| Identification | More | [Name]
L-METHIONINE SULFOXIMINE | [CAS]
15985-39-4 | [Synonyms]
2-AMINO-4-(S-METHYLSULFONIMIDOSYL)BUTANOIC ACID
L-METHIONINE-DL-SULFOXIMINE
L-METHIONINE SULFOXIMINE
L-S-[3-AMINO-3-CARBOXYPROPYL]-S-METHYLSULFOXIMINE
(2S)-2-Amino-4-(S-methylsulfonimidosyl)butanoic acid
L-Methionine [R,S]-Sulfoximine
L-S-[3-Amino-3-carboxypropyl]-S-methyl-[R,S]-sulfoximine
L-Methionine sulfoximine, 98+% | [EINECS(EC#)]
629-483-1 | [Molecular Formula]
C5H12N2O3S | [MDL Number]
MFCD00002621 | [Molecular Weight]
180.23 | [MOL File]
15985-39-4.mol |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Powder | [Melting point ]
>210 °C (dec.)(lit.) | [Boiling point ]
352.2±52.0 °C(Predicted) | [density ]
1.215 (estimate) | [refractive index ]
1.6430 (estimate) | [storage temp. ]
0-6°C | [solubility ]
Aqueous Base (Slightly), Formic Acid (Slightly), Water (Sparingly, Sonicated) | [form ]
Crystalline Powder | [color ]
White or almost white | [biological source]
synthetic | [optical activity]
[α]20/D +10.8 to +14.0°, c = 1 in H2O | [Usage]
Methionine sulfoximine inhibits both glutamine synthetase and g-glutamylcysteine synthetase. Working concentrations for inhibition of g-glutamylcysteine synthetase are 0.2-2.0 mM (52% inhibition occured at 100 mM).
Methionine sulfoximine is also | [BRN ]
6175446 | [Stability:]
Temperature Sensitive | [CAS DataBase Reference]
15985-39-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29309090 |
| Hazard Information | Back Directory | [Chemical Properties]
White Crystalline Powder | [Uses]
L-Methionine sulfoximine has been used as a potent inhibitor of glutamine synthetase (GS) activity. | [Uses]
glutamine synthetase inhibitor, ornithine decarboxylase enhancer, convulsant | [Uses]
Methionine sulfoximine inhibits both glutamine synthetase and g-glutamylcysteine synthetase. Working concentrations for inhibition of g-glutamylcysteine synthetase are 0.2-2.0 mM (52% inhibition occured at 100 mM).
Methionine sulfoximine is also a toxic | [Definition]
ChEBI: L-methionine sulfoximine is a methionine sulfoximine in which the amino group has S-stereochemistry. It has a role as a geroprotector and an EC 6.3.1.2 (glutamate--ammonia ligase) inhibitor. It is a methionine sulfoximine, a L-methionine derivative and a non-proteinogenic L-alpha-amino acid. It is a tautomer of a L-methionine sulfoximine zwitterion. | [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. | [in vivo]
L-Methionine-DL-sulfoximine (75 mg/kg, i.p., 210 min) exerts no affect on the hippocampal Gutamine synthetase (GS) activity and the expression of GS protein for the first 150 min, but significantly decreases the activity of GS during 165-210 min in rats. Additionally, L-Methionine-DL-sulfoximine also reduces the intensity of convulsive seizures (CS) caused by Pilocarpine (Pilo) (HY-B0726A) administration and seizure in rats[1].
L-Methionine-DL-sulfoximine (75 mg/kg, i.p.) reduces D-Asp release evoked by K+-induced depolarization and unchanges Glu uptake in the hippocampus and enthorhinal cortex of temporal lobe epilepsy (TLE) model rats[4].
| Animal Model: | Male rats (24 days old, Sprague Dawley)[1] | | Dosage: | 75 mg/kg | | Administration: | 210 min, i.p., measurements were taken at MSO “0”, after 15 min (referred to as MSO “15”, Pilo “15” and MSO + Pilo “15”) and after 60 min (MSO “60”, Pilo “60” and MSO + Pilo “60”, respectively | | Result: | Did not affect the hippocampal GS activity and the expression of GS protein for the first 150 min, but significantly decreased the activity during 165-210 min after MSO administration in rats. Additionally, MSO reduced the intensity of CS caused by Pilo administration. |
| Animal Model: | Hippocampus and enthorhinal cortex of TLE model rats[4] | | Dosage: | 75 mg/kg | | Administration: | i.p., Administration 150 minutes before decapitation | | Result: | Markedly reduced D-Asp release evoked by K+-induced depolarization and slightly decreased [3H]D-Asp uptake at higher concentrations of [3H]D-Asp in TLE model rats. |
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