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Merck

M5379

L-metionina sulfoximina

suitable for cell culture

Sinónimos:

L-S-(3-amino-3-carboxipropil)-S-metilsulfoximina

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Fórmula lineal:
CH3S(O)(=NH)CH2CH2CH(NH2)CO2H
Número CAS:
15985-39-4
Peso molecular:
180.23
UNSPSC Code:
12352116
NACRES:
NA.32
PubChem Substance ID:
24278555
MDL number:
MFCD00002621
Beilstein/REAXYS Number:
6175446

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Nombre del producto

L-metionina sulfoximina, suitable for cell culture

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 string

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

InChI key

SXTAYKAGBXMACB-DPVSGNNYSA-N

technique(s)

cell based assay: suitable
cell culture | mammalian: suitable

mp

>210 °C (dec.) (lit.)

suitability

suitable for molecular biology

Quality Level

300

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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.

Preparation Note

This product is stored at room temperature.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
0000503211
0000503211
0000498282
0000498281
0000498280

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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.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    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.

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
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)
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)
Davina Chai et al.
Journal of biotechnology, 131(4), 466-472 (2007-09-11)
A key challenge in molecular breeding of orchids is the creation of efficient and reproducible gene transformation systems. In this study, we report a new transformation method utilizing L-methionine sulfoximine (MSO) as a novel agent for selection of transgenic Dendrobium
Nuša Pristovšek et al.
Biotechnology journal, 13(3), e1700216-e1700216 (2018-01-24)
The selection of clonally derived Chinese hamster ovary (CHO) cell lines with the highest production rate of recombinant glycoproteins remains a big challenge during early stages of cell line development. Different strategies using either product titer or product titer normalized
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