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HomeProduct name listL-METHIONINE SULFOXIMINE

L-METHIONINE SULFOXIMINE

Synonym(s):L-S-(3-Amino-3-carboxypropyl)-S-methylsulfoximine

  • CAS NO.:15985-39-4
  • Empirical Formula: C5H12N2O3S
  • Molecular Weight: 180.23
  • MDL number: MFCD00002621
  • EINECS: 629-483-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 23:02:33
L-METHIONINE SULFOXIMINE Structural

What is L-METHIONINE SULFOXIMINE?

Chemical properties

White Crystalline Powder

The Uses of L-METHIONINE SULFOXIMINE

L-Methionine sulfoximine has been used as a potent inhibitor of glutamine synthetase (GS) activity.

The Uses of L-METHIONINE SULFOXIMINE

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

The Uses of L-METHIONINE SULFOXIMINE

glutamine synthetase inhibitor, ornithine decarboxylase enhancer, convulsant

What are the applications of Application

L-Methionine [R,S]-Sulfoximine is an inhibitor of g-glutamylcysteine synthetase and glutamine synthetase

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.

Properties of L-METHIONINE SULFOXIMINE

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.  20-25°C
solubility  Aqueous Base (Slightly), Formic Acid (Slightly), Water (Sparingly, Sonicated)
form  Crystalline Powder
color  White or almost white
optical activity [α]20/D +10.8 to +14.0°, c = 1 in H2O
BRN  6175446
Stability: Temperature Sensitive
CAS DataBase Reference 15985-39-4(CAS DataBase Reference)

Safety information for L-METHIONINE SULFOXIMINE

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for L-METHIONINE SULFOXIMINE

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