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M5379

Sigma-Aldrich

L-Methionine sulfoximine

suitable for cell culture

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Synonym(s):
L-S-(3-Amino-3-carboxypropyl)-S-methylsulfoximine
Linear Formula:
CH3S(O)(=NH)CH2CH2CH(NH2)CO2H
CAS Number:
15985-39-4
Molecular Weight:
180.23
Beilstein:
6175446
MDL number:
MFCD00002621
UNSPSC Code:
12352116
PubChem Substance ID:
24278555
NACRES:
NA.32

Quality Level

300

technique(s)

cell based assay: suitable
cell culture | mammalian: suitable

mp

>210 °C (dec.) (lit.)

suitability

suitable for molecular biology

SMILES string

CS(=N)(=O)CC[C@H](N)C(O)=O

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

InChI key

SXTAYKAGBXMACB-DPVSGNNYSA-N

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Application

L-Methionine sulfoximine has been used as a potent inhibitor of glutamine synthetase (GS) activityto study its effect on the lifespan and disease progression in the SOD1 G93A mouse model for amyotrophic lateral sclerosis.

Use of high levels of MSX can enhance productivity and production stability in multiple recombinant GS CHO cell lines and GS–CHOK1SV cell lines without compromising product quality. These findings have important implications for improving the efficiency and reliability of industrial cell culture processes used in the production of biologics.

MSX, a potent convulsant, has shown a specific and significant impact on glutamine dynamics in primary cortical astrocyte cultures. This makes it a valuable compound for studying and modulating glutamine-related processes in cell culture.

Biochem/physiol Actions

As a potent inhibitor of glutamine synthetase activity (GS), this reagent has widely been used as a selection agent for plasmid integration in Chinese hamster ovary (CHO) and other mammalian cell lines. The growing demand for high yield cell banks for production of recombinant proteins for therapeutics has resulted in two major systems for selection of stable and active clones, Methotrexate selection of dihydrofolate reductase (DHFR) overexpressing cells and MSX selection of glutamine synthetase overexpressing cells. Cells are grown in the absence of glutamine in the media and inhibition of the endogenous activity of glutamine synthetase results in cell death for cells lacking overexpression. The MSX-glutamine synthetase selection mechanism provides benefits over that of the Methotrexate-DHFR system in that it typically requires a single amplification step and results in significant reduction of time to produce high stability, highly amplified clones. L-Methionine sulfoximine (MSX) enhances NH3 production in seedling leaves wheat, barley, corn and sorghum plants by inhibiting GS activity. MSX increases ornithine decarboxylase activity and decreases the survival rate in a model of transient cerebral ischemia.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

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    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. What is the solubility of Product M5379, L-Methionine sulfoximine?

    We test the solubility at 50 mg/mL (0.277 M) in water; heat and/or sonication may be required.

  6. What is the solution stability of Product M5379, L-Methionine sulfoximine?

    We do not have any information available on solution stability. The following references may provide some helpful information:1. Proc. Roy. Soc., 138, 265 (1951).2. Weisbrod, R. E., and Meister, A., Studies on Glutamine Synthetase from Escherichia Coli. Formation of Pyrrolidone Carboxylate and Inhibition by Methionine Sulfoximine. J.Biol. Chem., 248(11), 3997-4002 (1973).3. Richman, P. G., et al., Inhibition of Gamma-glutamylcysteine Synthetase by L-methionine-S-sulfoximine. J. Biol. Chem., 248(19), 6684-6690 (1973).

  7. How is Product M5379, L-Methionine sulfoximine, used?

    This product has been reported as an inhibitor of glutamine synthetase by  Weisbrod, R. E., et al., J.Biol. Chem., 248(11), 3997-4002 (1973).  It has also been reported as an inhibitor of γ-glutamylcysteine synthetase by Richman, P. G., et al., J. Biol. Chem., 248(19), 6684-6690 (1973).

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

L-methionine-DL-sulfoximine induces massive efflux of glutamine from cortical astrocytes in primary culture
Albrecht J and Norenberg MD, et al.
European journal of psychotraumatology, 182(3), 587-589 (1990)
Takeshi Omasa et al.
Current pharmaceutical biotechnology, 11(3), 233-240 (2010-03-10)
Mammalian cell lines are important host cells for the industrial production of pharmaceutical proteins owing to their capacity for correct folding, assembly and post-translational modification. In particular, Chinese hamster ovary (CHO) cells are the most dependable host cells for the
Increased MSX level improves biological productivity and production stability in multiple recombinant GS CHO cell lines
Tian Jun, et al.
Engineering in Life Sciences (2020)
Pivotal role of glutamine synthetase in ammonia detoxification
Hakvoort TB
Hepatology, 65, 281-293 (2017)
Nitrate transport and not photoinhibition limits growth of the freshwater Cyanobacterium synechococcus species PCC 6301 at low temperature.
Sakamoto T and Bryant DA
Plant Physiology, 119, 785?794-785?794 (1999)
View All Related Papers

Protocols

LC/MS Analysis of L-Methionine Sulfoximine and Sulfone on Ascentis® Express OH5

LC/MS Analysis of L-Methionine Sulfoximine and Sulfone on Ascentis® Express OH5

LC/MS Analysis of L-Methionine Sulfoximine, Sulfone and Sulfoxide on Ascentis® Express HILIC

Separation of L-Methionine sulfone; L-Methionine sulfoximine; L-Methionine sulfoxide

Chromatograms

application for HPLCapplication for HPLC

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