| Size | Price | Stock | Qty |
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| 10mg |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg |
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| Other sizes |
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Purity: ≥98%
| Targets |
Glutamine synthetase
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|---|---|
| ln Vitro |
L-Methionine-DL-sulfoximine (MSO) is a potent convulsant which metabolically and morphologically primarily affects astroglia, and the links between the gliotoxic and neurophysiological effects of MSO are not clear. A 5 min treatment with 3 mM MSO increased the rate of efflux of newly loaded radiolabelled glutamine (Gln) from rat cortical astrocytes in primary culture to more than 400% of the basal efflux. MSO did not affect the efflux of the neurotransmitter amino acids GABA or D-aspartate (a non-metabolizable analogue of L-glutamate), under the same experimental conditions. MSO-induced overflow with Gln, which according to a recent account strongly interacts with the N-methyl-D-aspartate (NMDA) receptor complex, may contribute to the convulsive action of the drug [1].
The effect of L-methionine-DL-sulfoximine, an inhibitor of glutamine synthetase, on the formation of nitrate reductase in the wild-type strain of Neurospora in the presence of ammonium ions and of glutamine was studied. Under conditions in which glutamine synthetase was inactivated, it was found that only glutamine could repress nitrate reductase. In a mutant of Neurospora, gln-1b, which requires glutamine for growth, only glutamine could repress nitrate reductase. These results suggest a direct role for glutamine as corepressor of nitrate reductase in Neurospora [2]. |
| ln Vivo |
The administration of a single convulsant dose or of multiple subconvulsant doses of L-methionine-dl-sulfoximine (MSO) to 18-day old rats results in a significant elevation of the specific activity of cerebral tRNA methyltransferases, as determined in an in vitro assay, using heterologous or species-homologous tRNAs as substrates. The increase was detectable as early as 90 rain after MSQ4and persisted throughout the entire 5-6 h preconvulsant period. The [C -methyl tRNA was purified, and hydrolyzed to its constituent bases and their iI liquid chropatography. istribution was quantitated by high perfermance A marked increase in the formation of F Cl-N -methyland [Cl-N -dimethyl guanine was noted in the MSO-treated anima s, demonstratiig a specific stimulation by MS0 in vivo of the cerebral N*-methyl and/or N2-dimethyl guanine-specific tRNA methyltransferases.[3]
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| Enzyme Assay |
Enzyme assays [2].
(i) Nitrate reductase. NADPHnitrate reductase (EC 1.6.6.2) was assayed as described previously. One unit of nitrate reductase activity is defined as the production of 1 nmol of nitrite per min at 30°C; specific activity is given in terms of units of activity per milligam of protein. (ii) Glutamine synthetase. Glutamine synthetase (EC 6.3.1.2) was measured by its transferase activity as described by Ferguson and Sims. Determination ofprotein. Protein concentrations were determined by using biuret reagent (11) and crystalline bovine serum albumin as standard. In some cases protein concentrations during elution of partially purified preparations from a column were followed by measuring the absorbance at 235 nm [2]. |
| Cell Assay |
The basic medium without nitrogen source has been described and contained sucrose (20 g/liter) and macro- and micro-elements. One of the following nitrogen sources was included in the medium: ammonium tartrate, 4 g/liter (ammonia medium); glutamine, 2 g/liter (glutamine medium); sodium glutamate, 2 g/liter (glutamate medium); or sodium nitrate, 20 mM (induction medium). The wildtype strain was grown on ammonia medium or glutamine medium as required. Strain gln-lb was grown on glutamine medium. The culture conditions were as described previously. When the induction of nitrate was being studied, mycelial pads were grown from a conidial inoculum for 39 h at 27°C in standing culture, washed, subsequently transferred to induction medium (three pads per 30 ml of medium) supplemented or not with the test compound of interest at the required concentration, and then incubated with shaking for the desired time at 27°C. The mycelia were collected, washed with distilled water, blotted dry between paper towels, and either extracted immediately or stored frozen in liquid nitrogen. When the effect of MSX on the decay of nitrate reductase was studied, the mycelia were grown for 39 h in stationary culture at 27°C, subsequently transferred, and incubated in induction medium with shaking for 3.5 h to permit induction of nitrate reductase. The pads were then washed and transferred to induction medium supplemented with MSX (1 mM) plus 6 mM sodium tungstate (decay medium) and shaken for 3.5 h at 270C to permit decay of the active nitrate reductase in the absence of the synthesis of active enzyme. The mycelial pads were then harvested, washed with distilled water, blotted dry between paper towels, and extracted immediately or frozen and stored in liquid nitrogen [2].
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| Animal Protocol |
Sprague-Dawley'albino rats (la-days old) were injected intraperitoneally with either saline or MS0 (0.94 m moles/Kg for a single injection or 0.23 m moles/Kg every day for one week). The animals were decapitated 90 min, 3 h or 5 h after the single injection or on the eighth day after beginning the chronic 7-day treatment. The brain cortices were rapidly excised, weighed and homogenized in a glassteflon homogenizer in 3.5 vol of 10 mM Tris-HCl, pH 7.6, containing 1 mM dithiothreitol (DTT) and 1 mM MgCl . The homogenate was centrifuged at 165,000 x g for 150 min and the tR& methyltransferases precipitated from the clear supernatant by addition of a saturated solution of ammonium sulfate pH 7.0 to 80% (w/v) saturation. The insoluble material was recovered by centrifugation and the pellet resuspended in 10 mM Tris-HCl, pH 8.0 containing 1 mM EDTA and 1 mM DTT. This suspension was dialysed overnight against 1.5 1 of the same buffer (one buffer change) and the dialysate fraction used as a source of tRNA methyltransferases. [3]
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| References |
[3]. https://deepblue.lib.umich.edu/bitstream/handle/2027.42/22895/0000459.pdf;sequence=1
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| Additional Infomation |
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.
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| Molecular Formula |
C5H12N2O3S
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|---|---|
| Molecular Weight |
180.23
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| Exact Mass |
180.056
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| Elemental Analysis |
C, 33.32; H, 6.71; N, 15.54; O, 26.63; S, 17.79
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| CAS # |
15985-39-4
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| PubChem CID |
89034
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| Appearance |
White to off-white solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
352.2±52.0 °C at 760 mmHg
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| Melting Point |
>210ºC (dec.)(lit.)
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| Flash Point |
166.8±30.7 °C
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| Vapour Pressure |
0.0±1.7 mmHg at 25°C
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| Index of Refraction |
1.560
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| LogP |
-1.38
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
11
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| Complexity |
244
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CS(=N)(=O)CC[C@@H](C(=O)O)N
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| InChi Key |
SXTAYKAGBXMACB-DPVSGNNYSA-N
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| InChi Code |
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
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| Chemical Name |
2S-amino-4-(S-methylsulfonimidoyl)-butanoic acid
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| Synonyms |
L-Methionine-(S,R)-Sulfoximine; MSO; L-Methionine sulfoximine; MSX
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O: ~50 mg/mL (~277.4 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 100 mg/mL (554.85 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.5485 mL | 27.7423 mL | 55.4847 mL | |
| 5 mM | 1.1097 mL | 5.5485 mL | 11.0969 mL | |
| 10 mM | 0.5548 mL | 2.7742 mL | 5.5485 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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