An active nucleoside metabolite of BMS-986094
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2′-C-β-Methylguanosine

Item No. 36548

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2′-C-methyl-guanosine
CAS Number
374750-30-8
Molecular Formula
C11H15N5O5
Formula Weight
297.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMSO: 1 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
255 nm
SMILES
C[C@@]1([C@](O[C@@H]([C@H]1O)CO)([H])N2C3=C(C(N=C(N3)N)=O)N=C2)O
InChi Code
InChI=1S/C11H15N5O5/c1-11(20)6(18)4(2-17)21-9(11)16-3-13-5-7(16)14-10(12)15-8(5)19/h3-4,6,9,17-18,20H,2H2,1H3,(H3,12,14,15,19)/t4-,6-,9-,11-/m1/s1
InChi Key
NVKAMPJSWMHVDK-GITKWUPZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    50 mg

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    Cayman Chemical
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    Product Description

    2’-C-β-Methylguanosine is an active nucleoside metabolite of the antiviral prodrug BMS-986094.1 It inhibits replication in genotype 1b hepatitis C virus (HCV) replicon cells (EC50s = 5.2 and 3.2 µM in ELISA and luciferase assays, respectively).2 2’-C-β-Methylguanosine also inhibits replication of the Zika virus clinical isolate ZIKVPE243 in infected human brain microvascular endothelial cells (HBMECs), SH-SY5Y cells, and Vero cells (EC50s = 0.88, 2.09, and 1.25 µM, respectively) but is toxic to mice infected with ZIKVPE243 at postnatal day 2 when administered at a dose of 25 mg/kg per day.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Liu, A., Lute, J., Gu, H., et al. Challenges and solutions in the bioanalysis of BMS-986094 and its metabolites including a highly polar, active nucleoside triphosphate in plasma and tissues using LC-MS/MS. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 1000, 29-40 (2015).

    2. Sizun, G., Pierra, C., Peyronnet, J., et al. Design, synthesis and antiviral evaluation of 2'-C-methyl branched guanosine pronucleotides: The discovery of IDX184, a potent liver-targeted HCV polymerase inhibitor. Future Med. Chem. 7(13), 1675-1700 (2015).

    3. Matos de Souza, M.R., Cunha, M.S., Okon, A., et al. In vitro and in vivo characterization of the anti-Zika virus activity of ProTides of 2'-C-β-methylguanosine. ACS Infect. Dis. 6(7), 1650-1658 (2020).