Molecular structure of 5′-Deoxy-5′-methylthioadenosine, CAS Number: 2457-80-9
5′-Deoxy-5′-methylthioadenosine (CAS 2457-80-9)
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Alternate Names:
5′-Deoxy-5′-(methylthio)-D-adenosine; 5′-(Methylthio)-5′-deoxyadenosine
Application:
5′-Deoxy-5′-methylthioadenosine is an endogenous methylthioadenosine phosphorylase substrate and potent inhibitor of PDE
CAS Number:
2457-80-9
Purity:
≥98%
Molecular Weight:
297.33
Molecular Formula:
C11H15N5O3S
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
5′-Deoxy-5′-methylthioadenosine (MTA) may act to be a potent inhibitor of protein carboxylmethyltransferase and a naturally occurring co-product of polyamine biosynthesis. This nucleoside has been reported to potently inhibit the growth of certain cells by causing apoptosis. Treatment of cells with this compound has caused inhibition of cAMP phosphodiesterase which subsequently increases cAMP levels resulting in cell growth arrest. More specific studies demonstrate that 5′-Deoxy-5′-methylthioadenosine-treated cells display an arrest in the M phase of the cell cycle. Other data suggest that 5′-Deoxy-5′-methylthioadenosine displays agonist and antagonist characteristics towards adenosine A1-receptor (adenosine A1-R) and Adenosine A2-R, respectively. 5′-Deoxy-5′-methylthioadenosine is a substrate of 5′-methylthioadenosinephosphorylase (MTAP), an enzyme known to be expressed by tumor suppressor genes.
5′-Deoxy-5′-methylthioadenosine (CAS 2457-80-9) References
- Three-dimensional structure of a hyperthermophilic 5'-deoxy-5'-methylthioadenosine phosphorylase from Sulfolobus solfataricus. | Appleby, TC., et al. 2001. J Biol Chem. 276: 39232-42. PMID: 11489901
- Purification and characterization of 5'-deoxy-5'-methylthioadenosine (MTA) phosphorylase from human liver. | Toorchen, D. and Miller, RL. 1991. Biochem Pharmacol. 41: 2023-30. PMID: 1903946
- Down-regulation of methylthioadenosine phosphorylase (MTAP) induces progression of hepatocellular carcinoma via accumulation of 5'-deoxy-5'-methylthioadenosine (MTA). | Kirovski, G., et al. 2011. Am J Pathol. 178: 1145-52. PMID: 21356366
- Differential neuroprotective effects of 5'-deoxy-5'-methylthioadenosine. | Moreno, B., et al. 2014. PLoS One. 9: e90671. PMID: 24599318
- Suppressive effects of tumor cell-derived 5'-deoxy-5'-methylthioadenosine on human T cells. | Henrich, FC., et al. 2016. Oncoimmunology. 5: e1184802. PMID: 27622058
- Altered cell shapes in fibroblasts treated with 5'-deoxy-5'-methylthioadenosine: relation to morphogenesis of neural cells. | Smalheiser, NR. 1989. Brain Res Dev Brain Res. 45: 59-67. PMID: 2917413
- Human 5'-deoxy-5'-methylthioadenosine phosphorylase: kinetic studies and catalytic mechanism. | Zappia, V., et al. 1988. Adv Exp Med Biol. 250: 165-77. PMID: 3151224
- The Oncometabolite 5'-Deoxy-5'-Methylthioadenosine Blocks Multiple Signaling Pathways of NK Cell Activation. | Jacobs, B., et al. 2020. Front Immunol. 11: 2128. PMID: 33123121
- 5'-Deoxy-5'-methylthioadenosine: a nucleoside which differentiates between adenosine receptor types. | Munshi, R., et al. 1988. Biochem Pharmacol. 37: 2085-9. PMID: 3377811
- Mechanism of action of 5'-methylthioadenosine in S49 cells. | Riscoe, MK., et al. 1984. Biochem Pharmacol. 33: 3639-43. PMID: 6095857
- Inactivation of S-adenosylhomocysteine hydrolase by 5'-deoxy-5'-methylthioadenosine. | Ferro, AJ., et al. 1981. Biochem Biophys Res Commun. 100: 523-31. PMID: 6791639
- Trends in the biochemical pharmacology of 5'-deoxy-5'-methylthioadenosine. | Williams-Ashman, HG., et al. 1982. Biochem Pharmacol. 31: 277-88. PMID: 6803807
- NGF protects PC12 cells against ischemia by a mechanism that requires the N-kinase. | Boniece, IR. and Wagner, JA. 1995. J Neurosci Res. 40: 1-9. PMID: 7714916
- 5'-Deoxy-5'-methylthioadenosine phosphorylase and p16INK4 deficiency in multiple tumor cell lines. | Della Ragione, F., et al. 1995. Oncogene. 10: 827-33. PMID: 7898924
- Induction of apoptosis in leukemia U937 cells by 5'-deoxy-5'-methylthioadenosine, a potent inhibitor of protein carboxylmethyltransferase. | Lee, SH. and Cho, YD. 1998. Exp Cell Res. 240: 282-92. PMID: 9597001
Inhibitor of:
Adenosine A2A-R, Adenosine A2B-R, AK8, APIP, C4ST-1, C9orf41, CD15s, CXorf34, EBP1, FTSJ1, FTSJ3, HBO1, HEMK2, IDI2, JMJD2C, JMJD3, JMJD8, KIAA1429, kynureninase, LCMT1, MAT IIα, Mat1, METT10D, METT11D1, METTL12, METTL2, METTL22, METTL2B, METTL9, MRS2p, NNMT, NSUN5, NSUN7, Olfr871, PCMT1, PDE, PME-1, PRMT7, RG9MTD3, RNMT, SAHH-3, SATB1, SET7/9, SETD2, SETD4, SMYD1, St3Gal-I, TETRAN, TNAP, TRM61, TRMT5, ZC3H13, and ZXDC.Activator of:
γ-GCSc, ADAT1, Adenosine A1-R, adenosine deaminase, AHCYL2, ALKBH8, ARD, Dimethyl Histone H3, Edc4, Histone cluster 2 H2AA3, HP1, HTF9C, LIN-53, MAT Iα, MAT IIβ, ODC, PIG-S, Pneumolysin, PRMT1, PRMT8, and TRMT1.Substrate of:
MTAP.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
5′-Deoxy-5′-methylthioadenosine, 50 mg | sc-202427 | 50 mg | $122.00 |