ChemicalBook Product Catalog Biochemical Engineering Amino Acids and Derivatives Methionine derivatives 5'-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5'-deoxyadenosine inner salt, 1,4-butanedisulfonate

5'-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5'-deoxyadenosine inner salt, 1,4-butanedisulfonate

Product Name5'-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5'-deoxyadenosine inner salt, 1,4-butanedisulfonate
CAS200393-05-1
MFC15H22N6O5S.C4H10O6S2
MW616.69
EINECS
MOL File200393-05-1.mol

Chemical Properties

InChIKey	GAODQEOSPBYWJE-YYOXXUFYNA-N
SMILES	C(OS(CCCCS(O)(=O)=O)(=O)=O)([S+](CC[C@H](N)C([O-])=O)C)[C@H]1O[C@@H](N2C3=C(C(=NC=N3)N)N=C2)C[C@@H]1O \|&1:16,22,24,36,r\|

Usage And Synthesis

Uses

S-Adenosyl-L-methionine (S-Adenosyl methionine) 1,4-butanedisulfonate is an orally active methyl group donor. S-Adenosyl-L-methionine 1,4-butanedisulfonate is a dietary supplement with potent antidepressant effects. S-Adenosyl-L-methionine 1,4-butanedisulfonate also has antiproliferative, proapoptotic and antimetastatic roles in cancers. S-Adenosyl-L-methionine 1,4-butanedisulfonate has the potential for, cancer, liver disease and osteoarthritis research[1][2][3].

in vivo

S-Adenosyl-L-methionine (30mg/kg, p.o., for 3 days) 1,4-butanedisulfonate prevents ASD like behaviors induced by early postnatal valproic acid exposure in young mice^[6].
S-Adenosyl-L-methionine (50 and 100 mg/kg, p.o.) 1,4-butanedisulfonate shows antiepileptic, memory-enhancing, and antioxidant properties in a Pentylenetetrazole-induced rat epilepsy model^[7].

Animal Model:	Valproic acid treated young mice^[6]
Dosage:	30mg/kg
Administration:	p.o., for 3 days
Result:	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. DOI:10.1111/j.1600-0404.1994.tb05403.x
[2] Wadie I Najm, et al. 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. DOI:10.1186/1471-2474-5-6
[3] Shelly C Lu, et al. S-adenosylmethionine in liver health, injury, and cancer. Physiol Rev. 2012 Oct;92(4):1515-42. DOI:10.1152/physrev.00047.2011
[4] Mosca L, et al. Effects of SadenosylLmethionine 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. DOI:10.3892/ijo.2020.5011
[5] Ham MS, et al. 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. DOI:10.3892/mco.2012.53
[6] Ornoy A, et al. 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. DOI:10.1016/j.ntt.2018.01.005
[7] Dhediya RM, et al. 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. DOI:10.1016/j.yebeh.2016.05.024

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