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M5379

L-Methionine sulfoximine

suitable for cell culture

Synonym(s):

L-S-(3-Amino-3-carboxypropyl)-S-methylsulfoximine

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About This Item

Linear Formula:
CH3S(O)(=NH)CH2CH2CH(NH2)CO2H
CAS Number:
Molecular Weight:
180.23
UNSPSC Code:
12352116
NACRES:
NA.32
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
6175446
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Quality Segment

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

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.[1]

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.[2]

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.[2]

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.

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This Item
10430991016T0254
technique(s)

cell based assay: suitable, cell culture | mammalian: suitable

technique(s)

-

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

technique(s)

-

Quality Level

300

Quality Level

500

Quality Level

300

Quality Level

200

suitability

suitable for molecular biology

suitability

suitable for manufacturing use

suitability

-

suitability

-

mp

>210 °C (dec.) (lit.)

mp

>210 °C (dec.) (lit.)

mp

>210 °C (dec.) (lit.)

mp

280-285 °C (dec.) (lit.)


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signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

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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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.

      Helpful?

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

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

      Helpful?

  3. 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.

      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.

      Helpful?

  6. 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).

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