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H-Met-Met-OH (L-Methionyl-L-methionine)

Cat No.:V61865 Purity: ≥98%
H-Met-Met-OH (L-Methionyl-L-methionine) is a dipeptide composed of two methionine residues.
H-Met-Met-OH (L-Methionyl-L-methionine)
H-Met-Met-OH (L-Methionyl-L-methionine) Chemical Structure CAS No.: 7349-78-2
Product category: Others 12
This product is for research use only, not for human use. We do not sell to patients.
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100mg
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Product Description
H-Met-Met-OH (L-Methionyl-L-methionine) is a dipeptide composed of two methionine residues.
H-Met-Met-OH (L-Methionyl-L-methionine) is a dipeptide composed of two L-methionine residues linked by a peptide bond. It is a synthetic dipeptide of considerable interest in biochemical research due to its relevance to sulfur-containing amino acid metabolism, peptide transport, and protein engineering. H-Met-Met-OH is also used as a dietary supplement and has been shown to have various health benefits in animals, including promoting α-s1 casein synthesis in bovine mammary gland explants.
Biological Activity I Assay Protocols (From Reference)
Targets
H-Met-Met-OH does not have a specific pharmacological target but is studied as a dipeptide involved in methionine metabolism and peptide transport. Methionine is an essential sulfur-containing amino acid involved in protein synthesis, methylation reactions, and antioxidant defense (via glutathione synthesis). The dipeptide form may have different transport properties and bioavailability compared to free methionine. H-Met-Met-OH may interact with peptide transporters (PEPT1, PEPT2) for intestinal absorption and cellular uptake, and may be hydrolyzed by intracellular peptidases to release free methionine.
ln Vitro
In vitro, H-Met-Met-OH has been studied for its effects on cell function and metabolism. It has been observed that methionyl-methionine promotes α-s1 casein synthesis in bovine mammary gland explants. The dipeptide may modulate protein synthesis and nitrogen metabolism. H-Met-Met-OH has been shown to have various health benefits in animals, including effects on growth, immune function, and antioxidant status. The compound's activity is concentration-dependent and may involve signaling pathways related to amino acid sensing (mTOR).
ln Vivo
In vivo, H-Met-Met-OH is orally active and has been studied as a dietary supplement in animals. It has been shown to have various health benefits including promoting growth, improving immune function, and enhancing antioxidant defense. The dipeptide form may provide advantages over free methionine in terms of bioavailability, stability, or targeted delivery. In livestock and poultry, methionine dipeptides are used as feed additives. However, specific in vivo data for H-Met-Met-OH are limited.
Enzyme Assay
Non-cell-based assays for H-Met-Met-OH involve characterization of its chemical properties, purity, and stability. Analytical methods including HPLC, LC-MS, and NMR are used to confirm identity and purity. The compound's solubility, stability in various buffers, and degradation products are characterized. In enzyme assays, the compound may be used as a substrate for peptidases to study dipeptide hydrolysis kinetics. Peptidase activity is measured by detecting free methionine or by monitoring substrate disappearance.
Cell Assay
Cellular assays for H-Met-Met-OH are performed using various cell lines, including mammary epithelial cells, intestinal cells, or immune cells. Cells are treated with H-Met-Met-OH at various concentrations, and cellular responses are measured. Protein synthesis is assessed by ³H-leucine or ³H-methionine incorporation. Cell proliferation is measured by MTT or CellTiter-Glo assays. Signaling pathways including mTOR and amino acid sensing are evaluated by Western blot. Methionine metabolism and glutathione levels are measured. The dipeptide's effects on cell function and metabolism are compared to free methionine.
Animal Protocol
In vivo experiments with H-Met-Met-OH are conducted in animal models including rodents, livestock, and poultry. Animals are administered H-Met-Met-OH via oral gavage, dietary supplementation, or injection. Growth performance, feed intake, body weight gain, and feed conversion ratio are measured. Immune function is assessed by antibody titers, cytokine production, and immune cell populations. Antioxidant status is evaluated by measuring glutathione levels, antioxidant enzyme activities, and oxidative stress markers. Methionine metabolism and protein synthesis are assessed in tissues.
ADME/Pharmacokinetics
H-Met-Met-OH is orally active and demonstrates favorable pharmacokinetic properties as a dipeptide. Following oral administration, the dipeptide is absorbed through peptide transporters (PEPT1) in the intestine and enters the bloodstream. It may be hydrolyzed by peptidases to release free methionine, which then enters methionine metabolism pathways. The compound's bioavailability, systemic exposure, and metabolic fate have been characterized in animal studies. The dipeptide form may provide advantages over free methionine in terms of stability and absorption kinetics.
Toxicity/Toxicokinetics
The toxicity profile of H-Met-Met-OH has been evaluated in the context of its use as a dietary supplement. Methionine is an essential amino acid, and at physiological doses, the dipeptide is considered safe and well-tolerated. At high doses, methionine can be toxic, and the same may apply to the dipeptide. Potential toxicities include hypermethioninemia, oxidative stress, and neurotoxicity at excessive doses. In animal studies, H-Met-Met-OH has been shown to be safe at dietary supplementation levels. Comprehensive toxicological studies are limited.
References
[1]. Lis MT, et, al. Effect of dietary changes on intestinal absorption of L-methionine and L-methionyl-L-methionine in the rat. Br J Nutr. 1972 Jan;27(1):159-67.
Additional Infomation
Met-Met is a dipeptide formed from two L-methionine residues. It is a metabolite of Mycoplasma genitalium. Functionally, it is related to L-methionine.
See also: Methionylmethionine (note moved to).
H-Met-Met-OH (CAS# 7349-78-2) is a dipeptide composed of two methionine residues with the molecular formula C₁₀H₂₀N₂O₃S₂ and a molecular weight of 280.41. It is also known as L-Methionyl-L-methionine and Met-Met. The compound is a dietary supplement that has been shown to have various health benefits in animals, including promoting α-s1 casein synthesis in bovine mammary gland explants. H-Met-Met-OH is orally active and is used in biochemical research on peptide transport, methionine metabolism, and protein engineering. As of current knowledge, H-Met-Met-OH is not approved as a therapeutic agent but is used as a research compound and dietary supplement.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H20N2O3S2
Molecular Weight
280.41
Exact Mass
280.092
CAS #
7349-78-2
PubChem CID
6993082
Appearance
Colorless to off-white solid powder
Density
1.237g/cm3
Boiling Point
555.1ºC at 760mmHg
Flash Point
289.5ºC
LogP
1.48
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
9
Heavy Atom Count
17
Complexity
252
Defined Atom Stereocenter Count
2
SMILES
CSCC[C@H](N)C(N[C@H](C(O)=O)CCSC)=O
InChi Key
ZYTPOUNUXRBYGW-YUMQZZPRSA-N
InChi Code
InChI=1S/C10H20N2O3S2/c1-16-5-3-7(11)9(13)12-8(10(14)15)4-6-17-2/h7-8H,3-6,11H2,1-2H3,(H,12,13)(H,14,15)/t7-,8-/m0/s1
Chemical Name
(2S)-2-[[(2S)-2-amino-4-methylsulfanylbutanoyl]amino]-4-methylsulfanylbutanoic acid
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

Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage.  (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
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)
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
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.5662 mL 17.8310 mL 35.6621 mL
5 mM 0.7132 mL 3.5662 mL 7.1324 mL
10 mM 0.3566 mL 1.7831 mL 3.5662 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.

Calculator

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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