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5'-DEOXY-5'-METHYLTHIOADENOSINE

5'-DEOXY-5'-METHYLTHIOADENOSINE Structure
5'-DEOXY-5'-METHYLTHIOADENOSINE structure
CAS No.
2457-80-9
Chemical Name:
5'-DEOXY-5'-METHYLTHIOADENOSINE
Synonyms
MTA;Methylthioadenosine;Adenylthiomethylpentose;MESADO;Adenosyl Methionine Impurity 1;beta-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-;(2R,3R,4S,5S)-2-(6-Amino-9H-purin-9-yl)-5-((methylthio)methyl)tetrahydrofuran-3,4-diol;SKL060;NSC 335422;vitaminl(sub2)
CBNumber:
CB9392566
Molecular Formula:
C11H15N5O3S
Molecular Weight:
297.33
MDL Number:
MFCD00010533
MOL File:
2457-80-9.mol
Last updated:2024-04-26 17:21:34
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5'-DEOXY-5'-METHYLTHIOADENOSINE Properties

Melting point 210-213 °C (dec.)
Boiling point 642.7±65.0 °C(Predicted)
Density 1.85±0.1 g/cm3(Predicted)
storage temp. -20°C
solubility DMF (Sparingly), DMSO (Slightly), Methanol (Slightly)
pka 13.10±0.70(Predicted)
form White solid
color White to Off-White
BRN 42420
EWG's Food Scores 1
FDA UNII 634Z2VK3UQ

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319
Precautionary statements  P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Safety Statements  22-24/25
WGK Germany  3
RTECS  AU7410000
F  10-21
NFPA 704
0
2 0

5'-DEOXY-5'-METHYLTHIOADENOSINE price More Price(40)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich D5011 5?-Deoxy-5?-methylthioadenosine 2457-80-9 1g $1150 2024-03-01 Buy
Sigma-Aldrich 260585 5?-Deoxy-5?-methylthioadenosine 2457-80-9 50mg $144 2024-03-01 Buy
Cayman Chemical 15593 5?-Deoxy-5?-methylthioadenosine ≥99% 2457-80-9 25mg $41 2024-03-01 Buy
Cayman Chemical 15593 5?-Deoxy-5?-methylthioadenosine ≥99% 2457-80-9 50mg $78 2024-03-01 Buy
Sigma-Aldrich D5011 5?-Deoxy-5?-methylthioadenosine 2457-80-9 25mg $74.2 2024-03-01 Buy
Product number Packaging Price Buy
D5011 1g $1150 Buy
260585 50mg $144 Buy
15593 25mg $41 Buy
15593 50mg $78 Buy
D5011 25mg $74.2 Buy

5'-DEOXY-5'-METHYLTHIOADENOSINE Chemical Properties,Uses,Production

Uses

5′-Deoxy-5′-(methylthio)adenosine has been used as a protein methylation inhibitor to reduce E2F transcription factor 1 (E2F1) protein abundance in hepatocellular carcinoma (HCC) cells. It has also been used to inhibit histone methylation modification and study its role in hypoxia inducible factor-1 (Hif-1) nuclear transport.

Definition

ChEBI: Adenosine with the hydroxy group at C-5' substituted with a methylthio (methylsulfanyl) group.

Biological Activity

ki = 62 μm for s49-derived high-affinity camp phosphodiesterasemethylthioadenosine (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.

Biochem/physiol Actions

5′-Deoxy-5′-(methylthio)adenosine (Methylthioadenosine) may be used as a substrate to study the specificity and kinetics of 5′-methylthioadenosinephosphorylase (MTAP) (EC2.4.2.28), a tumor suppressor gene expressed enzyme that supports the S-adenosylmethionine (AdoMet) and methionine salvage pathways.

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].

Purification Methods

Recrystallise it from H2O and sublime it at 200o/0.004mm. [v.Euler & Myrb.ck Hoppe Seyler's Z physiol Chem 177 237 1928, Weygand & Trauth Chem Ber 84 633 1951, Baddiley et al. J Chem Soc 2662 1953.] The hydrochloride has m 161-162o [Kuhn & Henkel Hoppe Seyler's Z Physiol Chem 269 41 1941]. The picrate has m 183o(dec) (from H2O). [Beilstein 26 III/IV 3675.]

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.

5'-DEOXY-5'-METHYLTHIOADENOSINE synthesis

892-48-8
2457-80-9
Synthesis of 5'-DEOXY-5'-METHYLTHIOADENOSINE from 5'-CHLORO-5'-DEOXYADENOSINE

5'-DEOXY-5'-METHYLTHIOADENOSINE Preparation Products And Raw materials

Raw materials

Adenosine, 5'-S-methyl-2',3'-O-(1-methylethylidene)-5'-thio- (9CI) methylthioadenosine sulfoxide 5'-CHLORO-5'-DEOXYADENOSINE Sodium thiomethoxide Adenosine triphosphate

Preparation Products

5'-DEOXY-5'-METHYLTHIOADENOSINE Suppliers

Global( 134)Suppliers
Supplier Tel Email Country ProdList Advantage
Shanghai UCHEM Inc. 		+862156762820 +86-13564624040 sales@myuchem.com China 6710 58
Shanghai Daken Advanced Materials Co.,Ltd 		+86-371-66670886 info@dakenam.com China 15928 58
Henan Tianfu Chemical Co.,Ltd. 		+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21691 55
Hubei Jusheng Technology Co.,Ltd. 		18871490254 linda@hubeijusheng.com CHINA 28180 58
Shaanxi Pioneer Biotech Co., Ltd . 		+8613259417953 sales@pioneerbiotech.com China 3000 58
Standardpharm Co. Ltd. 		86-714-3992388 overseasales1@yongstandards.com United States 14336 58
TopScience Biochemical 		00852-68527855 info@itopbiochem.com China Hong Kong 902 58
career henan chemical co 		+86-0371-86658258 15093356674; factory@coreychem.com China 29826 58
Dideu Industries Group Limited 		+86-29-89586680 +86-15129568250 1026@dideu.com China 29220 58
BOC Sciences 		+16314854226 inquiry@bocsci.com United States 19743 58
Supplier Advantage
Shanghai UCHEM Inc. 		58
Shanghai Daken Advanced Materials Co.,Ltd 		58
Henan Tianfu Chemical Co.,Ltd. 		55
Hubei Jusheng Technology Co.,Ltd. 		58
Shaanxi Pioneer Biotech Co., Ltd . 		58
Standardpharm Co. Ltd. 		58
TopScience Biochemical 		58
career henan chemical co 		58
Dideu Industries Group Limited 		58
BOC Sciences 		58

View Lastest Price from 5'-DEOXY-5'-METHYLTHIOADENOSINE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Methyl-thioadenosine pictures 2024-04-26 Methyl-thioadenosine
2457-80-9
 US $0.00-0.00 / mg 10mg 0.98 10g ShenZhen H&D Pharmaceutical Technology Co., LTD
5'-S-Methyl-5'-thioadenosine pictures 2024-02-23 5'-S-Methyl-5'-thioadenosine
2457-80-9
 US $376.00-1719.00 / g 1g 0.98 10kh Shanghai UCHEM Inc.
Adenylthiomethylpentose pictures 2020-02-01 Adenylthiomethylpentose
2457-80-9
 US $1.00 / KG 1KG Min98% HPLC G/KG/TON Career Henan Chemical Co

5'-DEOXY-5'-METHYLTHIOADENOSINE Spectrum

5'-DEOXY-5'-METHYLTHIOADENOSINE(2457-80-9)1HNMR5'-DEOXY-5'-METHYLTHIOADENOSINE(2457-80-9)Raman

2457-80-9(5'-DEOXY-5'-METHYLTHIOADENOSINE)Related Search:

5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE S-ADENOSYL-L-METHIONINE IODIDE SALT 5'-ISOBUTYLTHIO-5'-DEOXYADENOSINE Adenosine S-ADENOSYL-L-METHIONINE
Ademetionine 1,4-butanedisulfonate 5'-DEOXY-5'-METHYLTHIOADENOSINE S-Adenosyl-L-methionine S-Adenosyl-5'-L-methionineSulfate,p-Toluenesulfonate S-ADENOSYL-L-METHIONINE CHLORIDE SALT
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2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol 7-(5-Methylthio-5-deoxy-D-ribofuranosyl)-7H-purine-6-amine 7-[Tetrahydro-3α,4α-dihydroxy-5β-(methylthiomethyl)furan-2-yl]-7H-purin-6-amine 5'-S-Methyl-5'-thioadesine 5'-Deoxy-5'-(methylthio)adenosine ,98% 1-(6-AMino-9H-purin 5'-Deoxy(Methylthio)adenosine NSC 335422 Adenosine, 5'-S-Methyl-5'-thio- 5'-Methylthioadenosine (VitaMin L2) 5'-(Methylthio)-5'-deoxyadenosine 5’-(methylthio)adenosine 5’-methylthioadenosine 5’-s-methyl-5’-thio-adenosin 5’-s-methylthioadenosine 5'-S-Methyl-5'-thioadenosine vitaminl(sub2) 5'-DEOXY-5'-METHYLTHIOADENOSINE 2,3-Dihydro-2-thioxo-9H-purin-6(1H)-one 5-Deoxy-5-methylthioadenosine - CAS 2457-80-9 - Calbiochem ′-S-Methyl-5′-thioadenosine Ademetionine 1,4-Butanedisulfonate Impurity 3 Methylthioadenosine reference substance 5'-DEOXY-5'-METHYLTHIOADENOSINE USP/EP/BP SKL060 MTA (2R,3R,4S,5S)-2-(6-Amino-9H-purin-9-yl)-5-((methylthio)methyl)tetrahydrofuran-3,4-diol beta-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio- Methylthioadenosine MESADO Adenylthiomethylpentose Adenosyl Methionine Impurity 1 13C5]-5'-deoxy-5'-methylthioadenosine 5'-DEOXY-5'-METHYLTHIOADENOSINE 2457-80-9 C11H15N5O3S C11H15N5O3S1 Nucleoside Analogs Nucleosides, Nucleotides, Oligonucleotides Biochemicals and Reagents BioChemical Biochemicals and Reagents Nucleoside Analogs Nucleosides, Nucleotides, Oligonucleotides