Pentosidine

Pentosidine

Names
IUPAC name (2S)-2-Amino-6-[2-[[(4S)- 4-amino-5-hydroxy-5-oxopentyl]]-4-imidazo [4,5-b]pyridinyl]hexanoic acid
Identifiers
CAS Number	124505-87-9
ChEBI	CHEBI:59951
ChemSpider	106787
Jmol interactive 3D	Image
PubChem	119593
InChI InChI=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/s1 Key: AYEKKSTZQYEZPU-RYUDHWBXSA-N InChI=1/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/s1 Key: AYEKKSTZQYEZPU-RYUDHWBXBF
SMILES C1=CN(C2=NC(=NC2=C1)NCCC[C@@H](C(=O)O)N)CCCC[C@@H](C(=O)O)N
Properties
Chemical formula	C17H26N6O4
Molar mass	378.43 g·mol^−1
Density	1.47 g/cm^3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.^[1]

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.^[2][3][4]

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.^[5]

References

1. Toshio Miyata, Yasuhiko Ueda, Katsunori Horie, Masaomi Nangaku, Shuichi Tanaka, Charles van Ypersele de Strihou and Kiyoshi Kurokawa (1998). "Renal catabolism of advanced glycation end products: The fate of pentosidine" (pdf). Kidney International 53 (2): 416–422. doi:10.1046/j.1523-1755.1998.00756.x. PMID 9461101.
2. DG Dyer, JA Blackledge, SR Thorpe and JW Baynes (Jun 1991). "Formation of pentosidine during nonenzymatic browning of proteins by glucose. Identification of glucose and other carbohydrates as possible precursors of pentosidine in vivo". J. Biol. Chem. 266 (18): 11654–11660. PMID 1904867. Retrieved 2007-12-14.
3. Will Boggs. "DHEA Restores Oxidative Balance in Type 2 Diabetes". Medscape. Archived from the original on 2008-01-07. Retrieved 2007-12-14.
4. Meerwaldt R, Graaff R, Oomen PH, et al. (2004). "Simple non-invasive assessment of advanced glycation endproduct accumulation". Diabetologia 47 (7): 1324–30. doi:10.1007/s00125-004-1451-2. PMID 15243705.
5. Sell, D R : Lapolla, A : Odetti, P : Fogarty, J : Monnier, V M (Oct 1992). "Pentosidine formation in skin correlates with severity of complications in individuals with long-standing IDDM.". Diabetes 41 (10): 1286–92. doi:10.2337/diabetes.41.10.1286. PMID 1397702. Retrieved 2007-12-15.