A natural derivative of SAM
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Labeled Version(s)
278365'-Deoxy-5'-methylthioadenosine-d3
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5'-Deoxy-5'-methylthioadenosine

Item No. 15593

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5'-S-methyl-5'-thio-adenosine
CAS Number
2457-80-9
Synonyms
  • 5'-S-Methylthioadenosine
  • MTA
  • NSC 335422
  • Vitamin L2
Molecular Formula
C11H15N5O3S
Formula Weight
297.3
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 20 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
260 nm
SMILES
NC1=NC=NC2=C1N=CN2[C@H]3[C@H](O)[C@H](O)[C@@H](CSC)O3
InChi Code
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
InChi Key
WUUGFSXJNOTRMR-IOSLPCCCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    25 mg

    $46

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    50 mg

    $86

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    100 mg

    $145

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    Product Description

    5'-Deoxy-5'-methylthioadenosine (MTA) is an intermediate in the generation of adenine and methionine that is produced by the decarboxylation of S-adenosylmethionine.1 This nucleoside is a potent agonist of adenosine receptors (Kis = 0.15, 1.13, 13.9, and 0.68 μM for A1, A2A, A2B, and A3, respectively).2 At higher concentrations, MTA inhibits several enzymes, including protein carboxylmethyltransferase (Ki = 41 μM), S-adenosylhomocysteine hydrolase, SET methyltransferases, and spermidine and spermine synthases.3,1,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Huang, S. Histone methyltransferases, diet nutrients and tumour suppressors. Nat. Rev. Cancer 2(6), 469-476 (2002).

    2. Kehraus, S., Gorzalka, S., Hallmen, C., et al. Novel amino acid derived natural products from the ascidian Atriolum robustum: Identification and pharmacological characterization of a unique adenosine derivative. J. Med. Chem. 47(9), 2243-2255 (2004).

    3. Oliva, A., Galletti, P., Zappia, V., et al. Studies on substrate specificity of S-adenosylmethionine: Protein-carboxyl methyltransferase from calf brain. Eur. J. Biochem. 104(2), 595-602 (1980).

    4. Cole, P.A. Chemical probes for histone-modifying enzymes. Nat. Chem. Biol. 4(10), 590-597 (2008).

    5. Lee, S.H., and Cho, Y.D. Induction of apoptosis in leukemia U937 cells by 5'-deoxy-5'-methylthioadenosine, a potent inhibitor of protein carboxylmethyltransferase. Exp. Cell Res. 240(2), 282-292 (1998).