Resultsmentioning

confidence: 99%

Modulation of advanced glycation endproduct synthesis by kynurenines in human lens proteins

Nagaraj

Padmanabha

Mailankot

et al. 2010

Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics

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Human lens proteins (HLP) become chemically modified by kynurenines and advanced glycation end products (AGEs) during aging and cataractogenesis. We investigated the effects of kynurenines on AGE synthesis in HLP. We found that incubation with 5 mM ribose or 5 mM ascorbate produced significant quantities of pentosidine, and this was further enhanced in the presence of two different kynurenines (200-500 µM): N-formylkynurenine (Nfk) and kynurenine (Kyn). Another related compound, 3-hydroxykynurenine (3OH-Kyn), had disparate effects; low concentrations (10-200 µM) promoted pentosidine synthesis, but high concentrations (200-500 µM) inhibited it. 3OH-Kyn showed similar effects on pentosidine synthesis from Amadori-enriched HLP or ribated lysine. Chelex-100 treatment of phosphate buffer reduced pentosidine synthesis from Amadori-enriched HLP by ~90%, but it did not inhibit the stimulating effect of 3OH-Kyn and EDTA. 3OH-Kyn (100-500 µM) spontaneously produced copious amounts of H 2 O 2 (10-25 µM), but externally added H 2 O 2 had only a mild stimulating effect on pentosidine but had no effect on N ε -carboxymethyl lysine (CML) synthesis in HLP from ribose and ascorbate. Further, human lens epithelial cells incubated with ribose and 3OH-Kyn showed higher intracellular pentosidine than cells incubated with ribose alone. CML synthesis from glycating agents was inhibited 30 to 50% by 3OH-Kyn at concentrations of 100-500 µM. Argpyrimidine synthesis from 5 mM methylglyoxal was slightly inhibited by all kynurenines at concentrations of 100-500 µM. These results suggest that AGE synthesis in HLP is modulated by kynurenines, and such effects indicate a mode of interplay between kynurenines and carbohydrates important for AGE formation during lens aging and cataract formation.

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“…Addition of 500 or 1000 µM 1,2-diaminobenzene, a powerful dicarbonyl trapping agent [31], almost completely inhibited pentosidine formation from Amadori-HLP (Fig. 4C).…”

Section: Resultsmentioning

confidence: 99%

Modulation of advanced glycation endproduct synthesis by kynurenines in human lens proteins

Nagaraj

Padmanabha

Mailankot

et al. 2010

Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics

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“…The sample blank, control solvent and blank solvent contained all of the above reagents, except sample solvent with buffer instead of glucose in the sample blank, sample solvent instead of sample in the control solvent, and sample solvent instead of sample, buffer instead of glucose in the blank solvent. After incubating at 37°C for 7 days, the amounts of AGE products were determined by enzyme-linked immunosorbent assay (ELISA) [13]. Noncompetitive ELISA assays were performed at room temperature.…”

Section: Methodsmentioning

confidence: 99%

Extracts and compounds with anti-diabetic complications and anti-cancer activity from Castanea mollissina Blume (Chinese chestnut)

Zhang

Gao

Baba

et al. 2014

BMC Complement Altern Med

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BackgroundCastanea mollissima Blume (Chinese chestnut), as a food product is known for its various nutrients and functional values to the human health. The present study was carried out to analyze the anti-diabetic complications and anti-cancer activities of the bioactive compounds present in C. mollissima.MethodsThe kernels (CK), shells (CS) and involucres (CI) parts of C. Blume were extracted with 90% alcohol. The water suspension of these dried alcohol extracts were extracted using EtOAc and n-BuOH successively. The n-BuOH fraction of CI (CI-B) was isolated by silica gel column, Sephadex LH 20 column and preparative HPLC. The isolated compounds were identified by 1H-NMR, 13C-NMR, HMBC, HMQC and ESI-Q-TOF MS, All the fractions and compounds isolated were evaluated on human recombinant aldose reductase (HR-AR) assay, advanced glycation end products (AGEs) formation assay and human COLO 320 DM colon cancer cells inhibitory assay.ResultsCI-B was found to show a significant inhibitory effect in above biological screenings. Six flavonoids and three polyphenolic acids were obtained from CI-B. They were identified as kaempferol (1), kaempferol-3-O-[6''-O-(E)-p-coumaroyl]-β-D-glucopyranoside (2), kaempferol-3-O-[6''-O-(E)-p-coumaroyl]-β-D-galactopyranoside (3), kaempferol-3-O-[2''-O-(E)-p-coumaroyl]-β-D-glucopyranoside (4), kaempferol-3-O-[2", 6"-di-O-(E)-p-coumaroyl]-β-D-glucopyranoside (5) and kaempferol-3-O-[2", 6"-di-O-(E)-p-coumaroyl]-β-D-galactopyranoside (6), casuariin (7), casuarinin (8) and castalagin (9). Compounds 2–9 were found to show higher activity than quercetin (positive control) in the AR assay. Compounds 3–6, 8, and 9 showed stronger inhibitory effects than amino guanidine (positive control) on AGEs production. Compounds 4–6, 7, and 8 showed much higher cytotoxic activity than 5-fluorouracil (positive control) against the human COLO 320 DM colon cancer cells.ConclusionsOur results suggest that flavonoids and polyphenolic acids possesses anti-diabetes complications and anti-cancer properties, and they were presumed to be the bioactive components of Castanea mollissima Blume.Electronic supplementary materialThe online version of this article (doi:10.1186/1472-6882-14-422) contains supplementary material, which is available to authorized users.

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“…In that regard, recent studies by Nagaraj et al . showed that an antibody against OPD‐derived 2‐methylquinoxaline‐6‐carboxylate proteins reacted strongly with proteins glycated with fructose and ribose, and more weakly with those glycated with glucose or ascorbic acid, providing evidence for the existence of protein‐bound dideoxyglucosone intermediates 31 …”

Section: Approaches Toward Uncoupling Of Amadori Product‐derived Crosmentioning

confidence: 99%

The Role of the Amadori Product in the Complications of Diabetes

Monnier

Sell²,

Dai

et al. 2008

Annals of the New York Academy of Sciences

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Strong evidence has emerged in recent years in support of an association between advanced glycation and the complications of diabetes, whereby both glycoxidation products and oxoaldehydes have been implicated. In contrast, except for the fact that skin collagen-linked fructosamine (Amadori product) is a strong predictor of the risk of progression of microvascular disease in humans, Amadori products have not been associated with complications in most animal experiments. Below we develop the hypothesis that glucose-derived advanced glycation end products (AGEs), such as glucosepane, may inflict sustained damage to the extracellular matrix in diabetes and contribute to tissue stiffening and accelerated sclerosis in arteries, kidneys, and other organs as supported by immunochemical studies using a glucosepane antibody. We also hypothesize that many more structures derived from Amadori products with nucleophiles, such as primary amines and thiols, are expected. The selective prevention of Amadori-derived AGEs using deglycating enzymes would be desirable. However, x-ray diffraction studies of Amadoriase I crystals show that the active site of the enzyme is deeply embedded, explaining why this approach is unlikely to succeed in vivo. Preliminary experiments with nucleophiles show that aminoguanidine and other compounds block glucosepane in vitro.

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Detection of dideoxyosone intermediates of glycation using a monoclonal antibody: Characterization of major epitope structures

Cited by 9 publications

References 26 publications

Modulation of advanced glycation endproduct synthesis by kynurenines in human lens proteins

Modulation of advanced glycation endproduct synthesis by kynurenines in human lens proteins

Extracts and compounds with anti-diabetic complications and anti-cancer activity from Castanea mollissina Blume (Chinese chestnut)

The Role of the Amadori Product in the Complications of Diabetes

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