5'-DEOXY-5'-METHYLTHIOADENOSINE

ChemicalBook > CAS DataBase List > 5'-DEOXY-5'-METHYLTHIOADENOSINE

5'-DEOXY-5'-METHYLTHIOADENOSINE

Product Name: 5'-DEOXY-5'-METHYLTHIOADENOSINE
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
Formula Weight: 297.33
MOL File: 2457-80-9.mol

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5'-DEOXY-5'-METHYLTHIOADENOSINE Property

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
biological source: synthetic (organic)
BRN: 42420

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Safety

Safety Statements: 22-24/25
WGK Germany: 3
RTECS: AU7410000
F: 10-21

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: D5011
Product name: 5?-Deoxy-5?-methylthioadenosine
Packaging: 1g
Price: $1150
Updated: 2024/03/01

Sigma-Aldrich

Product number: 260585
Product name: 5?-Deoxy-5?-methylthioadenosine
Packaging: 50mg
Price: $144
Updated: 2024/03/01

Cayman Chemical

Product number: 15593
Product name: 5?-Deoxy-5?-methylthioadenosine
Purity: ≥99%
Packaging: 25mg
Price: $41
Updated: 2024/03/01

Cayman Chemical

Product number: 15593
Product name: 5?-Deoxy-5?-methylthioadenosine
Purity: ≥99%
Packaging: 50mg
Price: $78
Updated: 2024/03/01

Sigma-Aldrich

Product number: D5011
Product name: 5?-Deoxy-5?-methylthioadenosine
Packaging: 25mg
Price: $74.2
Updated: 2024/03/01

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5'-DEOXY-5'-METHYLTHIOADENOSINE Chemical Properties,Usage,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 Preparation Products And Raw materials

Raw materials

Preparation Products

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5'-DEOXY-5'-METHYLTHIOADENOSINE Suppliers

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

Shanghai UCHEM Inc.

Product: 5'-S-Methyl-5'-thioadenosine 2457-80-9
Price: US $376.00-1719.00/g
Min. Order: 1g
Purity: 0.98
Supply Ability: 10kh
Release date: 2023-12-18

ShenZhen H&D Pharmaceutical Technology Co., LTD

Product: Methyl-thioadenosine 2457-80-9
Price: US $0.00-0.00/mg
Min. Order: 10mg
Purity: 0.98
Supply Ability: 10g
Release date: 2024-04-26

R&D Scientific Inc.

Product: 5'-Deoxy-5'-(methylthio)adenosine 2457-80-9
Price: US $1500.00/g
Min. Order: 1g
Purity: 98
Supply Ability: 500 Kg
Release date: 2024-05-28

2457-80-9, 5'-DEOXY-5'-METHYLTHIOADENOSINERelated 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 8-Aasm S-ADENOSYL-L-METHIONINE-D3 (S-METHYL-D3) TETRA(P-TOLUENESULFONATE) SALT S-ADENOSYL-L-METHIONINE, [METHYL-14C] Adenosine-5'-diphosphate disodium salt 5'-DEOXYADENOSINE SAENTA S-ADENOSYL-L-CYSTEINE ADENOSINE 5'-TRIPHOSPHATE DISODIUM SAL&

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-

2,3-Dihydro-2-thioxo-9H-purin-6(1H)-one

Adenylthiomethylpentose

5-Deoxy-5-methylthioadenosine - CAS 2457-80-9 - Calbiochem

′-S-Methyl-5′-thioadenosine

Ademetionine 1,4-Butanedisulfonate Impurity 3

MTA

Methylthioadenosine reference substance

5'-Methylthioadenosine (VitaMin L2)

(2R,3R,4S,5S)-2-(6-Amino-9H-purin-9-yl)-5-((methylthio)methyl)tetrahydrofuran-3,4-diol

5'-(Methylthio)-5'-deoxyadenosine

5’-(methylthio)adenosine

5’-methylthioadenosine

5’-s-methyl-5’-thio-adenosin

5’-s-methylthioadenosine

5'-S-Methyl-5'-thioadenosine

beta-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-

Methylthioadenosine

vitaminl(sub2)

5'-DEOXY-5'-METHYLTHIOADENOSINE

MESADO

Adenosyl Methionine Impurity 1

5'-DEOXY-5'-METHYLTHIOADENOSINE USP/EP/BP

SKL060

13C5]-5'-deoxy-5'-methylthioadenosine

5'-Methylthioadenosine

13C5]-5'-Deoxy-5'-methylthioadenosine([13C5]-MTA)

Methioadenosine

5''-Deoxy-5''-methylthioadenosine (Methylthioadenosine), Adenosine A1 receptor agonist

5''-Methylthioadenosine

2457-80-9

C11H15N5O3S

C11H15N5O3S1

Nucleoside Analogs

Nucleosides, Nucleotides, Oligonucleotides

Biochemicals and Reagents

BioChemical

Biochemicals and Reagents

Nucleoside Analogs

Nucleosides, Nucleotides, Oligonucleotides