L-Methionine-(S,R)-Sulfoximine | CAS# 15985-39-4 | Glutamine Synthetase Inhibitor

MedKoo Cat#: 574004 | Name: L-Methionine-(S,R)-Sulfoximine

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Description:

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

L-Methionine-(S,R)-Sulfoximine is an inhibitor of glutamine synthetase and a sulfoximine derivative of L-methionine. It inhibits pea glutamine synthetase by 31 to 64% when used at concentrations ranging from 5 to 25 µM following preincubation with L-glutamine, an effect that is absent without L-glutamine preincubation. It also inhibits glutamine synthetase in isolated chick embryo retinas.

Chemical Structure

L-Methionine-(S,R)-Sulfoximine

CAS#15985-39-4

Theoretical Analysis

MedKoo Cat#: 574004

Name: L-Methionine-(S,R)-Sulfoximine

CAS#: 15985-39-4

Chemical Formula: C5H12N2O3S

Exact Mass: 180.0569

Molecular Weight: 180.22

Elemental Analysis: C, 33.32; H, 6.71; N, 15.54; O, 26.63; S, 17.79

Price and Availability

Size	Price	Availability
100mg	USD 250.00	2 Weeks
250mg	USD 400.00	2 Weeks
1g	USD 850.00	2 Weeks

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Synonym

L-Methionine-(S,R)-Sulfoximine; L-Methionine sulfoximine

IUPAC/Chemical Name

2S-amino-4-(S-methylsulfonimidoyl)-butanoic acid

InChi Key

SXTAYKAGBXMACB-DPVSGNNYSA-N

InChi Code

InChI=1S/C5H12N2O3S/c1-11(7,10)3-2-4(6)5(8)9/h4,7H,2-3,6H2,1H3,(H,8,9)/t4-,11?/m0/s1

SMILES Code

N[C@H](C(O)=O)CCS(C)(=N)=O

Appearance

Solid powder

Purity

>95% (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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

L-Methionine-DL-sulfoximine (MSX) is an inhibitor of glutamine synthetase.

In vitro activity:

Selective disruption of astrocyte oxidative metabolism has previously been shown to increase the propagation rate of SD (spreading depression) in vivo, but it is currently unknown whether astrocyte glycogen stores make significant contributions to the onset or propagation of SD. Consistent with these observations, exposure to l-methionine-dl-sulfoximine (MSO) increased slice glycogen levels and decreased OGD-SD propagation rates. Reference: Neuroscience. 2011 Sep 29;192:295-303. https://pubmed.ncbi.nlm.nih.gov/21600270/

In vivo activity:

A 5 min treatment with 3 mM MSO (L-methionine-DL-sulfoximine) increased the rate of efflux of newly loaded radiolabelled glutamine (Gln) from rat cortical astrocytes in primary culture to more than 400% of the basal efflux. Reference: Eur J Pharmacol. 1990 Jul 17;182(3):587-9. https://pubmed.ncbi.nlm.nih.gov/2171953/

	Solvent	mg/mL	mM
Solubility
	PBS (pH 7.2)	5.0	27.74
	Water	50.0	277.44

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 180.22 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. Seidel JL, Shuttleworth CW. Contribution of astrocyte glycogen stores to progression of spreading depression and related events in hippocampal slices. Neuroscience. 2011 Sep 29;192:295-303. doi: 10.1016/j.neuroscience.2011.05.006. Epub 2011 May 12. PMID: 21600270; PMCID: PMC3233357. 2. Zinovieva M, Fresneau C, Arrio B. Nitrogen source-dependent expression of a 126 kDa protein in the plasma membrane of the cyanobacterium Synechococcus PCC 7942. FEBS Lett. 1997 Oct 20;416(2):179-82. doi: 10.1016/s0014-5793(97)01199-x. PMID: 9369209. 3. Albrecht J, Norenberg MD. L-methionine-DL-sulfoximine induces massive efflux of glutamine from cortical astrocytes in primary culture. Eur J Pharmacol. 1990 Jul 17;182(3):587-9. doi: 10.1016/0014-2999(90)90061-a. PMID: 2171953.

In vitro protocol:

In vivo protocol:

1. Albrecht J, Norenberg MD. L-methionine-DL-sulfoximine induces massive efflux of glutamine from cortical astrocytes in primary culture. Eur J Pharmacol. 1990 Jul 17;182(3):587-9. doi: 10.1016/0014-2999(90)90061-a. PMID: 2171953.

1. Sinden, S.L., and Durbin, R.D. Glutamine synthetase inhibition: Possible mode of action of wildfire toxin from Pseudomonas tabaci. Nature 219(5152), 379-380 (1968). 2. Reif-Lehrer, L., and Coghlin, J. Conversion of glutamic acid to glutamine by retinal glutamine synthetase. Exp. Eye. Res. 17(4), 321-328 (1973).