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Merck
CN

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 Level

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.

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.


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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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Protocols

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

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


Pivotal role of glutamine synthetase in ammonia detoxification
Hakvoort TB
Hepatology, 65, 281-293 (2017)
Effect of Methionine Sulfoximine on the Accumulation of Ammonia in C3 and C4 Leaves
Martin F
Plant Physiology, 71, 177-181 (1983)
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)



Global Trade Item Number

SKUGTIN
M5379-1G04061834059844
M5379-250MG04061834059851
M5379-500MG04061834059868
M5379-5G04061835506439