Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C11H15N5O3S |
| Molecular Weight | 297.334 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=NC3=C2N=CN=C3N
InChI
InChIKey=WUUGFSXJNOTRMR-IOSLPCCCSA-N
InChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1
| Molecular Formula | C11H15N5O3S |
| Molecular Weight | 297.334 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20529342
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20529342
5'-Methylthioadenosine, also known as methylthioadenosine or MTA, is a naturally occurring sulfur-containing nucleoside present in all mammalian tissues. MTA is produced from S-adenosylmethionine mainly through the polyamine biosynthetic pathway, where it behaves as a powerful inhibitory product. This compound is metabolized solely by 5'-methylthioadenosine phosphorylase (MTAP), to yield 5-methylthioribose-1-phosphate and adenine, a crucial step in the methionine and purine salvage pathways, respectively. MTA has been shown to influence numerous critical responses of the cell including regulation of gene expression, proliferation, differentiation and apoptosis. Also was shown that MTA inhibits melanoma cell proliferation and in vivo tumor growth particularly in BRAF mutant melanoma cells. These data reveal a naturally occurring drug potentially useful for melanoma treatment.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| S-adenosylmethionine inhibits lipopolysaccharide-induced gene expression via modulation of histone methylation. | 2008-05 |
|
| Redox regulation of methylthioadenosine phosphorylase in liver cells: molecular mechanism and functional implications. | 2008-04-15 |
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| Losses of 3p14 and 9p21 as shown by fluorescence in situ hybridization are early events in tumorigenesis of oral squamous cell carcinoma and already occur in simple keratosis. | 2008-04 |
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| Azetidine based transition state analogue inhibitors of N-ribosyl hydrolases and phosphorylases. | 2008-02-28 |
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| Leptin's mitogenic effect in human liver cancer cells requires induction of both methionine adenosyltransferase 2A and 2beta. | 2008-02 |
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| S-adenosylmethionine and its products. | 2008-02 |
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| Enzymes as a special class of therapeutic target: clinical drugs and modes of action. | 2007-12 |
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| Metabolic signature of breast cancer cell line MCF-7: profiling of modified nucleosides via LC-IT MS coupling. | 2007-11-29 |
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| Protein arginine methyltransferase 1: positively charged residues in substrate peptides distal to the site of methylation are important for substrate binding and catalysis. | 2007-11-20 |
|
| Methylthioadenosine phosphorylase deficiency in Japanese osteosarcoma patients. | 2007-11 |
|
| Nicotinamide riboside kinase structures reveal new pathways to NAD+. | 2007-10-02 |
|
| The complete genome sequence of Yersinia pseudotuberculosis IP31758, the causative agent of Far East scarlet-like fever. | 2007-08 |
|
| Methylthioadenosine phosphorylase (MTAP) in hearing: gene disruption by chromosomal rearrangement in a hearing impaired individual and model organism analysis. | 2007-07-15 |
|
| Role of methionine adenosyltransferase 2A and S-adenosylmethionine in mitogen-induced growth of human colon cancer cells. | 2007-07 |
|
| Update on chondrosarcomas. | 2007-07 |
|
| A potential predictive marker for response to interferon in malignant melanoma. | 2007-06 |
|
| Role of S-adenosyl-L-methionine in liver health and injury. | 2007-05 |
|
| A novel approach for determining cancer genomic breakpoints in the presence of normal DNA. | 2007-04-18 |
|
| Polymeric nanoparticle-encapsulated curcumin ("nanocurcumin"): a novel strategy for human cancer therapy. | 2007-04-17 |
|
| [Regulation of methionine/cysteine biosynthesis in Corynebacterium glutamicum and related genomes]. | 2007-03-27 |
|
| Inhibition of human betaine-homocysteine methyltransferase expression by S-adenosylmethionine and methylthioadenosine. | 2007-01-01 |
|
| The role of methionine recycling for ethylene synthesis in Arabidopsis. | 2007-01 |
|
| Growth control of the eukaryote cell: a systems biology study in yeast. | 2007 |
|
| Comparative protein modeling of spermidine synthase from Plasmodium falciparum: A potential target for anti-malarial drug therapy. | 2006-12-23 |
|
| The complete genome sequence and comparative genome analysis of the high pathogenicity Yersinia enterocolitica strain 8081. | 2006-12-15 |
|
| S-adenosylmethionine or 5'-methylthioadenosine are unable to prevent fumonisin B1 hepatotoxicity in mice despite increased oxidation in liver. | 2006-11-03 |
|
| The effect of a novel transition state inhibitor of methylthioadenosine phosphorylase on pemetrexed activity. | 2006-10 |
|
| The methionine salvage pathway compound 4-methylthio-2-oxobutanate causes apoptosis independent of down-regulation of ornithine decarboxylase. | 2006-09-28 |
|
| Toxoplasma gondii purine nucleoside phosphorylase biochemical characterization, inhibitor profiles, and comparison with the Plasmodium falciparum ortholog. | 2006-09-01 |
|
| Methylthioadenosine reverses brain autoimmune disease. | 2006-09 |
|
| The prognostic significance of CDKN2A, CDKN2B and MTAP inactivation in B-lineage acute lymphoblastic leukemia of childhood. Results of the EORTC studies 58881 and 58951. | 2006-07 |
|
| Histone H3 lysine 4 dimethylation signals the transcriptional competence of the adiponectin promoter in preadipocytes. | 2006-06-23 |
|
| Lack of methylthioadenosine phosphorylase expression in mantle cell lymphoma is associated with shorter survival: implications for a potential targeted therapy. | 2006-06-15 |
|
| Differential regulation of the JNK/AP-1 pathway by S-adenosylmethionine and methylthioadenosine in primary rat hepatocytes versus HuH7 hepatoma cells. | 2006-06 |
|
| Methylthioadenosine and polyamine biosynthesis in a Saccharomyces cerevisiae meu1delta mutant. | 2006-04-28 |
|
| Methylthioadenosine phosphorylase gene deletions are frequently detected by fluorescence in situ hybridization in conventional chondrosarcomas. | 2006-04-15 |
|
| Development of high-throughput spermidine synthase activity assay using homogeneous time-resolved fluorescence. | 2006-04-15 |
|
| Fine-mapping loss of gene architecture at the CDKN2B (p15INK4b), CDKN2A (p14ARF, p16INK4a), and MTAP genes in head and neck squamous cell carcinoma. | 2006-04 |
|
| Tissue microarray analysis of methylthioadenosine phosphorylase protein expression in melanocytic skin tumors. | 2006-04 |
|
| EFA (9-beta-D-erythrofuranosyladenine) is an effective salvage agent for methylthioadenosine phosphorylase-selective therapy of T-cell acute lymphoblastic leukemia with L-alanosine. | 2006-02-01 |
|
| Circadian pharmacology of L-alanosine (SDX-102) in mice. | 2006-02 |
|
| Promoter-hypermethylation is causing functional relevant downregulation of methylthioadenosine phosphorylase (MTAP) expression in hepatocellular carcinoma. | 2006-01 |
|
| Homozygous deletions of methylthioadenosine phosphorylase in human biliary tract cancers. | 2005-12 |
|
| Concordant loss of MTAP and p16/CDKN2A expression in gastroesophageal carcinogenesis: evidence of homozygous deletion in esophageal noninvasive precursor lesions and therapeutic implications. | 2005-11 |
|
| Natural history of S-adenosylmethionine-binding proteins. | 2005-10-14 |
|
| Comparative analysis of RNA regulatory elements of amino acid metabolism genes in Actinobacteria. | 2005-10-03 |
|
| S-adenosylmethionine blocks collagen I production by preventing transforming growth factor-beta induction of the COL1A2 promoter. | 2005-09-02 |
|
| Design and evaluation of 5'-modified nucleoside analogs as prodrugs for an E. coli purine nucleoside phosphorylase mutant. | 2005 |
|
| Methylthioadenosine. | 2004-11 |
|
| Antimicrobial and antiviral activity of xylosyl-methylthio-adenosine, a naturally occurring analogue of methylthio-adenosine from Doris verrucosa. | 1991-12-01 |
Sample Use Guides
In liver damage experiment 5-Methylthioadenosine was given intramuscularly four daily doses (96 mmol/kg each).
Route of Administration:
Intramuscular
The standard reaction mixture contained for an assay of spermine synthase activity was performed. A reaction mixture contained in a total volume of 0.1 mL, 20 pM 14C-labeled S-methyladenosylhomocysteamine, 1 mM spermidine, 5 mM dithiothreitol, 0.05 mg of enzyme protein, inhibitors at concentrations of 0.01-1.0 mM, and 0.1 M potassium phosphate buffer (pH 7.4). The mixture was incubated at 37 °C for 20 min, and the reaction was stopped by the addition of 10 pL of 1 M potassium hydroxide. 5-Methylthioadenosine inhibited spermine synthase with IC50 < 100 uM.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 20:13:37 GMT 2025
by
admin
on
Mon Mar 31 20:13:37 GMT 2025
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| Record UNII |
634Z2VK3UQ
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| Record Status |
Validated (UNII)
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| Record Version |
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DB02282
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5?-Methylthioadenosine
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C008500
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335422
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634Z2VK3UQ
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DTXSID20179308
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2457-80-9
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17509
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| Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE |
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TARGET -> INHIBITOR |
MTA competes with the activating cofactor S-adenosyl-l-methionine (SAM), causing a decrease in PRMT5 activity and sensitizes the MTAP-del cells to further loss of PRMT5 activity.
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| Related Record | Type | Details | ||
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PARENT -> METABOLITE |
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