Antiviral activity and interaction mechanisms study of novel glucopyranoside derivatives.

Novel glucopyranoside derivatives were synthesized and evaluated for their antiviral activities against tobacco mosaic virus (TMV). Bioassay results indicated that some of the target compounds exhibited good in vivo antiviral activities against TMV. Among the title compounds, f6 showed appreciable inactivation effect against TMV, with the 50% effective concentration value (EC50) of 52.9 μg/mL, which was better than that of ribavirin (145.1 μg/mL). In addition, interaction between f6 and TMV-CP was characterized by fluorescence spectroscopy, isothermal titration calorimetry (ITC), and microscale thermophoresis (MST). Results showed that f6 bound to TMV-CP with micromole affinity, and thermodynamic parameters suggested that this interaction was typically endothermic and spontaneous, with 1:1.53 ratio of TMV-CP to f6. Thus, the synthesized glucopyranoside derivatives containing 1,4-pentadien-3-one moiety could be promising antiviral agents.