1.02011-09-21 00:26:58 UTC2015-07-21 06:57:36 UTCFDB023252PentosidinePentosidine is a carbohydrate-derived advanced glycation end products (AGEs) that is considerably elevated in uremic patients. Derived from ribose, a pentose, pentosidine forms fluorescent cross-links between the arginine and lysine residues in collagen. It is formed in a reaction of the amino acids with the Maillard reaction products of ribose. Although it is present only in trace concentrations among tissue proteins, it is useful for assessing cumulative damage to proteins-advanced glycation endproductsThis compound per se has no biological activities but is highly correlated to the levels of precursors of carbonyl compounds, and for this reason is considered a reliable surrogate marker for AGEs. The modification of proteins in uremia is not limited to AGEs, since advanced lipoxidation end products are also demonstrable in plasma proteins in uremia. The accumulation of these compounds does not seem to be dependent only on the decline of renal function. Carbonyl precursors of AGEs and advanced lipoxidation end products are markedly elevated in uremic patients. Preliminary cross-sectional studies in haemodialysis patients seem to indicate that the AGEs and carbonyl stress may be involved in the pathogenesis of alterations in left ventricular geometry and function in these patients. (PMID 11051031)
The plasma pentosidine level in diabetic nephropathy was found to be determined by factors such as renal function control of glucose and the patient's age; of these, renal function was the most critical factor. The pathological role of AGEs in diabetic nephropathy, is in the expanded mesangial area of diffuse diabetic glomerulosclerosis, with nodular lesions, characteristic of diabetic nephropathy. These suggests a potential link of AGEs accumulation, which may be determined by renal function, control of glucose and age, to renal tissue damage in diabetic nephropathy. (PMID 9044316)
The rate of accumulation of glycoxidation products is accelerated in diabetes and age-adjusted concentrations of two advanced glycation end-products (AGE) in tissue proteins, N(6)-carboxymethyllysine and pentosidine, correlate with the severity of complication in diabetic patients. (PMID 9044306) [HMDB]pentosidineC17H26N6O4378.4261378.20155335(2S)-2-amino-6-(2-{[(4S)-4-amino-4-carboxybutyl]amino}-4H-imidazo[4,5-b]pyridin-4-yl)hexanoic acidpentosidine124505-87-9N[C@@H](CCCCN1C=CC=C2N=C(NCCC[C@H](N)C(O)=O)N=C12)C(O)=OInChI=1S/C17H26N6O4/c18-11(15(24)25)5-1-2-9-23-10-4-7-13-14(23)22-17(21-13)20-8-3-6-12(19)16(26)27/h4,7,10-12H,1-3,5-6,8-9,18-19H2,(H,20,21)(H,24,25)(H,26,27)/t11-,12-/m0/s1AYEKKSTZQYEZPU-RYUDHWBXSA-N belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.L-alpha-amino acidsOrganic compoundsOrganic acids and derivativesCarboxylic acids and derivativesAmino acids, peptides, and analoguesAromatic heteropolycyclic compoundsAmino acidsAmino fatty acidsAzacyclic compoundsCarbonyl compoundsCarboxylic acidsDicarboxylic acids and derivativesHeteroaromatic compoundsHeterocyclic fatty acidsHydrocarbon derivativesImidazolesImidazopyridinesMedium-chain fatty acidsMonoalkylaminesOrganic oxidesOrganopnictogen compoundsPyridines and derivativesAmineAmino acidAmino fatty acidAromatic heteropolycyclic compoundAzacycleAzoleCarbonyl groupCarboxylic acidDicarboxylic acid or derivativesFatty acidFatty acylHeteroaromatic compoundHeterocyclic fatty acidHydrocarbon derivativeImidazoleImidazopyridineL-alpha-amino acidMedium-chain fatty acidOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPrimary aliphatic aminePrimary aminePyridineimidazopyridinenon-proteinogenic L-alpha-amino acidSolidlogp-3.73logs-3.34solubility1.73e-01 g/llogp-3.9pka_strongest_acidic1.51pka_strongest_basic9.83iupac(2S)-2-amino-6-(2-{[(4S)-4-amino-4-carboxybutyl]amino}-4H-imidazo[4,5-b]pyridin-4-yl)hexanoic acidaverage_mass378.4261mono_mass378.20155335smilesN[C@@H](CCCCN1C=CC=C2N=C(NCCC[C@H](N)C(O)=O)N=C12)C(O)=OformulaC17H26N6O4inchiInChI=1S/C17H26N6O4/c18-11(15(24)25)5-1-2-9-23-10-4-7-13-14(23)22-17(21-13)20-8-3-6-12(19)16(26)27/h4,7,10-12H,1-3,5-6,8-9,18-19H2,(H,20,21)(H,24,25)(H,26,27)/t11-,12-/m0/s1inchikeyAYEKKSTZQYEZPU-RYUDHWBXSA-Npolar_surface_area169.38refractivity99.61polarizability40.55rotatable_bond_count12acceptor_count9donor_count5physiological_charge0formal_charge0Specdb::CMs15413Specdb::CMs38674Specdb::CMs136739Specdb::CMs144473Specdb::NmrOneD34962Specdb::NmrOneD34963Specdb::NmrOneD34964Specdb::NmrOneD34965Specdb::NmrOneD34966Specdb::NmrOneD34967Specdb::NmrOneD34968Specdb::NmrOneD34969Specdb::NmrOneD34970Specdb::NmrOneD34971Specdb::NmrOneD34972Specdb::NmrOneD34973Specdb::NmrOneD34974Specdb::NmrOneD34975Specdb::NmrOneD34976Specdb::NmrOneD34977Specdb::NmrOneD34978Specdb::NmrOneD34979Specdb::NmrOneD34980Specdb::NmrOneD34981Specdb::MsMs87852Specdb::MsMs87853Specdb::MsMs87854Specdb::MsMs150453Specdb::MsMs150454Specdb::MsMs150455Specdb::MsMs2769359Specdb::MsMs2769360Specdb::MsMs2769361Specdb::MsMs2912945Specdb::MsMs2912946Specdb::MsMs2912947HMDB03933#<Reference:0x0000555675d8fdf8>#<Reference:0x0000555675d8fc40>#<Reference:0x0000555675d8fa88>#<Reference:0x0000555675d8f8a8>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823