pentosidine

Pentosidine
	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
PubChem	119593
Jmol-3D images	Image 1
	SMILES C1=CN(C2=NC(=NC2=C1)NCCCC (C(=O)O)N)CCCCC(C(=O)O)N ;
Properties
Molecular formula	C17H26N6O4
Molar mass	378.43 g mol−1
Density	1.47 g/cm3
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/04/10 03:36:45」(JST)

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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

^ 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.
^ 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. Check date values in: |date= (help)
^ Will Boggs. "DHEA Restores Oxidative Balance in Type 2 Diabetes". Medscape. Archived from the original on 2008-01-07. Retrieved 2007-12-14.
^ 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. |accessdate= requires |url= (help)
^ Sell, D R : Lapolla, A : Odetti, P : Fogarty, J : Monnier, V M (1992 Oct). "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. Check date values in: |date= (help)

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English Journal

Serum advanced glycation endproducts are associated with left ventricular dysfunction in normal glucose metabolism but not in type 2 diabetes: The Hoorn Study.

Linssen PB1, Henry RM1, Schalkwijk CG1, Dekker JM2, Nijpels G3, Brunner-La Rocca HP4, Stehouwer CD5.
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The pecking order of skin Advanced Glycation Endproducts (AGEs) as long-term markers of glycemic damage and risk factors for micro- and subclinical macrovascular disease progression in Type 1 diabetes.

Monnier VM1,2, Genuth S3, Sell DR4.
Glycoconjugate journal.Glycoconj J.2016 Jun 25. [Epub ahead of print]
To date more than 20 glycation products were identified, of which ~15 in the insoluble human skin collagen fraction. The goal of this review is to streamline 30 years of research and ask a set of important questions: in Type 1 diabetes which glycation products correlate best with 1) past mean glyce
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Association between Asymmetric Dimethylarginine and Pentosidine in Dialysis Effluent of Peritoneal Dialysis Patients -A possible intraperitoneal crosstalk between asymmetric dimethylarginine and advanced glycation end products in peritoneal dialysis patients.

Ishida M1, Kakuta T, Miyakogawa T, Tatsumi R, Matsumoto C, Fukagawa M.
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OBJECTIVE: Asymmetric dimethylarginine (ADMA) is an endogenous inhibitor of endothelial nitric oxide synthase. Elevated serum ADMA concentration is associated with impaired vascular endothelial function. We examined the relationships of ADMA with pentosidine, a representative advanced glycation end
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Related Pictures

Pentosidine Pentosidine is one of the Maillard ペントシジン（Pentosidine pentosidine in plasma to assay pentosidine Figure 6 - Pentosidine Levels by Age Pentosidine (CAS 124505-87-9) Structure of fluorophore P (Pentosidine

[Miyata-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.

[Dyer1-2] 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. Check date values in: |date= (help)

[Mescape_DHEA-3] Will Boggs. "DHEA Restores Oxidative Balance in Type 2 Diabetes". Medscape. Archived from the original on 2008-01-07. Retrieved 2007-12-14.

[Meerwaldt-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. |accessdate= requires |url= (help)

[Sell-5] Sell, D R : Lapolla, A : Odetti, P : Fogarty, J : Monnier, V M (1992 Oct). "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. Check date values in: |date= (help)

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