glucosepane

Description

glucosepane: a protein cross-link; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	135565852
SCHEMBL ID	22559684
MeSH ID	M0538476

Synonyms (8)

Synonym
glucosepane
(2s)-2-amino-6-((6r,7s)-2-(((s)-4-amino-4-carboxybutyl)amino)-6,7-dihydroxy-6,7,8,8a-tetrahydroimidazo(4,5-b)azepin-4(5h)-yl)hexanoic acid
glucosepan
257290-23-6
66K23JT22H ,
unii-66k23jt22h
DTXSID80894863
SCHEMBL22559684

Research Excerpts

Overview

Glucosepane is a novel AGE marker of diabetic complications that is robustly associated with nephropathic, retinopathic and neuropathic outcomes. It could be one mediator of these complications with possible diagnostic implications.

Excerpt	Reference
"Glucosepane is a structurally complex protein posttranslational modification that is believed to exist in all living organisms. "	( Concise total synthesis of glucosepane. Draghici, C; Spiegel, DA; Wang, T, 2015)
"Glucosepane is a collagen cross-linking advanced glycation end product; the structural and mechanical effects of glucosepane are still the subjects of much debate."	( Computational study of glucosepane-water and hydrogen bond formation: an electron topology and orbital analysis. Birch, HL; Bozec, L; de Leeuw, NH; Nash, A; Saßmannshausen, J, 2017)
"Glucosepane is a novel AGE marker of diabetic complications that is robustly associated with nephropathic, retinopathic and neuropathic outcomes despite adjustment for A1c, suggesting that it could be one mediator of these complications with possible diagnostic implications."	( The association between skin collagen glucosepane and past progression of microvascular and neuropathic complications in type 1 diabetes. Cleary, PA; Genuth, S; Lachin, JM; Monnier, VM; Sell, DR; Strauch, C; Sun, W, )

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (23)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	1 (4.35)	29.6817
2010's	19 (82.61)	24.3611
2020's	3 (13.04)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	3 (12.50%)	5.53%
Reviews	3 (12.50%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	18 (75.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
imidazole imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.	2.52	2	0	imidazole
pyruvaldehyde Pyruvaldehyde: An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.. methylglyoxal : A 2-oxo aldehyde derived from propanal.	6.14	3	2	2-oxo aldehyde; propanals	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	7.05	9	2	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	2.21	1	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
ornithine Ornithine: An amino acid produced in the urea cycle by the splitting off of urea from arginine.. ornithine : An alpha-amino acid that is pentanoic acid bearing two amino substituents at positions 2 and 5.	2.17	1	0	non-proteinogenic L-alpha-amino acid; ornithine	algal metabolite; hepatoprotective agent; mouse metabolite
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	11.83	7	2	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
thiazoles [no description available]	2.1	1	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
methylguanidine Methylguanidine: A product of putrefaction. Poisonous.. methylguanidine : A guanidine in which one of the amino hydrogens of guanidine itself is substituted by a methyl group.	2.07	1	0	guanidines	EC 1.14.13.39 (nitric oxide synthase) inhibitor; metabolite; uremic toxin
deoxyglucose Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.	2.13	1	0
3-deoxyglucosone 3-deoxyglucosone: RN given refers to (D)-isomer. 3-deoxyglucosone : A deoxyketohexose comprising the open-chain form of D-glucose lacking the -OH group at the 3-position and having the keto group at the 2-position.	2.13	1	0	deoxyglucose; deoxyketohexose
pentosidine pentosidine: structure given in first source. pentosidine : An imidazopyridine having norleucine and ornithine residues attached via their side-chains at the 4- and 2-positions respectively.	6.36	4	2	imidazopyridine; non-proteinogenic L-alpha-amino acid	biomarker; cross-linking reagent
n(6)-carboxymethyllysine N(6)-carboxymethyllysine: RN given refers to (L)-isomer; structure given in first source. N(6)-carboxymethyl-L-lysine : An L-lysine derivative with a carboxymethyl substituent at the N(6)-position.	2.52	2	0	L-lysine derivative; non-proteinogenic L-alpha-amino acid	antigen
alagebrium alagebrium: an advanced glycation endproducts (AGE) cross-link breaker	2.1	1	0
3-nitrotyrosine 3-nitrotyrosine: RN given refers to parent cpd without isomeric designation. 3-nitrotyrosine : A nitrotyrosine comprising tyrosine having a nitro group at the 3-position on the phenyl ring.	2.21	1	0	2-nitrophenols; C-nitro compound; nitrotyrosine; non-proteinogenic alpha-amino acid
arginyllysine Arg-Lys : A dipeptide formed from L-arginyl and L-leucine residues.	2.17	1	0	dipeptide	metabolite
imidazolone imidazolone: a reaction product of arginine with 3-deoxyglucosone which markedly accumulates in uremic serum; structure in first source	7.11	1	0	organonitrogen heterocyclic compound
furosine [no description available]	5.85	2	2	alpha-amino acid

Condition	Relationship Strength	Studies	Trials
Diseases, Metabolic [description not available]	2.21	1	0
Metabolic Diseases Generic term for diseases caused by an abnormal metabolic process. It can be congenital due to inherited enzyme abnormality (METABOLISM, INBORN ERRORS) or acquired due to disease of an endocrine organ or failure of a metabolically important organ such as the liver. (Stedman, 26th ed)	2.21	1	0
Vascular Diseases Pathological processes involving any of the BLOOD VESSELS in the cardiac or peripheral circulation. They include diseases of ARTERIES; VEINS; and rest of the vasculature system in the body.	3.46	2	0
Diabetes Mellitus, Adult-Onset [description not available]	3.77	3	0
Albuminuria The presence of albumin in the urine, an indicator of KIDNEY DISEASES.	7.25	1	0
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	3.77	3	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	5.8	7	0
Cataract, Membranous [description not available]	2.31	1	0
Cataract Partial or complete opacity on or in the lens or capsule of one or both eyes, impairing vision or causing blindness. The many kinds of cataract are classified by their morphology (size, shape, location) or etiology (cause and time of occurrence). (Dorland, 27th ed)	2.31	1	0
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	2.31	1	0
Diabetic Retinopathy Disease of the RETINA as a complication of DIABETES MELLITUS. It is characterized by the progressive microvascular complications, such as ANEURYSM, interretinal EDEMA, and intraocular PATHOLOGIC NEOVASCULARIZATION.	2.58	2	0
Disease Exacerbation [description not available]	7.88	6	4
Osteoarthritis of Knee [description not available]	2.17	1	0
Osteoarthritis, Knee Noninflammatory degenerative disease of the knee joint consisting of three large categories: conditions that block normal synchronous movement, conditions that produce abnormal pathways of motion, and conditions that cause stress concentration resulting in changes to articular cartilage. (Crenshaw, Campbell's Operative Orthopaedics, 8th ed, p2019)	2.17	1	0
Complications of Diabetes Mellitus [description not available]	3.01	1	0
Autoimmune Diabetes [description not available]	8.08	6	5
Diabetic Angiopathies VASCULAR DISEASES that are associated with DIABETES MELLITUS.	3.9	2	1
Diabetic Glomerulosclerosis [description not available]	2.11	1	0
Diabetes Mellitus, Type 1 A subtype of DIABETES MELLITUS that is characterized by INSULIN deficiency. It is manifested by the sudden onset of severe HYPERGLYCEMIA, rapid progression to DIABETIC KETOACIDOSIS, and DEATH unless treated with insulin. The disease may occur at any age, but is most common in childhood or adolescence.	8.08	6	5
Diabetic Nephropathies KIDNEY injuries associated with diabetes mellitus and affecting KIDNEY GLOMERULUS; ARTERIOLES; KIDNEY TUBULES; and the interstitium. Clinical signs include persistent PROTEINURIA, from microalbuminuria progressing to ALBUMINURIA of greater than 300 mg/24 h, leading to reduced GLOMERULAR FILTRATION RATE and END-STAGE RENAL DISEASE.	2.11	1	0
Age-Related Osteoporosis [description not available]	3.94	1	0
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	3.94	1	0
Asymptomatic Conditions [description not available]	7.54	4	4
Vascular Calcification Deposition of calcium into the blood vessel structures. Excessive calcification of the vessels are associated with ATHEROSCLEROTIC PLAQUES formation particularly after MYOCARDIAL INFARCTION (see MONCKEBERG MEDIAL CALCIFIC SCLEROSIS) and chronic kidney diseases which in turn increase VASCULAR STIFFNESS.	7.54	4	4
Arterial Diseases, Carotid [description not available]	7.54	4	4
Arteriosclerosis, Coronary [description not available]	7.54	4	4
Cardiac Diseases [description not available]	7.54	4	4
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	7.54	4	4
Carotid Artery Diseases Pathological conditions involving the CAROTID ARTERIES, including the common, internal, and external carotid arteries. ATHEROSCLEROSIS and TRAUMA are relatively frequent causes of carotid artery pathology.	7.54	4	4
Coronary Artery Disease Pathological processes of CORONARY ARTERIES that may derive from a congenital abnormality, atherosclerotic, or non-atherosclerotic cause.	7.54	4	4
Heart Diseases Pathological conditions involving the HEART including its structural and functional abnormalities.	7.54	4	4
Disease A definite pathologic process with a characteristic set of signs and symptoms. It may affect the whole body or any of its parts, and its etiology, pathology, and prognosis may be known or unknown.	2.96	1	0

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