Page last updated: 2024-12-07

pentosidine

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Description

Pentosidine is an advanced glycation end product (AGE) that forms when glucose reacts with lysine and arginine residues in proteins. Its synthesis involves a complex series of reactions, including Schiff base formation, Amadori rearrangement, and oxidative degradation. Pentosidine accumulates in tissues with age and in individuals with diabetes, and is associated with various pathologies, including vascular disease, diabetic nephropathy, and Alzheimer's disease. Its formation is accelerated by hyperglycemia and oxidative stress. Pentosidine has been shown to promote inflammation, oxidative stress, and cell death, contributing to the pathogenesis of these diseases. Its accumulation is also associated with impaired endothelial function and increased vascular stiffness. Studies on pentosidine aim to elucidate its role in the development of these diseases and identify potential therapeutic targets for preventing or treating them.'

pentosidine: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

pentosidine : An imidazopyridine having norleucine and ornithine residues attached via their side-chains at the 4- and 2-positions respectively. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID119593
CHEBI ID59951
SCHEMBL ID51200
MeSH IDM0172217

Synonyms (24)

Synonym
pentosidine
124505-87-9
CHEBI:59951 ,
6-(2-{[(4s)-4-amino-4-carboxybutyl]amino}-4h-imidazo[4,5-b]pyridin-4-yl)-l-norleucine
bj4i2x2cqj ,
4h-imidazo(4,5-b)pyridine-4-hexanoic acid, alpha-amino-2-((4-amino-4-carboxybutyl)amino)-, (s-(r*,r*))-
unii-bj4i2x2cqj
4h-imidazo(4,5-b)pyridine-4-hexanoic acid, alpha-amino-2-(((4s)-4-amino-4-carboxybutyl)amino)-, (alphas)-
EPITOPE ID:140093
(2s)-2-amino-6-(2-(((4s)- 4-amino-5-hydroxy-5-oxopentyl))-4-imidazo (4,5-b)pyridinyl)hexanoic acid
SCHEMBL51200
DTXSID60154417
(2s)-2-amino-6-(2-{[(4s)-4-amino-4-carboxybutyl]amino}-4h-imidazo[4,5-b]pyridin-4-yl)hexanoic acid
J-005087
(2s)-2-amino-6-[2-[[(4s)-4-amino-4-carboxybutyl]amino]imidazo[4,5-b]pyridin-4-yl]hexanoic acid
AYEKKSTZQYEZPU-RYUDHWBXSA-N
Q7165277
(s)-2-amino-6-(2-(((s)-4-amino-4-carboxybutyl)amino)-4h-imidazo[4,5-b]pyridin-4-yl)hexanoic acid
4h-imidazo[4,5-b]pyridine-4-hexanoic acid, alpha-amino-2-[[(4s)-4-amino-4-carboxybutyl]amino]-, (alphas)-
(s)-2-amino-6-(2-(((s)-4-amino-4-carboxybutyl)amino)-4h-imidazo[4,5-b]pyridin-4-yl)hexanoicacid
(alphas)-alpha-amino-2-[[(4s)-4-amino-4-carboxybutyl]amino]-4h-imidazo[4,5-b]pyridine-4-hexanoic acid
[s-(r*,r*)]-alpha-amino-2-[(4-amino-4-carboxybutyl)amino] -4h-imidazo[4,5-b]pyridine-4-hexanoic acid
CS-0059403
AKOS040754903

Research Excerpts

Overview

Pentosidine is an independent risk factor for sarcopenia in Chinese middle-aged and elderly men with type 2 diabetes mellitus. Pentosidine appears to be an indicator toward a chronic tissue stiffness leading to decreased cell number.

ExcerptReferenceRelevance
"Pentosidine (PEN) is an advanced glycation end-product (AGEs), where a fluorescent cross-link is formed between lysine and arginine residues in proteins. "( Glucuronic acid is a novel source of pentosidine, associated with schizophrenia.
Arai, M; Iino, K; Itokawa, M; Kamiguchi, H; Miyashita, M; Nagai, R; Nishida, A; Ozawa, A; Sugawa, H; Suzuki, K; Tabata, K; Toriumi, K; Usami, S; Yamaguchi, S; Yamasaki, S, 2023
)
2.63
"Pentosidine is an independent risk factor for sarcopenia in Chinese middle-aged and elderly men with type 2 diabetes mellitus. "( Elevated serum pentosidine is independently associated with the high prevalence of sarcopenia in Chinese middle-aged and elderly men with type 2 diabetes mellitus.
Du, Y; Liu, J; Lu, A; Ye, X; Zhang, Q; Zhang, X, 2021
)
2.42
"Pentosidine is an advanced glycation end product (AGE) associated with fracture in adults with diabetes. "( Pentosidine Is Associated With Cortical Bone Geometry and Insulin Resistance in Otherwise Healthy Children.
Dain, JA; Kindler, JM; Laing, EM; Lewis, RD; Liu, W, 2019
)
3.4
"Pentosidine is an advanced glycation end product (AGE). "( Association of serum pentosidine with arterial stiffness in hemodialysis patients.
Cui, T; Guo, R; Jia, H; Ma, L; Peng, L; Sun, F; Yu, Z; Zhou, Y, 2010
)
2.12
"Pentosidine appears to be an indicator toward a chronic tissue stiffness leading to decreased cell number rather than a cause of ROM restriction induced by joint immobilization."( Tissue stiffness induced by prolonged immobilization of the rat knee joint and relevance of AGEs (pentosidine).
Atomi, Y; Hatta, H; Lee, S; Ohsako, M; Sakurai, T; Saura, R, 2010
)
1.3
"Pentosidine is an advanced glycation end product, formed by oxidation and glycation that accumulates markedly during end-stage renal failure. "( The pentosidine concentration in human blood specimens is affected by heating.
Kubota, M; Nagai, R; Nakano, M; Owada, S, 2013
)
2.39
"Pentosidine is an advanced glycation end-product (AGE), formed by glycosylation and oxidation, that accumulates markedly in end-stage renal disease (ESRD). "( Plasma pentosidine is associated with inflammation and malnutrition in end-stage renal disease patients starting on dialysis therapy.
Anderstam, B; Bárány, P; Fehrman-Ekholm, I; Heimbürger, O; Lindholm, B; Pecoits-Filho, R; Qureshi, AR; Rodríguez Ayala, E; Stenvinkel, P; Suliman, ME, 2003
)
2.22
"Pentosidine (Pen) is a senescent crosslink formed between arginine and lysine in matrix proteins, including collagen."( The changes in crosslink contents in tissues after formalin fixation.
Abe, M; Horiuchi, K; Nagano, A; Takahashi, M, 2003
)
1.04
"Pentosidine is an advanced glycation end product formed by sequential glycation and oxidation. "( High levels of urinary pentosidine, an advanced glycation end product, in children with acute exacerbation of atopic dermatitis: relationship with oxidative stress.
Hiraoka, M; Ito, S; Mayumi, M; Noiri, E; Ohta, N; Sato, S; Shibata, R; Tsukahara, H, 2003
)
2.07
"Pentosidine is an advanced glycation end-product (AGE) appearing when arginine and lysine residues in proteins are cross-linked with carbonyl derivatives. "( A sensitive and specific HPLC method for the determination of total pentosidine concentration in plasma.
Bukowska, H; Chlubek, D; Ciechanowski, K; Dziedziejko, V; Safranow, K; Słowik-Zyłka, D, 2004
)
2
"Pentosidine is a fluorescent protein cross-link and glycoxidation marker for the advanced glycation reaction in diabetes, aging, and uremia. "( ELISA of pentosidine, an advanced glycation end product, in biological specimens.
Monnier, VM; Taneda, S, 1994
)
2.15
"Pentosidine is an advanced Maillard/glycation reaction product the formation of which in human skin is significantly increased in Type 1 (insulin-dependent) diabetes mellitus and correlates with the severity of diabetic complications. "( Differential effects of type 2 (non-insulin-dependent) diabetes mellitus on pentosidine formation in skin and glomerular basement membrane.
Carlson, EC; Monnier, VM; Sell, DR, 1993
)
1.96
"Pentosidine is a fluorescent cross-link compound that accumulates in human tissues from uremic and diabetic patients. "( Quantification of the cross-link pentosidine in serum from normal and uremic subjects.
Denda, M; Horiuchi, K; Inoue, T; Ishihara, C; Kawana, K; Kushida, K; Takahashi, M, 1993
)
2.01
"Pentosidine is a useful marker of advanced glycation end-products (AGE) which form cross-links between proteins and have been found elevated in plasma and tissues of uraemic and haemodialysed subjects. "( Plasma advanced glycosylation end-products in maintenance haemodialysis patients.
Cosso, L; Dapino, D; Gurreri, G; Odetti, P; Pronzato, MA, 1995
)
1.73
"Pentosidine (Pen) is a senescent crosslink and one of the advanced glycation end products."( Direct measurement of crosslinks, pyridinoline, deoxypyridinoline, and pentosidine, in the hydrolysate of tissues using high-performance liquid chromatography.
Hoshino, H; Inoue, T; Kushida, K; Takahashi, M, 1995
)
1.25
"Pentosidine is an advanced glycation end product and its formation is shown to be closely related to oxidative processes. "( Accumulation of albumin-linked and free-form pentosidine in the circulation of uremic patients with end-stage renal failure: renal implications in the pathophysiology of pentosidine.
Iida, Y; Kurokawa, K; Maeda, K; Miyata, T; Shinzato, T; Tanaka, S; Ueda, Y; van Ypersele de Strihou, C, 1996
)
2
"Pentosidine is an advanced glycation end product (AGE) formed by combined processes of glycation and oxidation (glycoxidation) between carbohydrate-derived carbonyl group and protein amino group. "( Increased pentosidine, an advanced glycation end product, in plasma and synovial fluid from patients with rheumatoid arthritis and its relation with inflammatory markers.
Ishiguro, N; Ito, T; Iwata, H; Kurokawa, K; Miyata, T; Nangaku, M; Yasuda, Y, 1998
)
2.15
"Pentosidine is an advanced glycation end product (AGE) formed during Maillard or browning reaction by non-enzymatic glycation and oxidation (glycoxidation). "( Implication of altered redox regulation by antioxidant enzymes in the increased plasma pentosidine, an advanced glycation end product, in uremia.
Hashimoto, T; Izuhara, Y; Kurokawa, K; Miyata, T; Sakai, H; Ueda, Y; Yamada, H, 1998
)
1.97
"Pentosidine is an advanced glycation endproduct (AGE) and there is evidence that shows AGEs contribute to the pathogenesis of the complications in patients undergoing HD."( The advanced glycation endproduct, pentosidine, in the carpal ligament in patients with carpal tunnel syndrome undergoing hemodialysis: comparison with idiopathic carpal tunnel syndrome.
Baba, S; Hoshino, H; Inoue, T; Kushida, K; Murata, H; Takahashi, M, 1998
)
1.3
"Pentosidine is an advanced glycation endproduct formed by glycosylation and oxidation. "( Pentosidine in synovial fluid in osteoarthritis and rheumatoid arthritis: relationship with disease activity in rheumatoid arthritis.
Chen, JR; Inoue, T; Kushida, K; Miyamoto, S; Suzuki, M; Takahashi, M, 1998
)
3.19
"Pentosidine is a well-known and characterized structure among them, and has been implicated in the pathogenesis of complications associated with chronic renal failure and long-term dialysis, such as dialysis-related amyloidosis and atherosclerosis."( A sensitive and specific ELISA for plasma pentosidine.
Asahi, K; Inagi, R; Izuhara, Y; Kurokawa, K; Miyata, T; Sakai, H; Suzuki, D; Ueda, Y, 1999
)
1.29
"Pentosidine is an advanced glycation end product. "( Effect of age and menopause on serum concentrations of pentosidine, an advanced glycation end product.
Nagano, A; Oikawa, M; Takahashi, M, 2000
)
2
"Pentosidine is a biomarker of glycoxidation reaction."( The relationship of oxidative DNA damage marker 8-hydroxydeoxyguanosine and glycoxidative damage marker pentosidine.
Fan, W; Horiuchi, K; Kouda, K; Nakamura, H; Takeuchi, H, 2001
)
1.25
"Pentosidine is an advanced glycosylation end product and protein cross-link that results from the reaction of pentoses with proteins. "( Pentosidine formation in skin correlates with severity of complications in individuals with long-standing IDDM.
Fogarty, J; Lapolla, A; Monnier, VM; Odetti, P; Sell, DR, 1992
)
3.17
"Pentosidine is a fluorescent advanced Maillard/glycosylation product and protein cross-link present in elevated amounts in skin from diabetic and uremic subjects. "( Chromatographic quantitation of plasma and erythrocyte pentosidine in diabetic and uremic subjects.
Fogarty, J; Monnier, VM; Odetti, P; Sell, DR, 1992
)
1.97
"Pentosidine is a recently discovered fluorescent protein cross-link from human extracellular matrix that involves lysyl and arginyl residues in an imidazo (4, 5b) pyridinium ring. "( Mechanism of formation of the Maillard protein cross-link pentosidine. Glucose, fructose, and ascorbate as pentosidine precursors.
Grandhee, SK; Monnier, VM, 1991
)
1.97
"Pentosidine is a recently discovered protein crosslink, involving lysine and arginine residues linked together in an imidazo [4,5,6] pyridinium ring formed by a 5-carbon sugar during nonenzymatic browning (Maillard reaction). "( High correlation between pentosidine protein crosslinks and pigmentation implicates ascorbate oxidation in human lens senescence and cataractogenesis.
Monnier, VM; Nagaraj, RH; Ortwerth, BJ; Prabhakaram, M; Sell, DR, 1991
)
2.03

Effects

Pentosidine has been described as an independent risk factor for hip and vertebral fracture in postmenopausal Japanese women. Pentosidine plasma level has been identified as a surrogate marker of carbonyl precursors.

ExcerptReferenceRelevance
"Pentosidine has a pivotal role in diabetic complications, probably as a consequence of the diverse properties of this compound, which alters the structure and function of molecules in biological systems."( [Pentosidine: a new biomarker in diabetes mellitus complications].
García-Salcedo, JA; Morales, S; Muñoz-Torres, M, 2011
)
2
"Pentosidine has been identified as a surrogate marker of bone quality."( Evaluation of Bone Turnover / Quality Markers and Bone Mineral Density in Prostate Cancer Patients Receiving Androgen Deprivation Therapy with or without Denosumab.
Ito, K; Koike, H; Matsui, H; Miyazawa, Y; Nomura, M; Sekine, Y; Shibata, Y; Suzuki, K; Syuto, T, 2017
)
1.18
"Pentosidine has been described as an independent risk factor for hip and vertebral fracture in postmenopausal Japanese women. "( Urinary levels of pentosidine and the risk of fracture in postmenopausal women: the OFELY study.
Bertholon, C; Chapurlat, R; Gineyts, E; Munoz, F; Sornay-Rendu, E, 2010
)
2.14
"Pentosidine has a pivotal role in diabetic complications, probably as a consequence of the diverse properties of this compound, which alters the structure and function of molecules in biological systems."( [Pentosidine: a new biomarker in diabetes mellitus complications].
García-Salcedo, JA; Morales, S; Muñoz-Torres, M, 2011
)
2
"Pentosidine plasma level has been identified as a surrogate marker of carbonyl precursors ("carbonyl stress")."( Influence of hemodialysis membrane type on pentosidine plasma level, a marker of "carbonyl stress".
Ishida, N; Jadoul, M; Kurokawa, K; Miyata, T; Robert, A; Saito, A; Ueda, Y; Van Ypersele De Strihou, C; Yasuda, Y, 1999
)
1.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
cross-linking reagentA reagent with two reactive groups, usually at opposite ends of the molecule, that are capable of reacting with and thereby forming bridges between macromolecules, principally side chains of amino acids in proteins, allowing the locations of naturally reactive areas within the proteins to be identified.
biomarkerA substance used as an indicator of a biological state.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
imidazopyridine
non-proteinogenic L-alpha-amino acidAny L-alpha-amino acid which is not a member of the group of 23 proteinogenic amino acids.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (559)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (0.18)18.7374
1990's138 (24.69)18.2507
2000's200 (35.78)29.6817
2010's197 (35.24)24.3611
2020's23 (4.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 34.27

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index34.27 (24.57)
Research Supply Index6.42 (2.92)
Research Growth Index6.91 (4.65)
Search Engine Demand Index45.20 (26.88)
Search Engine Supply Index2.03 (0.95)

This Compound (34.27)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials34 (5.89%)5.53%
Reviews36 (6.24%)6.00%
Case Studies4 (0.69%)4.05%
Observational5 (0.87%)0.25%
Other498 (86.31%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]