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Merck

M5379

Sigma-Aldrich

L-metionina sulfoximina

suitable for cell culture

Sinónimos:

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

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About This Item

Fórmula lineal:
CH3S(O)(=NH)CH2CH2CH(NH2)CO2H
Número de CAS:
Peso molecular:
180.23
Beilstein:
6175446
Número MDL:
Código UNSPSC:
12352116
ID de la sustancia en PubChem:
NACRES:
NA.32
En este momento no podemos mostrarle ni los precios ni la disponibilidad

técnicas

cell based assay: suitable
cell culture | mammalian: suitable

mp

>210 °C (dec.) (lit.)

idoneidad

suitable for molecular biology

cadena SMILES

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

Clave InChI

SXTAYKAGBXMACB-DPVSGNNYSA-N

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Aplicación

L-Methionine sulfoximine has been used as a potent inhibitor of glutamine synthetase (GS) activity[1][2]to study its effect on the lifespan and disease progression in the SOD1 G93A mouse model for amyotrophic lateral sclerosis.[3]

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.[4][5]

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.[5]

Acciones bioquímicas o fisiológicas

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.[6] MSX increases ornithine decarboxylase activity and decreases the survival rate in a model of transient cerebral ischemia.

Almacenamiento y estabilidad

This product is stored at room temperature.

Pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

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

Órganos de actuación

Respiratory system

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves


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Certificados de análisis (COA)

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Visite la Librería de documentos

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)
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)
Effect of Methionine Sulfoximine on the Accumulation of Ammonia in C3 and C4 Leaves
Martin F
Plant Physiology, 71, 177-181 (1983)

Questions

1–6 of 6 Questions  
  1. Dear colleagues, i need to know about the stability of MSX (reference M5379) in water or medium. A stock solution of 10 mM could be stored at +4? iF YES, for howlong? Kind regards samia

    1 answer
    1. The stability of this specific product in solution has not been determined. However, a similar product, GSS-1015-F, a 100mM L-Methionine sulfoximine solution, is stored at -20 deg. C. and is assigned a shelf life of 1 year. See below for a link to this product page: https://www.sigmaaldrich.com/product/mm/gss1015.

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  2. What is the storage temperature of this product (M5379)?

    1 answer
    1. This product is stored at room temperature.

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

    1 answer
    1. 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).

      Helpful?

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

    1 answer
    1. 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).

      Helpful?

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

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

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

    1 answer
    1. 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.

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