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5'-DEOXY-5'-METHYLTHIOADENOSINE

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:2024-11-19 23:02:33

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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)

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

RTECS

AU7410000

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

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( 146)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Shanghai UCHEM Inc.	+862156762820 +86-13564624040	sales@myuchem.com	China	7514	58
Shanghai Daken Advanced Materials Co.,Ltd	+86-371-66670886	info@dakenam.com	China	18775	58
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21634	55
Hubei Jusheng Technology Co.,Ltd.	18871490254	linda@hubeijusheng.com	CHINA	28172	58
Shaanxi Pioneer Biotech Co., Ltd .	+8613259417953	sales@pioneerbiotech.com	China	3000	58
Standardpharm Co. Ltd.	86-714-3992388	overseasales1@yongstandards.com	United States	14332	58
TopScience Biochemical	00852-68527855	info@itopbiochem.com	China Hong Kong	902	58
career henan chemical co	+86-0371-86658258 +8613203830695	factory@coreychem.com	China	29811	58
TargetMol Chemicals Inc.	+1-781-999-5354 +1-00000000000	marketing@targetmol.com	United States	32165	58
Dideu Industries Group Limited	+86-29-89586680 +86-15129568250	1026@dideu.com	China	22783	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
TargetMol Chemicals Inc.	58
Dideu Industries Group Limited	58

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

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2024-11-19	5'-Methylthioadenosine 2457-80-9	US $39.00-57.00 / mg		99.32%	10g	TargetMol Chemicals Inc.
2024-11-01	5'-S-Methyl-5'-thioadenosine 2457-80-9	US $376.00-1719.00 / g	1g	0.98	10kh	Shanghai UCHEM Inc.
2024-09-20	Methyl-thioadenosine 2457-80-9	US $0.00-0.00 / mg	10mg	0.98	10g	ShenZhen H&D Pharmaceutical Technology Co., LTD

5'-Methylthioadenosine
2457-80-9
US $39.00-57.00 / mg
99.32%
TargetMol Chemicals Inc.

5'-S-Methyl-5'-thioadenosine
2457-80-9
US $376.00-1719.00 / g
0.98
Shanghai UCHEM Inc.

Methyl-thioadenosine
2457-80-9
US $0.00-0.00 / mg
0.98
ShenZhen H&D Pharmaceutical Technology Co., LTD

5'-DEOXY-5'-METHYLTHIOADENOSINE Spectrum

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

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

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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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SAENTA S-ADENOSYL-L-CYSTEINE ADENOSINE 5'-TRIPHOSPHATE DISODIUM SAL&

1of4

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 5'-Methylthioadenosine 13C5]-5'-Deoxy-5'-methylthioadenosine([13C5]-MTA) 5'-S-Methyl-5'-Thioadenosine 2457-80-9 C11H15N5O3S C11H15N5O3S1 Nucleoside Analogs Nucleosides, Nucleotides, Oligonucleotides Biochemicals and Reagents BioChemical Biochemicals and Reagents Nucleoside Analogs Nucleosides, Nucleotides, Oligonucleotides