7-Deaza-2’-C-methyladenosine

• CAT Number: R043334
• CAS Number: 443642-29-3
• Molecular Formula: C12H16N4O4
• Molecular Weight: 280.284
• Purity: ≥95%
• Synonyms: 7-(2-C-Methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine; MK 0608
• Storage: -20°C
• IUPAC Name: (2R,3R,4R,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol
• InChI: InChI=1S/C12H16N4O4/c1-12(19)8(18)7(4-17)20-11(12)16-3-2-6-9(13)14-5-15-10(6)16/h2-3,5,7-8,11,17-19H,4H2,1H3,(H2,13,14,15)/t7-,8-,11-,12-/m1/s1
• InChIKey: IRZRJANZDIOOIF-GAJNKVMBSA-N
• SMILES: CC1(C(C(OC1N2C=CC3=C2N=CN=C3N)CO)O)O

MK 0608 is an anti-viral agent against Hepatitis C Virus (HCV). It has been shown to inhibit viral RNA replication in the subgenomic HCV genotype 1b replicon, with a 50% effective concentration (EC50) of 0.3 μM (EC90 = 1.3 μM). To determine efficacy in vivo, MK-0608 was administered to HCV-infected chimpanzees, resulting in dose- and time-dependent decreases in plasma viral loads. In separate experiments, chimpanzees dosed for 7 days with MK-0608 at 0.2 and 2 mg per kg of body weight per day by intravenous administration experienced average reductions in viral load of 1.0 and >5 log10 IU/ml, respectively.

Reference

1:PLoS Negl Trop Dis. 2016 May 10;10(5):e0004695. doi: 10.1371/journal.pntd.0004695. eCollection 2016 May. The Viral Polymerase Inhibitor 7-Deaza-2/’-C-Methyladenosine Is a Potent Inhibitor of In Vitro Zika Virus Replication and Delays Disease Progression in a Robust Mouse Infection Model.Zmurko J,Marques RE,Schols D,Verbeken E,Kaptein SJ,Neyts J, PMID: 27163257 PMCID: PMC4862633 DOI: 10.1371/journal.pntd.0004695 Abstract: Zika virus (ZIKV) is an emerging flavivirus typically causing a dengue-like febrile illness, but neurological complications, such as microcephaly in newborns, have potentially been linked to this viral infection. We established a panel of in vitro assays to allow the identification of ZIKV inhibitors and demonstrate that the viral polymerase inhibitor 7-deaza-2/’-C-methyladenosine (7DMA) efficiently inhibits replication. Infection of AG129 (IFN-α/β and IFN-γ receptor knock-out) mice with ZIKV resulted in acute neutrophilic encephalitis with viral antigens accumulating in neurons of the brain and spinal cord. Additionally, high levels of viral RNA were detected in the spleen, liver and kidney, and levels of IFN-γ and IL-18 were systematically increased in serum of ZIKV-infected mice. Interestingly, the virus was also detected in testicles of infected mice. In line with its in vitro anti-ZIKV activity, 7DMA reduced viremia and delayed virus-induced morbidity and mortality in infected mice, which also validates this small animal model to assess the in vivo efficacy of novel ZIKV inhibitors. Since AG129 mice can generate an antibody response, and have been used in dengue vaccine studies, the model can also be used to assess the efficacy of ZIKV vaccines.  .