S-Methyl glutathione | CAS#2922-56-7 | peptide and glyoxylase inhibitor

MedKoo Cat#: 597081 | Name: S-Methylglutathione

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Description:

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

S-methylglutathione is a methionine containing peptide and glyoxylase inhibitor. S-methylglutathione is an S-substitued glutathione and a stronger nucleophile than GSH.

Chemical Structure

S-Methylglutathione

CAS#2922-56-7

Theoretical Analysis

MedKoo Cat#: 597081

Name: S-Methylglutathione

CAS#: 2922-56-7

Chemical Formula: C11H19N3O6S

Exact Mass: 321.0995

Molecular Weight: 321.34

Elemental Analysis: C, 41.11; H, 5.96; N, 13.08; O, 29.87; S, 9.98

Price and Availability

Size	Price	Availability
5mg	USD 350.00	2 Weeks
10mg	USD 500.00	2 Weeks
25mg	USD 700.00	2 Weeks

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Synonym

S-Methyl glutathione; Glutathione ester; Glutathione S-methyl ester;

IUPAC/Chemical Name

N5-((R)-1-((carboxymethyl)amino)-3-(methylthio)-1-oxopropan-2-yl)-L-glutamine

InChi Key

QTQDDTSVRVWHMO-BQBZGAKWSA-N

InChi Code

InChI=1S/C11H19N3O6S/c1-21-5-7(10(18)13-4-9(16)17)14-8(15)3-2-6(12)11(19)20/h6-7H,2-5,12H2,1H3,(H,13,18)(H,14,15)(H,16,17)(H,19,20)/t6-,7-/m0/s1

SMILES Code

O=C(O)CNC([C@H](CSC)NC(CC[C@@H](C(O)=O)N)=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 water

Shelf Life

>2 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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

S-methylglutathione has inhibitory effect on glyoxalase 1.

In vitro activity:

To be determined

In vivo activity:

Glutathione and its derivative S-methylglutathione have sedative and hypnotic effects, and might be effective in improving psychic stress, such as anxiety. After intracerebroventricular injection in neonatal chicks, this study found that S-methylglutathione did not form a disulfide bond due to the methylation of the SH group of the cysteine moiety. S-methylglutathione had similar effects as observed in reduced and oxidized glutathione. Reference: Neurosci Lett. 2007 May 11;418(1):87-91. https://pubmed.ncbi.nlm.nih.gov/17368722/

	Solvent	mg/mL	mM
Solubility
	Water	25.0	77.80

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 321.34 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.

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

Formulation protocol:

1. Yamane H, Tomonaga S, Suenaga R, Denbow DM, Furuse M. Intracerebroventricular injection of glutathione and its derivative induces sedative and hypnotic effects under an acute stress in neonatal chicks. Neurosci Lett. 2007 May 11;418(1):87-91. doi: 10.1016/j.neulet.2007.03.003. Epub 2007 Mar 3. PMID: 17368722. 2. Rius M, Nies AT, Hummel-Eisenbeiss J, Jedlitschky G, Keppler D. Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane. Hepatology. 2003 Aug;38(2):374-84. doi: 10.1053/jhep.2003.50331. PMID: 12883481.

In vitro protocol:

To be determined

In vivo protocol:

1: Toyoda A, Sato M, Muto M, Goto T, Miyaguchi Y, Inoue E. Metabolomic analyses of plasma and liver of mice fed with immature Citrus tumida peel. Biosci Biotechnol Biochem. 2020 Jun;84(6):1098-1104. doi: 10.1080/09168451.2020.1719821. Epub 2020 Feb 4. PMID: 32019425. 2: Park J, Kim J. Characterization of a B₁₂trafficking chaperone protein from caenorhabditis elegans. Protein Pept Lett. 2015;22(1):31-8. doi: 10.2174/0929866521666140919100346. PMID: 25256267. 3: Avlani VA, Ma W, Mun HC, Leach K, Delbridge L, Christopoulos A, Conigrave AD. Calcium-sensing receptor-dependent activation of CREB phosphorylation in HEK293 cells and human parathyroid cells. Am J Physiol Endocrinol Metab. 2013 May 15;304(10):E1097-104. doi: 10.1152/ajpendo.00054.2013. Epub 2013 Mar 26. PMID: 23531616. 4: Filipiak P, Hug GL, Bobrowski K, Pedzinski T, Kozubek H, Marciniak B. Sensitized photooxidation of s-methylglutathione in aqueous solution: intramolecular (S∴O) and (S∴N) bonded species. J Phys Chem B. 2013 Feb 28;117(8):2359-68. doi: 10.1021/jp312184e. Epub 2013 Feb 12. PMID: 23347005. 5: Kubienová L, Kopečný D, Tylichová M, Briozzo P, Skopalová J, Šebela M, Navrátil M, Tâche R, Luhová L, Barroso JB, Petřivalský M. Structural and functional characterization of a plant S-nitrosoglutathione reductase from Solanum lycopersicum. Biochimie. 2013 Apr;95(4):889-902. doi: 10.1016/j.biochi.2012.12.009. Epub 2012 Dec 27. PMID: 23274177. 6: Broadhead GK, Mun HC, Avlani VA, Jourdon O, Church WB, Christopoulos A, Delbridge L, Conigrave AD. Allosteric modulation of the calcium-sensing receptor by gamma-glutamyl peptides: inhibition of PTH secretion, suppression of intracellular cAMP levels, and a common mechanism of action with L-amino acids. J Biol Chem. 2011 Mar 18;286(11):8786-97. doi: 10.1074/jbc.M110.149724. Epub 2010 Dec 27. PMID: 21187282; PMCID: PMC3059007. 7: Staab CA, Hellgren M, Grafström RC, Höög JO. Medium-chain fatty acids and glutathione derivatives as inhibitors of S-nitrosoglutathione reduction mediated by alcohol dehydrogenase 3. Chem Biol Interact. 2009 Jun 15;180(1):113-8. doi: 10.1016/j.cbi.2009.01.008. Epub 2009 Jan 29. PMID: 19428350. 8: Mizuno N, Takahashi T, Kusuhara H, Schuetz JD, Niwa T, Sugiyama Y. Evaluation of the role of breast cancer resistance protein (BCRP/ABCG2) and multidrug resistance-associated protein 4 (MRP4/ABCC4) in the urinary excretion of sulfate and glucuronide metabolites of edaravone (MCI-186; 3-methyl-1-phenyl-2-pyrazolin-5-one). Drug Metab Dispos. 2007 Nov;35(11):2045-52. doi: 10.1124/dmd.107.016352. Epub 2007 Aug 6. PMID: 17682070. 9: Bobrowski K, Hug GL, Pogocki D, Marciniak B, Schöneich C. Sulfur radical cation-peptide bond complex in the one-electron oxidation of S-methylglutathione. J Am Chem Soc. 2007 Jul 25;129(29):9236-45. doi: 10.1021/ja072301f. Epub 2007 Jun 29. PMID: 17602483. 10: Yamane H, Tomonaga S, Suenaga R, Denbow DM, Furuse M. Intracerebroventricular injection of glutathione and its derivative induces sedative and hypnotic effects under an acute stress in neonatal chicks. Neurosci Lett. 2007 May 11;418(1):87-91. doi: 10.1016/j.neulet.2007.03.003. Epub 2007 Mar 3. PMID: 17368722. 11: Hasegawa M, Kusuhara H, Adachi M, Schuetz JD, Takeuchi K, Sugiyama Y. Multidrug resistance-associated protein 4 is involved in the urinary excretion of hydrochlorothiazide and furosemide. J Am Soc Nephrol. 2007 Jan;18(1):37-45. doi: 10.1681/ASN.2005090966. Epub 2006 Nov 29. PMID: 17135398. 12: Gerk PM, Li W, Megaraj V, Vore M. Human multidrug resistance protein 2 transports the therapeutic bile salt tauroursodeoxycholate. J Pharmacol Exp Ther. 2007 Feb;320(2):893-9. doi: 10.1124/jpet.106.106922. Epub 2006 Nov 15. PMID: 17108237. 13: Chin TY, Chueh SH, Tao PL. S-Nitrosoglutathione and glutathione act as NMDA receptor agonists in cultured hippocampal neurons. Acta Pharmacol Sin. 2006 Jul;27(7):853-60. doi: 10.1111/j.1745-7254.2006.00379.x. PMID: 16787569. 14: Romanyuk ND, Rigden DJ, Vatamaniuk OK, Lang A, Cahoon RE, Jez JM, Rea PA. Mutagenic definition of a papain-like catalytic triad, sufficiency of the N-terminal domain for single-site core catalytic enzyme acylation, and C-terminal domain for augmentative metal activation of a eukaryotic phytochelatin synthase. Plant Physiol. 2006 Jul;141(3):858-69. doi: 10.1104/pp.106.082131. Epub 2006 May 19. PMID: 16714405; PMCID: PMC1489916. 15: Ralat LA, Manevich Y, Fisher AB, Colman RF. Direct evidence for the formation of a complex between 1-cysteine peroxiredoxin and glutathione S-transferase pi with activity changes in both enzymes. Biochemistry. 2006 Jan 17;45(2):360-72. doi: 10.1021/bi0520737. PMID: 16401067.