| Revision as of 08:52, 10 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wiki← Previous edit |
Latest revision as of 14:46, 30 October 2024 edit undoJakob Suckale (talk | contribs)Extended confirmed users1,403 editsm decoding scientific lingo: circaseptan for easier reading |
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{{chembox |
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{{Chembox |
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| verifiedrevid = 444022832 |
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| verifiedrevid = 444023988 |
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|ImageFile=Neopterin.svg |
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| ImageFile = Neopterin.svg |
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|ImageSize= |
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| ImageSize = |
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|IUPACName=2-amino-6-(1,2,3-trihydroxypropyl)-1''H''-pteridin-4-one |
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| PIN = 2-Amino-6-(1,2,3-trihydroxypropyl)pteridin-4(1''H'')-one |
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|OtherNames= |
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| OtherNames = |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 2009-64-5 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 448839 |
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| CASNo = 2009-64-5 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 9PLD60N7SO |
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| PubChem = 448839 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 395518 |
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| ChemSpiderID = 395518 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB02385 |
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| DrugBank = DB02385 |
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| SMILES = O=C2\N=C(/Nc1ncc(nc12)(O)(O)CO)N |
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| SMILES = O=C2\N=C(/Nc1ncc(nc12)(O)(O)CO)N |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI=1S/C9H11N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h1,4,6,15-17H,2H2,(H3,10,11,13,14,18)/t4-,6+/m1/s1 |
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| StdInChI = 1S/C9H11N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h1,4,6,15-17H,2H2,(H3,10,11,13,14,18)/t4-,6+/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey=BMQYVXCPAOLZOK-XINAWCOVSA-N |
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| StdInChIKey = BMQYVXCPAOLZOK-XINAWCOVSA-N |
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| SMILES2 = C1=C(N=C2C(=N1)NC(=NC2=O)N)C(C(CO)O)O |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB02385 |
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| MeSHName = Neopterin |
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}} |
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| SMILES=C1=C(N=C2C(=N1)NC (=NC2=O)N)C(C(CO)O)O |
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|Section2={{Chembox Properties |
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| MeSHName=Neopterin |
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| Formula = C<sub>9</sub>H<sub>11</sub>N<sub>5</sub>O<sub>4</sub> |
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}} |
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| MolarMass = 253.215 g/mol |
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|Section2= {{Chembox Properties |
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| Appearance = |
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| Formula=C<sub>9</sub>H<sub>11</sub>N<sub>5</sub>O<sub>4</sub> |
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| Density = 2.02 g/cm<sup>3</sup> |
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| MolarMass=253.215 g/mol |
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| MeltingPt = |
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|Section3={{Chembox Hazards |
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| Solubility= |
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}} |
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| FlashPt = |
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|Section3= {{Chembox Hazards |
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| AutoignitionPt = |
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'''Neopterin''' is a ] product of ] (GTP), a ] ]. |
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'''Neopterin''' is an ] belonging to the pteridine class of ]s. |
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Neopterin belongs to the chemical group known as ]s. It is synthesised by human ]s upon stimulation with the ] ] and is indicative of a pro-inflammatory immune status. Neopterin serves as a marker of ] activation.<ref> Cavaleri et al. Blood concentrations of neopterin and biopterin in subjects with depression: A systematic review and meta-analysis ''Progress in Neuro-Psychopharmacology and Biological Psychiatry'' 2023. 120:110633. http://dx.doi.org/10.1016/j.pnpbp.2022.110633 </ref> In humans neopterin follows a circadian (daily) and circaseptan (weekly) rhythm.<ref>Seizer L, Cornélissen-Guillaume G, Schiepek GK, Chamson E, Bliem HR and Schubert C (2022) About-Weekly Pattern in the Dynamic Complexity of a Healthy Subject’s Cellular Immune Activity: A Biopsychosocial Analysis. Front. Psychiatry 13:799214. doi: 10.3389/fpsyt.2022.799214</ref> |
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==Biosynthesis== |
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Neopterin belongs to the chemical group known as ]s. It is synthesised by ]s upon stimulation with the ] ] and is indicative of a pro-inflammatory immune status. Neopterin serves as a marker of ] activation. |
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The biosynthesis of neopterin occurs in two steps from ] (GTP). The first being catalyzed by ], which opens the ribose group. Phosphatases next catalyze the hydrolysis of the phosphate ester group.<ref>{{cite journal |doi=10.1016/s0889-1591(02)00006-5|title=Neopterin production, tryptophan degradation, and mental depression—What is the link? |year=2002 |last1=Widner |first1=Bernhard |last2=Laich |first2=Andreas |last3=Sperner-Unterweger |first3=Barbara |last4=Ledochowski |first4=Maximilian |last5=Fuchs |first5=Dietmar |journal=Brain, Behavior, and Immunity |volume=16 |issue=5 |pages=590–595 |pmid=12401473 |s2cid=35800171 }}</ref> |
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==Neopterin as disease marker== |
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==Neopterin as disease marker== |
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Measurement of neopterin concentrations in body fluids like ], ] or ] provides information about activation of cellular immune activation in humans under the control of ] type 1. High neopterin production is associated with increased production of ], neopterin concentrations also allow to estimate the extent of ] elicited by the ]. |
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Measurement of neopterin concentrations in body fluids like ], ] or ] provides information about activation of cellular immune activation in humans under the control of ] type 1. High neopterin production is associated with increased production of ], neopterin concentrations also allow to estimate the extent of ] elicited by the ]. <ref> Cavaleri et al. Blood concentrations of neopterin and biopterin in subjects with depression: A systematic review and meta-analysis ''Progress in Neuro-Psychopharmacology and Biological Psychiatry'' 2023. 120:110633. http://dx.doi.org/10.1016/j.pnpbp.2022.110633 </ref> |
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Increased neopterin production is found in, but not limited to, the following diseases: |
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Increased neopterin production is found in, but not limited to, the following diseases: |
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*]s including ] (HIV), ] and ] |
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*]s including ] (HIV), ] and ], ], ]. |
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*]s by intracellular living ] such as '']'' (]), '']'', and '']''. |
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*] such as '']'' (]) |
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*] such as ] (RA) and ] (SLE) |
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*] diseases |
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*] rejection episodes. |
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*A ] called ]<ref>{{Cite book | chapter-url=https://www.ncbi.nlm.nih.gov/bookshelf/br.fcgi?book=gene&part=ags |title = GeneReviews |chapter = Aicardi-Goutières Syndrome|publisher = University of Washington, Seattle|year = 1993|pmid = 20301648 |last1 = Adam |first1 = M. P. |last2 = Mirzaa |first2 = G. M. |last3 = Pagon |first3 = R. A. |last4 = Wallace |first4 = S. E. |author5 = Bean LJH |last6 = Gripp |first6 = K. W. |last7 = Amemiya |first7 = A. |last8 = Crow |first8 = Y. J. }}</ref> |
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*]<ref> Cavaleri et al. Blood concentrations of neopterin and biopterin in subjects with depression: A systematic review and meta-analysis ''Progress in Neuro-Psychopharmacology and Biological Psychiatry'' 2023. 120:110633. http://dx.doi.org/10.1016/j.pnpbp.2022.110633 </ref> and somatization. |
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Neopterin concentrations usually correlate with the extent and activity of the disease, and are also useful to monitor during therapy in these patients. Elevated neopterin concentrations are among the best predictors of adverse outcome in patients with HIV infection, in cardiovascular disease and in various types of cancer. |
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*]s by intracellular living ] such as ] (]) and ] |
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In the laboratory it is measured by ] (RIA), ], or high-performance liquid chromatography (HPLC).<ref> Cavaleri et al. Blood concentrations of neopterin and biopterin in subjects with depression: A systematic review and meta-analysis ''Progress in Neuro-Psychopharmacology and Biological Psychiatry'' 2023. 120:110633. http://dx.doi.org/10.1016/j.pnpbp.2022.110633 </ref> It has a native ] of wavelength excitation at 353 nm and emission at 438 nm, rendering it readily detected. |
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*] such as ] (]) |
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==References== |
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*] such as ] (RA) and ] (SLE) |
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* Cavaleri et al. Blood concentrations of neopterin and biopterin in subjects with depression: A systematic review and meta-analysis. Progr Neuropsychopharmacol Biol Psychiatry 2023;120:110633. |
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* Murr C, et al. Neopterin as a marker for immune system activation. Curr Drug Metabol 2002;3:175-187. |
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* Fuchs D, et al. The role of neopterin in atherogenesis and cardiovascular risk stratification. Curr Med Chem 2009;16:4644-4653. |
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* Sucher R, et al. Neopterin, a prognostic marker in human malignancies. Cancer Lett 2010;287:13-22. |
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* Zeng B, et al. Serum neopterin for early assessment of severity of severe acute respiratory syndrome. Clin Immunol 2005;116(1):18-26. |
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* Roberston J, et al. Serum neopterin levels in relation to mild and severe COVID-19. BMC Infect Dis 2020;20(1):942. |
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*] diseases |
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*] rejection episodes. |
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*A ] called ]<ref>http://www.ncbi.nlm.nih.gov/bookshelf/br.fcgi?book=gene&part=ags</ref> |
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Neopterin concentrations usually correlate with the extent and activity of the disease, and are also useful to monitor during therapy in these patients. Elevated neopterin concentrations are among the best predictors of adverse outcome in patients with HIV infection, in cardiovascular disease and in various types of cancer. |
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In the laboratory it is measured by ] (RIA), ], or high-performance liquid chromatography (HPLC). It has a native ] of wavelength excitation at 353 nm and emission at 438 nm, rendering it readily detected. |
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==References== |
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{{Reflist}} |
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==External links== |
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