5prime-Deoxy-5prime-methylthioadenosine CAS: 2457-80-9
MF: C11H15N5O3S
MW: 297.33
An endogenous methylthioadenosine phosphorylase substrate and potent inhibitor of PDE.

5′-Deoxy-5′-methylthioadenosine (CAS 2457-80-9)

5′-Deoxy-5′-methylthioadenosine | CAS 2457-80-9 is rated 5.0 out of 5 by 1.
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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 (including water content).

5′-Deoxy-5′-methylthioadenosine (MTA) has been shown 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 MTA-treated cells display an arrest in the M phase of the cell cycle. Other data suggest that MTA 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.


References

1. Riscoe, M.K., et al. 1984. Biochem. Pharmacol. 33: 3639-3643. PMID: 6095857
2. Munshi, R., et al. 1988. Biochem. Pharmacol. 37: 2085-2089. PMID: 3377811
3. Smalheiser, N.R. 1989. Brain Res. Dev. Brain Res. 45: 59-67. PMID: 2917413
4. Lee, S.H. and Cho, Y.D. 1998. Exp. Cell Res. 240: 282-292. PMID: 9597001

Physical State :
Solid
Solubility :
Soluble in DMF (25 mg/ml), DMSO, pyridine, and water (partly miscible).
Storage :
Store at -20° C
Melting Point :
208-209° C
Boiling Point :
642.70° C at 760 mmHg (Predicted)
Density :
1.85 g/cm3 (Predicted)
Refractive Index :
n20D 1.84 (Predicted)
IC50 :
Adenosine A1 receptor: IC50 = 680 nM (Rattus norvegicus); Adenosine A3 receptor: IC50 = 71 µM (human)
Ki Data :
Adenosine A1 receptor: Ki= 150 nM (Rattus norvegicus)
pK Values :
pKa: 13.10 (Predicted), pKb: 3.82 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
AU7410000
PubChem CID :
439176
MDL Number :
MFCD00010533
Beilstein Registry :
42420
SMILES :
CSCC1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)O

Download SDS (MSDS)

Certificate of Analysis

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Rated 5 out of 5 by from Lee Lee, SH. et al. (PubMed 9597001) reported that 5 -Deoxy-5 -methylthioadenosine, a potent inhibitor of PDE, induced apoptosis in leukemia U937 cells. -SCBT Publication Review
Date published: 2015-06-11
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