Pentosidine

Chembox new
ImageFile=Pentosidine.pngImageSize=200px
IUPACName=(2"S")-2-Amino-6- [2- (4"S")- 4-amino-5-hydroxy-5- oxopentylamino-4-imidazo [4,5-b] pyridinyl] hexanoic acid
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Section1= Chembox Identifiers
CASNo=124505-87-9
PubChem=119593
SMILES=C1=CN(C2=NC(=NC2=C1)NCCCC (C(=O)O)N)CCCCC(C(=O)O)N
Section2= Chembox Properties
Formula=C₁₇H₂₆N₆O₄
MolarMass=378.42614
Appearance=
Density=
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Section3= Chembox Hazards
MainHazards=
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Autoignition=

Pentosidine is a biomarker for advanced glycation endproducts, or AGEs. It is a well characterized and easily detected member of this large class of compounds.

Background

AGEs are biochemicals formed continuously under normal circumstances, but more rapidly under a variety of stresses, especially oxidative stress and hyperglycemia. They serve as markers of stress and act as toxins themselves. Pentosidine is typical of the class, except that it fluoresces, which allows it to be seen and measured easily. Because it is well characterized, it is often studied to provide new insight into the biochemistry of AGE compounds in general.

Biochemistry

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.cite journal
journal=Kidney International |year=1998|volume= 53|pages= 416–422
doi=10.1046/j.1523-1755.1998.00756.x
url=http://www.nature.com/ki/journal/v53/n2/pdf/4490049a.pdf |format=pdf
title=Renal catabolism of advanced glycation end products: The fate of pentosidine
author=Toshio Miyata, Yasuhiko Ueda, Katsunori Horie, Masaomi Nangaku, Shuichi Tanaka, Charles van Ypersele de Strihou and Kiyoshi Kurokawa]

Although it is present only in trace concentrations among tissue proteins, it is useful for assessing cumulative damage to proteins—advanced glycation endproducts—by non-enzymatic browning reactions with carbohydrates.cite journal |author= DG Dyer, JA Blackledge, SR Thorpe and JW Baynes
title= Formation of pentosidine during nonenzymatic browning of proteins by glucose. Identification of glucose and other carbohydrates as possible precursors of pentosidine in vivo
journal= J. Biol. Chem.|url=http://www.jbc.org/cgi/content/abstract/266/18/11654
volume= 266|issue= 18|pages= 11654–11660|year= Jun, 1991 |pmid= |doi= |accessdate=2007-12-14] cite web |url=http://www.medscape.com/viewarticle/567316 |title=DHEA Restores Oxidative Balance in Type 2 Diabetes
author=Will Boggs
publisher=Medscape
accessdate=2007-12-14 |format= |work=] cite journal |author=Meerwaldt R, Graaff R, Oomen PH, "et al" |title=Simple non-invasive assessment of advanced glycation endproduct accumulation |journal=Diabetologia |volume=47 |issue=7 |pages=1324–30 |year=2004 |pmid=15243705 |doi=10.1007/s00125-004-1451-2 |accessdate=2007-12-15]

Physiology

"In vivo", AGEs form pentosidine through sugar fragmentation. In patients with Diabetes mellitus type 2, pentosidine correlates with the presence and severity of diabetic complications.cite journal
title=Pentosidine formation in skin correlates with severity of complications in individuals with long-standing IDDM.
author=Sell, D R : Lapolla, A : Odetti, P : Fogarty, J : Monnier, V M
journal=Diabetes|year= 1992 Oct|volume= 41|issue=10|pages= 1286–92
url=http://grande.nal.usda.gov/ibids/index.php?mode2=detail&origin=ibids_references&therow=166362
accessdate=2007-12-15
doi=10.2337/diabetes.41.10.1286]

References