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Methylthioadenosine sulfur-containing nucleoside

Catalog No.B6080
Size Price Stock Qty
50mg
$76.00
In stock
100mg
$127.00
In stock

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Sample solution is provided at 25 µL, 10mM.

Quality Control

Quality Control & MSDS

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Chemical structure

Methylthioadenosine

Methylthioadenosine Dilution Calculator

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Chemical Properties

Cas No. 2457-80-9 SDF Download SDF
Chemical Name (2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-((methylthio)methyl)tetrahydrofuran-3,4-diol
Canonical SMILES CSC[[email protected]](O1)([H])[[email protected]](O)([H])[[email protected]](O)([H])[[email protected]]1([H])N2C=NC(C2=NC=N3)=C3N
Formula C11H15N5O3S M.Wt 297.33
Solubility ≥83.3mg/mL in DMSO with gentle warming Storage Store at -20°C
Physical Appearance A white to off-white solid Shipping Condition Evaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Background

Ki = 62 μM for S49-derived high-affinity cAMP phosphodiesterase

Methylthioadenosine (MTA) is a naturally occurring sulfur-containing nucleoside in all mammalian tissues. MTA is mainly produced from S-adenosylmethionine via the polyamine biosynthetic pathway, behaving as a powerful inhibitory product.

In vitro: MTA was found to be solely metabolized by MTA-phosphorylase, to yield 5-methylthioribose-1-phosphate and adenine, which was a key step in methionine and purine salvage pathways, respectively. Previous studies suggested that MTA coud affect various cellular processes. MTA had been shown to be albe to influence plenty of critical cell responses, such as proliferation, gene expression regulation, differentiation as well as apoptosis. Though most of such responses had been only observed at the pharmacological level, their specificity made it tempting to speculate that endogenous MTA might play a regulatory role in the cell [1].

In vivo: The hepatoprotective effects of MTA had been evaluated in a model of CCl4-induced chronic liver damage in rats. In this study, MTA could reproduce the human lesions induced by alcohol and viral infections of the liver. In addition, replenishment of the hepatic pool of MTA showed strong anti-oxidant effects and also reduced liver cell damage and fibrosis [2].

Clinical trial: Up to now, MTA is still in the preclinical development stage.

References:
[1] Avila MA,García-Trevijano ER,Lu SC,Corrales FJ,Mato JM.  Methylthioadenosine. Int J Biochem Cell Biol.2004 Nov;36(11):2125-30.
[2] Pascale RM,Simile MM,De Miglio MR,Feo F.  Chemoprevention of hepatocarcinogenesis: S-adenosyl-L-methionine. Alcohol.2002 Jul;27(3):193-8.