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| Other Sizes |
| Targets |
L-Methionine sulfoxide targets the cellular redox system and is involved in the regulation of oxidative stress. It is a substrate for methionine sulfoxide reductase enzymes (MSRA and MSRB), which catalyze its reduction back to methionine. This redox cycle plays an important role in protecting proteins from oxidative damage, as methionine residues can act as endogenous antioxidants. The compound also modulates purinergic signaling parameters and can induce M1/classical macrophage polarization. Through these mechanisms, L-methionine sulfoxide is involved in the regulation of inflammatory responses and cellular redox homeostasis.
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| ln Vitro |
Commercial ergot supplements have been made from amino acids and their derivatives. They affect the release of anabolic hormones, the availability of fuel for activity, the ability to think clearly under pressure, and the prevention of muscular damage brought on by exertion. They are regarded as advantageous synergistic food ingredients [1].
In vitro, L-methionine sulfoxide has been shown to affect various cellular processes. It can modulate oxidative stress parameters in cell culture models and influence purinergic signaling pathways. The compound induces M1/classical macrophage polarization, suggesting a role in inflammatory responses. It is also used as a substrate in enzyme assays to measure the activity of methionine sulfoxide reductase, where the reduction of the sulfoxide to methionine is monitored. These in vitro studies help to elucidate the role of methionine oxidation in cellular physiology and pathology, including its involvement in aging, neurodegenerative diseases, and inflammatory conditions. |
| ln Vivo |
In vivo, L-methionine sulfoxide is an endogenous metabolite that is formed under conditions of oxidative stress. It is present in various tissues and biological fluids and serves as a biomarker of oxidative damage. The compound can be reduced back to methionine by methionine sulfoxide reductase enzymes, which play a protective role against oxidative stress. Animal studies have shown that modulation of methionine sulfoxide levels can affect inflammatory responses and oxidative stress parameters. The compound may also be used in dietary studies to investigate the effects of oxidized amino acids on health and disease. However, L-methionine sulfoxide is not a therapeutic drug but rather a research tool for studying redox biology.
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| Enzyme Assay |
In vitro enzyme assays for L-methionine sulfoxide typically measure the activity of methionine sulfoxide reductase (MSR). A standard protocol involves incubating the substrate (L-methionine sulfoxide) with an enzyme preparation containing MSR, such as cell lysates or purified enzyme, in the presence of a reducing system (e.g., dithiothreitol or thioredoxin/thioredoxin reductase). The reaction is allowed to proceed at physiological pH and temperature, and the production of methionine is quantified by HPLC, mass spectrometry, or enzymatic methods. The decrease in methionine sulfoxide concentration or the increase in methionine concentration is measured to determine enzyme activity. These assays are used to study the regulation of MSR activity and to screen for compounds that modulate this enzyme.
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| Cell Assay |
In vitro cellular assays using L-methionine sulfoxide are conducted to study its effects on cellular redox status, inflammation, and signaling pathways. A typical protocol involves treating cultured cells, such as macrophages or neuronal cells, with varying concentrations of the compound. After incubation, cellular parameters such as reactive oxygen species (ROS) levels, cytokine production, and signaling pathway activation are measured. The compound's ability to induce M1 macrophage polarization can be assessed by measuring the expression of M1 markers such as iNOS and IL-6. These experiments help to elucidate the role of methionine oxidation in cellular physiology and its involvement in inflammatory and neurodegenerative diseases.
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| Animal Protocol |
In vivo animal studies with L-methionine sulfoxide are typically conducted to study oxidative stress, inflammation, and the role of methionine oxidation in disease. A typical protocol involves administering the compound to rodents via oral gavage, intraperitoneal injection, or dietary supplementation. Tissues and blood samples are collected to measure methionine sulfoxide levels, oxidative stress markers, and inflammatory parameters. The effects on macrophage polarization, cytokine production, and organ function can be assessed. These studies help to understand the role of methionine sulfoxide in conditions such as aging, neurodegenerative diseases, and metabolic disorders. The compound may also be used in dietary intervention studies to investigate the effects of oxidized amino acids on health.
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| ADME/Pharmacokinetics |
As an endogenous metabolite, L-methionine sulfoxide is present in plasma and tissues at varying concentrations. It is formed from methionine by reactive oxygen species and is reduced back to methionine by methionine sulfoxide reductase enzymes. The compound is distributed throughout the body and can cross the blood-brain barrier. Its levels are influenced by oxidative stress and the activity of reductase enzymes. In pharmacokinetic studies, the compound is typically measured in biological samples using HPLC or mass spectrometry. Its half-life and clearance are determined by the balance between formation and reduction. These properties are important for understanding its role as a biomarker of oxidative stress.
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| Toxicity/Toxicokinetics |
L-Methionine sulfoxide is generally considered to have low toxicity, as it is an endogenous metabolite present in the body. However, elevated levels of methionine sulfoxide are associated with oxidative stress and have been linked to various pathological conditions, including neurodegenerative diseases, aging, and inflammation. The compound is not classified as a toxic substance, but its accumulation may indicate oxidative damage. In research settings, standard laboratory safety precautions are recommended when handling the compound. It is not a drug and is not intended for therapeutic use.
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| References |
[1]. Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144.
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| Additional Infomation |
L-Methionine sulfoxide (H-Met(O)-OH, CAS 91183-71-0) is an oxidized form of the essential amino acid methionine. Its chemical formula is C₅H₁₁NO₃S and molecular weight is 165.21. It is an endogenous metabolite formed from methionine by oxidative damage and can be reduced back to methionine by methionine sulfoxide reductase. The compound can induce M1 macrophage polarization and modulates oxidative stress and purinergic signaling. It is used in research to study oxidative stress, protein oxidation, and inflammation. It is not a drug and is intended for research use only.
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| Molecular Formula |
C9H20CLNO2S
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| Molecular Weight |
241.7786
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| Exact Mass |
241.09
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| CAS # |
91183-71-0
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| PubChem CID |
13141795
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| Appearance |
White to off-white solid powder
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| Density |
1.033g/cm3
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| Boiling Point |
280.6ºC at 760 mmHg
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| Flash Point |
123.5ºC
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| Index of Refraction |
1.485
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| LogP |
2.91
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
14
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| Complexity |
166
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C(=O)(OC(C)(C)C)[C@@H](N)CCSC.Cl
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| InChi Key |
KZJQROCWHZGZBJ-FJXQXJEOSA-N
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| InChi Code |
InChI=1S/C9H19NO2S.ClH/c1-9(2,3)12-8(11)7(10)5-6-13-4;/h7H,5-6,10H2,1-4H3;1H/t7-;/m0./s1
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| Chemical Name |
tert-butyl (2S)-2-amino-4-methylsulfanylbutanoate;hydrochloride
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.1360 mL | 20.6800 mL | 41.3599 mL | |
| 5 mM | 0.8272 mL | 4.1360 mL | 8.2720 mL | |
| 10 mM | 0.4136 mL | 2.0680 mL | 4.1360 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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