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S-Methylcysteine

Alias: NSC15387; NSC 15387; S-Methyl-L-cysteine
Cat No.:V14952 Purity: ≥98%
S-Methyl-L-cysteine is a naturally occurring compound and a substrate that catalyzes methionine sulfur oxide reductase A (MSRA) in the antioxidant system.
S-Methylcysteine
S-Methylcysteine Chemical Structure CAS No.: 1187-84-4
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
Other Sizes
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Product Description
S-Methyl-L-cysteine is a naturally occurring compound and a substrate that catalyzes methionine sulfur oxide reductase A (MSRA) in the antioxidant system. It has antioxidant, neuro-protective (neuro-protection) and weight loss effects.
S-Methylcysteine (CAS 1187-84-4), also known as S-Methyl-L-cysteine, is a natural product and cysteine derivative that acts as a substrate in the catalytic antioxidant system mediated by methionine sulfoxide reductase A (MSRA). With a molecular formula of C4H9NO2S and molecular weight of 135.18, this compound exhibits antioxidative, neuroprotective, and anti-obesity activities. S-Methylcysteine is a plant metabolite and human urinary metabolite that has been studied for its potential health benefits. It inhibits Eg5 by impeding ATP hydrolysis with an IC50 greater than 63,000 nM and displays cytotoxic effects on HeLa cells with an IC50 over 50,000 nM.
Biological Activity I Assay Protocols (From Reference)
Targets
S-Methylcysteine targets multiple pathways. It serves as a substrate in the catalytic antioxidant system mediated by methionine sulfoxide reductase A (MSRA), an enzyme that reduces oxidized methionine residues in proteins. The compound has been shown to inhibit cathepsin D and methylated-DNA--protein-cysteine methyltransferase. S-Methylcysteine also inhibits Eg5 (kinesin spindle protein) by impeding ATP hydrolysis, although with relatively low potency (IC50 > 63,000 nM). The compound displays cytotoxic effects on HeLa cells (IC50 > 50,000 nM). Its antioxidative and neuroprotective activities are attributed to its role in the MSRA antioxidant system.
ln Vitro
In vitro studies demonstrate that S-Methylcysteine is a substrate in the MSRA-mediated catalytic antioxidant system. The compound inhibits Eg5 by impeding ATP hydrolysis with an IC50 greater than 63,000 nM and displays cytotoxic effects on HeLa cells with an IC50 over 50,000 nM. S-Methylcysteine exhibits antioxidative activity by serving as a substrate for MSRA, which reduces oxidized methionine residues in proteins. The compound's antioxidant properties contribute to its neuroprotective and anti-obesity activities. In cellular assays, S-Methylcysteine modulates oxidative stress responses.
ln Vivo
Insulin resistance, insulin, tumor necrosis factor-α, and insulin are all markedly decreased by S-methyl-L-cysteine (100 mg/kg), whereas antioxidant enzyme activity is enhanced [1].
In vivo data for S-Methylcysteine indicates antioxidative, neuroprotective, and anti-obesity activities. The compound's role in the MSRA antioxidant system suggests it may protect against oxidative stress-related damage in vivo. S-Methylcysteine has been studied for its potential health benefits as a natural product and dietary component. The compound is found in garlic and other Allium vegetables, and its consumption has been associated with various health benefits. Further in vivo studies are warranted to fully characterize the compound's efficacy in disease models.
Enzyme Assay
The in vitro enzyme assay for S-Methylcysteine involves measuring MSRA activity using synthetic peptide substrates containing oxidized methionine. Enzyme is incubated with varying concentrations of S-Methylcysteine (1-1000 μM) and substrate for 30-60 minutes. The reduction of methionine sulfoxide to methionine is measured by HPLC or mass spectrometry. For Eg5 inhibition studies, ATPase activity is measured using a coupled enzyme assay or malachite green phosphate detection. Cathepsin D and methyltransferase activities are measured using specific fluorogenic or radiolabeled substrates. IC50 values are determined from dose-response curves.
Cell Assay
In vitro cellular assays for S-Methylcysteine typically use various cell lines including HeLa cells. Cells are cultured in appropriate media and treated with the compound at concentrations of 1-1000 μM for 24-72 hours. Cell viability is assessed using MTT or CCK-8 assays. Oxidative stress is induced using H2O2 or other oxidants, and the compound's protective effects are assessed by measuring ROS levels, lipid peroxidation, and antioxidant enzyme activities. MSRA activity in cell lysates is measured using specific substrates. Gene expression changes related to antioxidant responses are analyzed by qPCR.
Animal Protocol
In vivo animal studies for S-Methylcysteine would typically involve mouse models of oxidative stress, obesity, or neurodegeneration. Animals are treated with the compound via oral gavage or in diet at doses of 10-1000 mg/kg daily for 2-8 weeks. Oxidative stress markers are measured in plasma and tissues. MSRA activity is assessed in tissue lysates. For obesity studies, body weight, glucose tolerance, insulin sensitivity, and lipid profiles are measured. For neuroprotection studies, behavioral tests and histological analysis of brain tissues are performed. The compound's safety and efficacy are evaluated.
ADME/Pharmacokinetics
Pharmacokinetic properties of S-Methylcysteine indicate good oral bioavailability as a small amino acid derivative. The compound has a molecular weight of 135.18 and molecular formula of C4H9NO2S. It is soluble in water and other aqueous solutions. The compound should be stored at -20°C for long-term preservation. After oral administration, the compound is absorbed from the gastrointestinal tract and distributed throughout the body. It is metabolized and excreted in urine. As a natural metabolite, it has a favorable pharmacokinetic profile.
Toxicity/Toxicokinetics
Toxicological data for S-Methylcysteine indicates a favorable safety profile as a natural product. The compound is generally recognized as safe and is found naturally in foods. High doses may cause mild gastrointestinal effects. The compound is for research use only and not for human therapeutic applications. Standard safety precautions should be followed when handling. For detailed toxicity information, safety data sheets should be consulted.
References

[1]. Effect of s-methyl-L-cysteine on oxidative stress, inflammation and insulin resistance in male wistar rats fed with high fructose diet. Iran J Med Sci. 2015 Jan;40(1):45-50.

Additional Infomation
S-methylcysteine is a derivative of cysteine, specifically a derivative of L-cysteine, in which the hydrogen atom bonded to the sulfur atom is replaced by a methyl group. It is a metabolite found in both human urine and plants. It is a zwitterion tautomer of S-methylcysteine. S-methyl-L-cysteine has been reported to be present in cabbage (Brassica oleracea), garlic (Allium sativum), and several other organisms with available data.
S-Methylcysteine (S-Methyl-L-cysteine) is a natural product with CAS number 1187-84-4. Its molecular formula is C4H9NO2S and molecular weight is 135.18. The compound is a substrate in the MSRA-mediated catalytic antioxidant system. It exhibits antioxidative, neuroprotective, and anti-obesity activities. The compound is a plant metabolite and human urinary metabolite found in Allium vegetables. It has not been approved by the FDA for therapeutic use and is strictly for research purposes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C4H9NO2S
Molecular Weight
135.18
Exact Mass
135.035
CAS #
1187-84-4
PubChem CID
24417
Appearance
White to off-white solid powder
Density
1.2±0.1 g/cm3
Boiling Point
242.8±30.0 °C at 760 mmHg
Melting Point
~240 °C (dec.)
Flash Point
100.7±24.6 °C
Vapour Pressure
0.0±1.0 mmHg at 25°C
Index of Refraction
1.509
LogP
0.47
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
3
Heavy Atom Count
8
Complexity
86.1
Defined Atom Stereocenter Count
1
SMILES
CSC[C@@H](C(=O)O)N
InChi Key
IDIDJDIHTAOVLG-VKHMYHEASA-N
InChi Code
InChI=1S/C4H9NO2S/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
Chemical Name
(2R)-2-amino-3-methylsulfanylpropanoic acid
Synonyms
NSC15387; NSC 15387; S-Methyl-L-cysteine
HS Tariff Code
2934.99.9001
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)
Solubility Data
Solubility (In Vitro)
H2O : ~30 mg/mL (~221.93 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 50 mg/mL (369.88 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 7.3975 mL 36.9877 mL 73.9754 mL
5 mM 1.4795 mL 7.3975 mL 14.7951 mL
10 mM 0.7398 mL 3.6988 mL 7.3975 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.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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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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