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Wikipedia

Methylarginine

N-Methylarginine is an inhibitor of nitric oxide synthase.[1][2] Chemically, it is a methyl derivative of the amino acid arginine. It is used as a biochemical tool in the study of physiological role of nitric oxide.

Methylarginine

(S)-Methylarginine
Names
Other names
2-Amino-5-[(N’-methylcarbamimidoyl)amino]pentanoic acid; N-Monomethylarginine; omega-N-Methylarginine; Tilarginine; Targinine
Identifiers
  • 17035-90-4 (S) Y
3D model (JSmol)
  • Interactive image
2262067 (R)
ChEBI
  • CHEBI:28229 N
ChEMBL
  • ChEMBL312870 N
  • ChEMBL109350 N
  • ChEMBL256147 N
ChemSpider
  • 4213 N
  • 2015298 (R) N
  • 117259 (S) N
KEGG
  • C03884 N
MeSH omega-N-Methylarginine
  • 4366
  • 2733510 (R)
  • 132862 (S)
UNII
  • 27JT06E6GR Y
  • InChI=1S/C7H16N4O2/c1-10-7(9)11-4-2-3-5(8)6(12)13/h5H,2-4,8H2,1H3,(H,12,13)(H3,9,10,11) N
    Key: NTNWOCRCBQPEKQ-UHFFFAOYSA-N N
  • CNC(=N)NCCCC(N)C(O)=O
Properties
C7H16N4O2
Molar mass 188.231 g·mol−1
log P −0.63
Acidity (pKa) 2.512
Basicity (pKb) 11.488
Related compounds
Related alkanoic acids
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

The inhibiting effect of N-methylarginine on vasodilation is lower in hypertensive patients than in normal subjects, indicating endothelial dysfunction.[3] The inhibiting effect of N-methylarginine on vasodilation declines progressively with age, but has been restored with vitamin C in the oldest subjects.[3]

See also edit

References edit

  1. ^ Toutouzas, K.; Riga, M.; Stefanadi, E.; Stefanadis, C. (2008). "Asymmetric dimethylarginine (ADMA) and other endogenous nitric oxide synthase (NOS) inhibitors as an important cause of vascular insulin resistance". Hormone and Metabolic Research. 40 (9): 655–659. doi:10.1055/s-0028-1083814. PMID 18792879. S2CID 260167230.
  2. ^ Stefanovic-Racic M, Meyers K, Meschter C, Coffey JW, Hoffman RA, Evans CH (1994). "N-monomethyl arginine, an inhibitor of nitric oxide synthase, suppresses the development of adjuvant arthritis in rats". Arthritis & Rheumatology. 37 (7): 1062–1069. doi:10.1002/art.1780370712. PMID 7517676.
  3. ^ a b Taddei S, Virdis A, Ghiadoni L, Salvetti G, Bernini G, Magagna A, Salvetti A (2012). "Age-related reduction of NO availability and oxidative stress in human". Hypertension. 38 (2): 274–279. CiteSeerX 10.1.1.576.255. doi:10.1161/01.hyp.38.2.274. PMID 11509489. Up to the age of 60 years, despite the evident decline in endothelium-dependent vasodilation, vitamin C did not modify the response to acetylcholine. In contrast, in the oldest individuals (age >60 years) characterized by a profound alteration in NO availability, vitamin C not only enhanced the response to the endothelial agonist but also restored the inhibiting effect of L-NMMA on vasodilation to acetylcholine.

methylarginine, inhibitor, nitric, oxide, synthase, chemically, methyl, derivative, amino, acid, arginine, used, biochemical, tool, study, physiological, role, nitric, oxide, namesother, names, amino, methylcarbamimidoyl, amino, pentanoic, acid, monomethylargi. N Methylarginine is an inhibitor of nitric oxide synthase 1 2 Chemically it is a methyl derivative of the amino acid arginine It is used as a biochemical tool in the study of physiological role of nitric oxide Methylarginine S MethylarginineNamesOther names 2 Amino 5 N methylcarbamimidoyl amino pentanoic acid N Monomethylarginine omega N Methylarginine Tilarginine TarginineIdentifiersCAS Number 17035 90 4 S Y3D model JSmol Interactive imageBeilstein Reference 2262067 R ChEBI CHEBI 28229 NChEMBL ChEMBL312870 NChEMBL109350 NChEMBL256147 NChemSpider 4213 N2015298 R N117259 S NKEGG C03884 NMeSH omega N MethylargininePubChem CID 43662733510 R 132862 S UNII 27JT06E6GR YInChI InChI 1S C7H16N4O2 c1 10 7 9 11 4 2 3 5 8 6 12 13 h5H 2 4 8H2 1H3 H 12 13 H3 9 10 11 NKey NTNWOCRCBQPEKQ UHFFFAOYSA N NSMILES CNC N NCCCC N C O OPropertiesChemical formula C 7H 16N 4O 2Molar mass 188 231 g mol 1log P 0 63Acidity pKa 2 512Basicity pKb 11 488Related compoundsRelated alkanoic acids Asymmetric dimethylarginineN Propyl L arginineRelated compounds BuforminAcecarbromalExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references The inhibiting effect of N methylarginine on vasodilation is lower in hypertensive patients than in normal subjects indicating endothelial dysfunction 3 The inhibiting effect of N methylarginine on vasodilation declines progressively with age but has been restored with vitamin C in the oldest subjects 3 See also editAsymmetric dimethylarginineReferences edit Toutouzas K Riga M Stefanadi E Stefanadis C 2008 Asymmetric dimethylarginine ADMA and other endogenous nitric oxide synthase NOS inhibitors as an important cause of vascular insulin resistance Hormone and Metabolic Research 40 9 655 659 doi 10 1055 s 0028 1083814 PMID 18792879 S2CID 260167230 Stefanovic Racic M Meyers K Meschter C Coffey JW Hoffman RA Evans CH 1994 N monomethyl arginine an inhibitor of nitric oxide synthase suppresses the development of adjuvant arthritis in rats Arthritis amp Rheumatology 37 7 1062 1069 doi 10 1002 art 1780370712 PMID 7517676 a b Taddei S Virdis A Ghiadoni L Salvetti G Bernini G Magagna A Salvetti A 2012 Age related reduction of NO availability and oxidative stress in human Hypertension 38 2 274 279 CiteSeerX 10 1 1 576 255 doi 10 1161 01 hyp 38 2 274 PMID 11509489 Up to the age of 60 years despite the evident decline in endothelium dependent vasodilation vitamin C did not modify the response to acetylcholine In contrast in the oldest individuals age gt 60 years characterized by a profound alteration in NO availability vitamin C not only enhanced the response to the endothelial agonist but also restored the inhibiting effect of L NMMA on vasodilation to acetylcholine Retrieved from https en wikipedia org w index php title Methylarginine amp oldid 1213875953, wikipedia, wiki, book, books, library,

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