Formation of pentosidine during nonenzymatic browning of proteins by glucose. Identification of glucose and other carbohydrates as possible precursors of pentosidine in vivo

An Inducible Model for Unraveling the Effects of Advanced Glycation End-Product Accumulation in Aging Connective Tissues

“…Pentosidine is formed from sugars reacting with lysine and arginine residues of proteins. 62,64,82,84 As discussed previously, while photo-initiated riboflavin can react with lysine and arginine, these amino acids play a minor role in riboflavin-initiated crosslinking 83 and thus it makes sense riboflavin-465 nm would not favor the formation of pentosidine at day 0. Further, pentosidine crosslinks take longer to form than many other AGEs, 64,82,84 thus it would not be expected to form after 1 hour of treatment, as is also observed in the ribose constructs.…”

“…62,64,82,84 As discussed previously, while photo-initiated riboflavin can react with lysine and arginine, these amino acids play a minor role in riboflavin-initiated crosslinking 83 and thus it makes sense riboflavin-465 nm would not favor the formation of pentosidine at day 0. Further, pentosidine crosslinks take longer to form than many other AGEs, 64,82,84 thus it would not be expected to form after 1 hour of treatment, as is also observed in the ribose constructs. Originally, pentosidine was hypothesized to form by reaction of pentose sugars only; 62 however later studies demonstrated glucose, fructose, ascorbate, tetrose, triose, and other glycated proteins were also possible precursors with longer incubations.…”

“…Originally, pentosidine was hypothesized to form by reaction of pentose sugars only; 62 however later studies demonstrated glucose, fructose, ascorbate, tetrose, triose, and other glycated proteins were also possible precursors with longer incubations. 64,82,84 While pentoses are the most efficient source of pentosidine, these other sugars and glycated proteins can form pentosidine but at slower rates. 82,84 Thus while riboflavin-465 nm treatment does not appear to significantly form pentosidine at initiation, it is possible it could eventually lead to pentosidine formation, as is seen with 0.75 mM riboflavin-465 nm constructs having a significant increase in pentosidine fluorescence by 15 days, albeit at a much lower concentration than that induced by ribose.…”

“…64,82,84 While pentoses are the most efficient source of pentosidine, these other sugars and glycated proteins can form pentosidine but at slower rates. 82,84 Thus while riboflavin-465 nm treatment does not appear to significantly form pentosidine at initiation, it is possible it could eventually lead to pentosidine formation, as is seen with 0.75 mM riboflavin-465 nm constructs having a significant increase in pentosidine fluorescence by 15 days, albeit at a much lower concentration than that induced by ribose. Collectively, this data suggests that these two glycation systems can induce different types of AGE crosslinks and opens the door to exploring effects of tissue specific crosslink effects throughout the body.…”

Plasma pentosidine: a potential biomarker in the management of multiple sclerosis

“…Pentosidine is unique among AGEs in many ways: while other well-characterized AGEs such as N-epsilon-(carboxymethyl)lysine (CML) and N-epsilon-(carboxyethyl)lysine (CEL) originate from oxidation of both lipids and carbohydrates, 5 pentosidine originates from sequential glycation and oxidation reactions between lysine and arginine, with carbohydrate and their precursors (glucose, ribose, ascorbic acid, and 3-deoxyglucosone). 6,7…”