MedKoo Cat#: 597356 | Name: S-Nitrosohomocysteine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

S-Nitrosohomocysteine is a DDAH Inhibitor.

Chemical Structure

S-Nitrosohomocysteine
S-Nitrosohomocysteine
CAS#139427-42-2

Theoretical Analysis

MedKoo Cat#: 597356

Name: S-Nitrosohomocysteine

CAS#: 139427-42-2

Chemical Formula: C4H8N2O3S

Exact Mass: 164.0256

Molecular Weight: 164.17

Elemental Analysis: C, 29.26; H, 4.91; N, 17.06; O, 29.23; S, 19.53

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
S-Nitrosohomocysteine;
IUPAC/Chemical Name
S-nitroso-L-homocysteine
InChi Key
QWPCKAAAWDCDCW-VKHMYHEASA-N
InChi Code
InChI=1S/C4H8N2O3S/c5-3(4(7)8)1-2-10-6-9/h3H,1-2,5H2,(H,7,8)/t3-/m0/s1
SMILES Code
N[C@@H](CCSN=O)C(O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 164.17 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Karver CE, Ahmed VF, Barrios AM. Oxidative inactivation of the lymphoid tyrosine phosphatase mediated by both general and active site directed NO donors. Bioorg Med Chem Lett. 2011 Jan 1;21(1):285-7. doi: 10.1016/j.bmcl.2010.11.025. Epub 2010 Nov 9. PubMed PMID: 21129966. 2: Morakinyo MK, Strongin RM, Simoyi RH. Modulation of homocysteine toxicity by S-nitrosothiol formation: a mechanistic approach. J Phys Chem B. 2010 Aug 5;114(30):9894-904. doi: 10.1021/jp103679v. PubMed PMID: 20666529. 3: Hong L, Fast W. Inhibition of human dimethylarginine dimethylaminohydrolase-1 by S-nitroso-L-homocysteine and hydrogen peroxide. Analysis, quantification, and implications for hyperhomocysteinemia. J Biol Chem. 2007 Nov 30;282(48):34684-92. Epub 2007 Sep 24. PubMed PMID: 17895252. 4: Chobanyan K, Thum T, Suchy MT, Zhu B, Mitschke A, Gutzki FM, Beckmann B, Stichtenoth DO, Tsikas D. GC-MS assay for hepatic DDAH activity in diabetic and non-diabetic rats by measuring dimethylamine (DMA) formed from asymmetric dimethylarginine (ADMA): evaluation of the importance of S-nitrosothiols as inhibitors of DDAH activity in vitro and in vivo in humans. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Oct 15;858(1-2):32-41. Epub 2007 Aug 7. PubMed PMID: 17825631. 5: Braun O, Knipp M, Chesnov S, Vasák M. Specific reactions of S-nitrosothiols with cysteine hydrolases: A comparative study between dimethylargininase-1 and CTP synthetase. Protein Sci. 2007 Aug;16(8):1522-34. Epub 2007 Jun 28. PubMed PMID: 17600152; PubMed Central PMCID: PMC2203367. 6: Broniowska KA, Zhang Y, Hogg N. Requirement of transmembrane transport for S-nitrosocysteine-dependent modification of intracellular thiols. J Biol Chem. 2006 Nov 10;281(45):33835-41. Epub 2006 Aug 7. PubMed PMID: 16893892; PubMed Central PMCID: PMC1839924. 7: Frey D, Braun O, Briand C, Vasák M, Grütter MG. Structure of the mammalian NOS regulator dimethylarginine dimethylaminohydrolase: A basis for the design of specific inhibitors. Structure. 2006 May;14(5):901-11. PubMed PMID: 16698551. 8: Zhang Y, Hogg N. S-Nitrosothiols: cellular formation and transport. Free Radic Biol Med. 2005 Apr 1;38(7):831-8. Review. PubMed PMID: 15749378. 9: Knipp M, Braun O, Vasák M. Searching for DDAH inhibitors: S-nitroso-L-homocysteine is a chemical lead. J Am Chem Soc. 2005 Mar 2;127(8):2372-3. PubMed PMID: 15724974. 10: Lee SJ, Kim KM, Namkoong S, Kim CK, Kang YC, Lee H, Ha KS, Han JA, Chung HT, Kwon YG, Kim YM. Nitric oxide inhibition of homocysteine-induced human endothelial cell apoptosis by down-regulation of p53-dependent Noxa expression through the formation of S-nitrosohomocysteine. J Biol Chem. 2005 Feb 18;280(7):5781-8. Epub 2004 Nov 23. PubMed PMID: 15561702. 11: Jakubowski H. Molecular basis of homocysteine toxicity in humans. Cell Mol Life Sci. 2004 Feb;61(4):470-87. Review. PubMed PMID: 14999406. 12: Jakubowski H. Homocysteine-thiolactone and S-nitroso-homocysteine mediate incorporation of homocysteine into protein in humans. Clin Chem Lab Med. 2003 Nov;41(11):1462-6. Review. PubMed PMID: 14656026. 13: Root P, Mutus B. O-Aminobenzoyl-S-nitrosohomocysteine, a fluorogenic probe for cell-surface thiol determinations via a microtiter plate assay. Anal Biochem. 2003 Sep 15;320(2):299-302. PubMed PMID: 12927837. 14: Toubin C, Yeung DY, English AM, Peslherbe GH. Theoretical evidence that Cu(I) complexation promotes degradation of S-nitrosothiols. J Am Chem Soc. 2002 Dec 18;124(50):14816-7. PubMed PMID: 12475301. 15: Cassone Faldetta M, Laurenti O, Desideri G, Bravi MC, De Luca O, Marinucci MC, De Mattia G, Ferri C. L-arginine infusion decreases plasma total homocysteine concentrations through increased nitric oxide production and decreased oxidative status in Type II diabetic patients. Diabetologia. 2002 Aug;45(8):1120-7. Epub 2002 Jun 22. PubMed PMID: 12189442. 16: Akhter S, Vignini A, Wen Z, English A, Wang PG, Mutus B. Evidence for S-nitrosothiol-dependent changes in fibrinogen that do not involve transnitrosation or thiolation. Proc Natl Acad Sci U S A. 2002 Jul 9;99(14):9172-7. Epub 2002 Jun 27. PubMed PMID: 12089331; PubMed Central PMCID: PMC123113. 17: Fu WY, Dudman NP, Perry MA, Wang XL. Homocysteine attenuates hemodynamic responses to nitric oxide in vivo. Atherosclerosis. 2002 Mar;161(1):169-76. PubMed PMID: 11882329. 18: Jakubowski H. Protein N-homocysteinylation: implications for atherosclerosis. Biomed Pharmacother. 2001 Oct;55(8):443-7. Review. PubMed PMID: 11686577. 19: Al-Mustafa AH, Sies H, Stahl W. Sulfur-to-nitrogen transnitrosation: transfer of nitric oxide from S-nitroso compounds to diethanolamine and the role of intermediate sulfur-to-sulfur transnitrosation. Toxicology. 2001 Jun 21;163(2-3):127-36. PubMed PMID: 11516522. 20: Ramachandran N, Root P, Jiang XM, Hogg PJ, Mutus B. Mechanism of transfer of NO from extracellular S-nitrosothiols into the cytosol by cell-surface protein disulfide isomerase. Proc Natl Acad Sci U S A. 2001 Aug 14;98(17):9539-44. Epub 2001 Aug 7. PubMed PMID: 11493694; PubMed Central PMCID: PMC55488.