This review is the fourth update of the original review, published in 1999, on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2006. The review covers fundamental studies, fragmentation of carbohydrate ions, method developments, and applications of the technique to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, glycated proteins, glycolipids from bacteria, glycosides, and various other natural products. There is a short section on the use of MALDI-TOF mass spectrometry for the study of enzymes involved in glycan processing, a section on industrial processes, particularly the development of biopharmaceuticals and a section on the use of MALDI–MS to monitor products of chemical synthesis of carbohydrates. Large carbohydrate–protein complexes and glycodendrimers are highlighted in this final section. © 2010 Wiley Periodicals, Inc., Mass Spec Rev 30:1–100, 2011

Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: an update for the period 2005-2006.

Non-enzymatic modification of proteins by carbohydrates, known as glycation, leads to generation of advanced glycation end-products (AGEs). In our study we used in vitro generated AGEs to model glycation in vivo. We discovered in vivo analogs of unusual melibiose-adducts designated MAGEs (mel-derived AGEs) synthesized in vitro under anhydrous conditions with bovine serum albumin and myoglobin. Using nuclear magnetic resonance spectroscopy we have identified MAGEs as a set of isomers, with open-chain and cyclic structures, of the fructosamine moiety. We generated a mouse anti-MAGE monoclonal antibody and show for the first time that the native and previously undescribed analogous glycation product exists in living organisms and is naturally present in tissues of both invertebrates and vertebrates, including humans. We also report MAGE cross-reactive auto-antibodies in patients with diabetes. We anticipate our approach for modeling glycation in vivo will be a foundational methodology in cell biology. Further studies relevant to the discovery of MAGE may contribute to clarifying disease mechanisms and to the development of novel therapeutic options for diabetic complications, neuropathology, and cancer.

/pdf/the-melibiose-derived-glycation-product-mimics-a-unique-2vhbom0c3b.pdf

The melibiose-derived glycation product mimics a unique epitope present in human and animal tissues

Introduction:
The transfusion of packed red blood cells (PRBCs) is a significant risk to blood recipients. Blood banking procedures permit the storage of PRBCs for up to 42 days. Storage of PRBCs can cause polymorphonuclear granulocytes (PMNs) activation and the development of neutrophil-mediated transfusion-related acute lung injury. The aim of our study was to determine if PRBC storage has an influence on the formation of arachidonic acid (AA) and advanced glycation end products (AGEs).

The effect of packed red blood cell storage on arachidonic acid and advanced glycation end-product formation.

The most abundant proteins in the arteries are those of extracellular matrix, ie. collagen and elastin. Due to their long half-lifes these proteins have an increased chance to undergo glycation. The aim of this study was to determine relationship between the content of the main extracellular matrix proteins and the advanced glycation end products (AGEs) in arteries. In this study 103 fragments of aorta were analyzed by ELISA and immunobloting for the content of collagens type I, III and IV and elastin and the content of advanced glycation end-products (AGE). A negative correlation between the content of collagens type III and IV and AGE (r = −0,258, p = 0,0122, and a weak negative correlation between collagen type III and age of the sample donor (r = 0,218, p = 0,0262) were demonstrated. This result comes as a surprise and it contradicts an intuitive assumption that with more glycation substrate, i.e. matrix proteins, more AGE products are expected. We have concluded that the results of the ELISA tests must have been influenced by the glycation. As a consequence, either modified protein molecules were not being recognized by the antibodies, or the glycation, and formation of crosslinks have blocked access of the antibodies to the antigen. It will conceal the effect of the linear dependence between the result (absorbance/densitometry) from the quantity of protein to which the antibody is directed.

/pdf/advanced-glycation-end-products-as-a-source-of-artifacts-in-3ky0okhipw.pdf

Advanced glycation end products as a source of artifacts in immunoenzymatic methods

An association between the cancer invasive activities of cells and their exposure to advanced glycation end-products (AGEs) was described early in some reports. An incubation of cells with BSA–AGE (bovine serum albumin–AGE), BSA–carboxymethyllysine and BSA–methylglyoxal (BSA–MG) resulted in a significant increase in DNA damage. We examined the genotoxic activity of new products synthesized under nonaqueous conditions. These were high molecular mass MAGEs (HMW–MAGEs) formed from protein and melibiose and low molecular mass MAGEs (LMW–MAGEs) obtained from the melibiose and N-α-acetyllysine and N-α-acetylarginine. We have observed by measuring of micronuclei in human lymphocytes in vitro that the studied HMW–MAGEs expressed the genotoxicity. The number of micronuclei (MN) in lymphocytes reached 40.22 ± 5.34 promille (MN/1000CBL), compared to 28.80 ± 6.50 MN/1000 CBL for the reference BSA–MG, whereas a control value was 20.66 ± 1.39 MN/1000CBL. However, the LMW–MAGE fractions did not induce micronuclei formation in the culture of lymphocytes and partially protected DNA against damage in the cells irradiated with X-ray. Human melanoma and all other studied cells, such as bronchial epithelial cells, lung cancer cells and colorectal cancer cells, are susceptible to the genotoxic effects of HMW–MAGEs. The LMW–MAGEs are not genotoxic, while they inhibit HMW–MAGE genotoxic activity. With regard to apoptosis, it is induced with the HMW–MAGE compounds, in the p53 independent way, whereas the low molecular mass product inhibits the apoptosis induction. Further investigations will potentially indicate beneficial apoptotic effect on cancer cells.

https://www.mdpi.com/2073-4425/12/5/729/pdf

The Genotoxic and Pro-Apoptotic Activities of Advanced Glycation End-Products (MAGE) Measured with Micronuclei Assay Are Inhibited by Their Low Molecular Mass Counterparts.

Introduction Advanced glycation end-products play an important role in diseases related to diabetes and aging processes. Model compounds are synthesized in order to prepare the diagnostic and experimental tools for studying the mechanisms of pathogenesis. The objective of the present study was to accelerate glycation and upgrade its efficiency under high-pressure conditions. Material/methods Aqueous solutions of proteins were kept with carbohydrates under a pressure of up to 850 MPa for several hours. Then the high-pressure glycation (HPG) products were fractionated on a Sephadex G-200 column and characterized with SDS-PAGE and MALDI-TOF mass spectrometry. Results The low-molecular-mass fraction of glycated proteins was separated from the two fractions containing high-and intermediate-molecular-mass cross-linked products of glycation. The products were then compared with those obtained with the high-temperature glycation (HTG) procedure carried out in dry conditions with a lyophilized mixture of substrates. The fractionated products were used to prepare rabbit sera. Conclusions The immunoblotting experiments showed that the epitopes on the cross-linked glycation products formed in solution under high pressure differed from those originating in dry conditions at high temperature. Sera against the HPG products were specific to homologous material and did not interact with the fractions obtained by HTG. The antibodies against HTG products recognized HTG but not HPG products.

Advanced glycation end-products prepared in solution under high pressure contain epitopes distinct from those formed in the dry reaction at high temperature.

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Advanced glycation end-products prepared in solution under high pressure contain epitopes distinct from those formed in the dry reaction at high temperature.