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2′-C-Methyladenosine (CAS 15397-12-3)

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Alternate Names:
2′-Methyl-adenosine
Application:
2′-C-Methyladenosine is an inhibitor of HCV RNA replication
CAS Number:
15397-12-3
Purity:
≥98%
Molecular Weight:
281.27
Molecular Formula:
C11H15N5O4
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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2′-C-Methyladenosine (2′-CMA) is a modified nucleoside present in eukaryotic mRNA, serving as a element in RNA metabolism, gene expression, and regulation. It represents a modified version of adenosine and is prevalent in the mRNA of various organisms, including humans. 2′-C-Methyladenosine assumes a significant role in gene expression regulation and contributes to cellular development and functionality by participating in diverse biochemical and physiological processes. Although the precise mechanism of action of 2′-C-Methyladenosine remains incompletely understood, it is believed to engage with ribosomes, thereby exerting influence on mRNA stability, translation, and splicing. Moreover, it is implicated in the regulation of protein synthesis and mRNA processing, augmenting its impact on gene expression regulation. In addition to its regulatory role, 2′-C-Methyladenosine has demonstrated the ability to impede HCV RNA replication without inducing cytotoxicity. In vitro experiments have revealed that the corresponding triphosphates act as potent, competitive inhibitors of NS5B-catalyzed reactions.


2′-C-Methyladenosine (CAS 15397-12-3) References

  1. Inhibition of hepatitis C virus RNA replication by 2'-modified nucleoside analogs.  |  Carroll, SS., et al. 2003. J Biol Chem. 278: 11979-84. PMID: 12554735
  2. Synthesis of 2-C-hydroxymethylribofuranosylpurines as potent anti-hepatitis C virus (HCV) agents.  |  Yoo, BN., et al. 2006. Bioorg Med Chem Lett. 16: 4190-4. PMID: 16781148
  3. Liver-targeted prodrugs of 2'-C-methyladenosine for therapy of hepatitis C virus infection.  |  Hecker, SJ., et al. 2007. J Med Chem. 50: 3891-6. PMID: 17636948
  4. N6-Cycloalkyl- and N6-bicycloalkyl-C5'(C2')-modified adenosine derivatives as high-affinity and selective agonists at the human A1 adenosine receptor with antinociceptive effects in mice.  |  Franchetti, P., et al. 2009. J Med Chem. 52: 2393-406. PMID: 19317449
  5. Nucleoside inhibitors of tick-borne encephalitis virus.  |  Eyer, L., et al. 2015. Antimicrob Agents Chemother. 59: 5483-93. PMID: 26124166
  6. Targeting mitochondrial RNA polymerase in acute myeloid leukemia.  |  Bralha, FN., et al. 2015. Oncotarget. 6: 37216-28. PMID: 26484416
  7. Evaluation of antivirals against tick-borne encephalitis virus in organotypic brain slices of rat cerebellum.  |  Lenz, N., et al. 2018. PLoS One. 13: e0205294. PMID: 30300398
  8. An E460D Substitution in the NS5 Protein of Tick-Borne Encephalitis Virus Confers Resistance to the Inhibitor Galidesivir (BCX4430) and Also Attenuates the Virus for Mice.  |  Eyer, L., et al. 2019. J Virol. 93: PMID: 31142664
  9. Development and characterization of recombinant tick-borne encephalitis virus expressing mCherry reporter protein: A new tool for high-throughput screening of antiviral compounds, and neutralizing antibody assays.  |  Haviernik, J., et al. 2021. Antiviral Res. 185: 104968. PMID: 33157129
  10. Elimination of LRVs Elicits Different Responses in Leishmania spp.  |  Saura, A., et al. 2022. mSphere. 7: e0033522. PMID: 35943162
  11. Efficient elimination of RNA mycoviruses in aspergillus species using RdRp-inhibitors ribavirin and 2'-C-methylribonucleoside derivatives.  |  Ikeda, A., et al. 2022. Front Microbiol. 13: 1024933. PMID: 36274709
  12. 2'-C-methyladenosine and 2'-C-methyluridine 5'-diphosphates are mechanism-based inhibitors of ribonucleoside diphosphate reductase from Corynebacterium nephridii.  |  Ong, SP., et al. 1993. Biochemistry. 32: 11397-404. PMID: 8218205
  13. Mechanism-based inhibition of ribonucleoside diphosphate reductase from Corynebacterium nephridii by 2'-C-methyladenosine diphosphate.  |  McFarlan, SC., et al. 1996. Biochemistry. 35: 4485-91. PMID: 8605198

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2′-C-Methyladenosine, 50 mg

sc-283467
50 mg
$204.00

2′-C-Methyladenosine, 100 mg

sc-283467A
100 mg
$380.00

2′-C-Methyladenosine, 1 g

sc-283467B
1 g
$662.00