Physicochemical Properties
| Molecular Weight | 455.42404 |
| Exact Mass | 455.155 |
| Elemental Analysis | C, 52.75; H, 4.65; N, 21.53; O, 21.08 |
| CAS # | 2410-93-7 |
| PubChem CID | 135434845 |
| Appearance | Typically exists as solid at room temperature |
| Density | 1.61g/cm3 |
| Index of Refraction | 1.732 |
| LogP | 1.363 |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 10 |
| Rotatable Bond Count | 9 |
| Heavy Atom Count | 33 |
| Complexity | 798 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | OC(CC[C@H](NC(C1C=CC(N(CC2=CN=C3NC(=NC(=O)C3=N2)N)C)=CC=1)=O)C(=O)O)=O |
| InChi Key | HLIXOCXUWGDBNP-ZDUSSCGKSA-N |
| InChi Code | InChI=1S/C20H21N7O6/c1-27(9-11-8-22-16-15(23-11)18(31)26-20(21)25-16)12-4-2-10(3-5-12)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,8,13H,6-7,9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H3,21,22,25,26,31)/t13-/m0/s1 |
| Chemical Name | (2S)-2-[[4-[(2-amino-4-oxo-3H-pteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid |
| Synonyms | Methopterin; Methopterine; 2410-93-7; N10-Methylfolic acid; 10-Methylfolic acid; 10-Methylpteroylglutamic acid; N10-Methylpteroylglutamic acid; CHEMBL158990; |
| 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) |
Biological Activity
| Targets | MTX/methotrexate analog; DHFR/dihydrofolate reductase; osteoclasts proliferation |
| ln Vitro | This study is to observe the effects of methopterin on the activation and bone resorption function of murine osteoclasts, which were obtained by induction from bone marrow cell and purified to the purity of 70%-80%. The mechanism underlying the inhibitory effects of methopterin on inflammatory bone destruction was explored. MTT method was used to determine the effect of methopterin on the proliferation of osteoclasts. Flow cytometric analysis was used to determine the effect of methopterin on the apoptosis of osteocalsts. TRAP stain, bone resorption lacuna stain and measurement of lacuna area were executed to determine the effects of methopterin on the activation and function of osteoclasts. ELISA method was used to determine the effect of methopterin on the MMP-9 secretion from osteoclasts. RT-PCR method was used to determine the effect of methopterin on the mRNA expression of RANK and MMP-9 in osteoclasts. The results showed that methopterin (0.1-10 micromol x L(-1)) inhibited the proliferation of osteoclasts, methopterin (0.1-10 micromol x L(-1)) could inhibit the activation and bone resorption function of osteoclasts and induced the apoptosis of osteoclasts. Methopterin (0.01-10 micromol x L(-1)) also decreased the mRNA expression of RANK, but only at 1-10 micromol x L(-1) decreased the mRNA expression of MMP-9. These results indicated that there were intense relation between the inhibitory effects on the activation and function of osteoclasts and the inhibition of inflammatory bone destruction by methopterin [1]. |
| Toxicity/Toxicokinetics | mouse LDLo parenteral 1200 mg/kg Summary Tables of Biological Tests, National Research Council Chemical-Biological Coordination Center., 7(688), 1955 |
| References | [1]. Effects of methopterin on osteoclasts and study of its mechanism of action]. Yao Xue Xue Bao. 2008 Oct;43(10):1025-31. |
| Additional Infomation |
Methopterine is a member of folic acids. Methopterin is thought to have effects on osteoclasts and to inhibit inflammatory bone destruction. Mechanism of Action Methopterin has been shown to inhibit the proliferation, activation, and bone resorption action of osteoclasts, and induce the apoptosis of osteoclasts, likely contributing to the ability of methopterin to inhibit inflammatory bone destruction. |
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 : 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). 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 : PEG300：Tween 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). 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 | 2.1958 mL | 10.9789 mL | 21.9578 mL | |
| 5 mM | 0.4392 mL | 2.1958 mL | 4.3916 mL | |
| 10 mM | 0.2196 mL | 1.0979 mL | 2.1958 mL |