 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C19H32N6O11S3 |
| Molecular Weight | 616.69 |
| Exact Mass | 598.119 |
| CAS # | 200393-05-1 |
| Related CAS # | S-Adenosyl-L-methionine tosylate;52248-03-0;S-Adenosyl-L-methionine-d3;68684-40-2;S-Adenosyl-L-methionine;29908-03-0;S-Adenosyl-L-methionine-13C;74084-24-5 |
| PubChem CID | 71587625 |
| Appearance | Typically exists as solid at room temperature |
| LogP | 1.979 |
| Hydrogen Bond Donor Count | 6 |
| Hydrogen Bond Acceptor Count | 16 |
| Rotatable Bond Count | 11 |
| Heavy Atom Count | 39 |
| Complexity | 794 |
| Defined Atom Stereocenter Count | 5 |
| SMILES | CSCCC(NCC1C(OS(CCCCS(O)(=O)=O)(=O)=O)C(O)C(N2C3=NC=NC(N)=C3N=C2)O1)C(O)=O |
| InChi Key | TYXBLACMHQBEEW-XKGORWRGSA-N |
| InChi Code | InChI=1S/C15H22N6O5S.C4H10O6S2/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21;5-11(6,7)3-1-2-4-12(8,9)10/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25);1-4H2,(H,5,6,7)(H,8,9,10)/t7-,8+,10+,11+,14+,27?;/m0./s1 |
| Chemical Name | (2S)-2-amino-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-methylsulfonio]butanoate;butane-1,4-disulfonic 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 |
| 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
| ln Vitro | In Cal-33 and JHU-SCC-011 cells, S-Adenosyl-L-methionine (300 µM, 24 or 48 h) 1,4-butanedisulfonate induces apoptosis and increases cell cycle arrest [4]. Adenosyl-L-methionine (300 µM, 24 h) 1,4-butanedisulfonate inhibits JHU-SCC-011 and Cal-33 cell migration [4]. By controlling the production of DNMTs, S-adenosyl-L-methionine (5–40 μg/mL, 48 h) 1,4-butanedisulfonate safeguards the anti-cancer activity of 5-FU [5]. |
| ln Vivo | S-adenosyl-L-methionine (30 mg/kg, taken orally over three days) Early postnatal rats exposed to valproic acid do not exhibit ASD-like behaviors when 1,4-butanedisulfonate is administered [6]. S-Adenosyl-L-methionine (oral, 50 and 100 mg/kg) In a rat model of epilepsy generated by pentylenetetrazole, 1,4-butanedisulfonate has anti-epileptic, memory-enhancing, and antioxidant effects [7]. |
| Cell Assay |
Apoptosis Analysis[4] Cell Types: Cal-33 and JHU-SCC- 011 cells Tested Concentrations: 300 µM Incubation Duration: 24 h (Cal-33) or 48 h (HU-SCC-011) Experimental Results: demonstrated an approximately 10% and 3% of apoptotic cells respectively. Cell Cycle Analysis[4] Cell Types: Cal-33 and JHU-SCC-011 cells Tested Concentrations: 300 µM Incubation Duration: 24 h (Cal-33) or 48 h (HU-SCC-011) Experimental Results: diminished the expression of cyclin B1, E1 and D1 in the Cal- 33 and JHU-SCC-011 cells. |
| Animal Protocol |
Animal/Disease Models: Valproic acid treated young mice[6] Doses: 30 mg/kg Route of Administration: po, for 3 days Experimental Results: Alleviated most ASD like neurobehavioral symptoms. Normalized the redox potential in the prefrontal cortex. |
| References |
[1]. G M Bressa. S-adenosyl-l-methionine (SAMe) as antidepressant: meta-analysis of clinical studies. Acta Neurol Scand Suppl. 1994;154:7-14. [2]. S-adenosyl methionine (SAMe) versus celecoxib for the treatment of osteoarthritis symptoms: a double-blind cross-over trial. [ISRCTN36233495]. BMC Musculoskelet Disord. 2004 Feb 26;5:6. [3]. S-adenosylmethionine in liver health, injury, and cancer. Physiol Rev. 2012 Oct;92(4):1515-42. [4]. Effects of S‑adenosyl‑L‑methionine on the invasion and migration of head and neck squamous cancer cells and analysis of the underlying mechanisms. Int J Oncol. 2020 May;56(5):1212-1224. [5]. S-adenosyl methionine specifically protects the anticancer effect of 5-FU via DNMTs expression in human A549 lung cancer cells. Mol Clin Oncol. 2013 Mar;1(2):373-378. [6]. S-adenosyl methionine prevents ASD like behaviors triggered by early postnatal valproic acid exposure in very young mice. Neurotoxicol Teratol. 2019 Jan-Feb;71:64-74. [7]. Evaluation of antiepileptic effect of S-adenosyl methionine and its role in memory impairment in pentylenetetrazole-induced kindling model in rats. Epilepsy Behav. 2016 Aug;61:153-157. |
| Additional Infomation | Physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in treatment of chronic liver disease. (From Merck, 11th ed) |
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 | 1.6216 mL | 8.1078 mL | 16.2156 mL | |
| 5 mM | 0.3243 mL | 1.6216 mL | 3.2431 mL | |
| 10 mM | 0.1622 mL | 0.8108 mL | 1.6216 mL |