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RSS FeedsIJMS, Vol. 20, Pages 6269: Less Cytotoxic Protoflavones as Antiviral Agents: Protoapigenone 1´-O-isopropyl ether Shows Improved Selectivity Against the Epstein-Barr Virus Lytic Cycle (International Journal of Molecular Sciences)

 
 

13 december 2019 05:02:34

 
IJMS, Vol. 20, Pages 6269: Less Cytotoxic Protoflavones as Antiviral Agents: Protoapigenone 1´-O-isopropyl ether Shows Improved Selectivity Against the Epstein-Barr Virus Lytic Cycle (International Journal of Molecular Sciences)
 


Protoflavones, a rare group of natural flavonoids with a non-aromatic B-ring, are best known for their antitumor properties. The protoflavone B-ring is a versatile moiety that might be explored for various pharmacological purposes, but the common cytotoxicity of these compounds is a limitation to such efforts. Protoapigenone was previously found to be active against the lytic cycle of Epstein–Barr virus (EBV). Further, the 5-hydroxyflavone moiety is a known pharmacophore against HIV-integrase. The aim of this work was to prepare a series of less cytotoxic protoflavone analogs and study their antiviral activity against HIV and EBV. Twenty-seven compounds, including 18 new derivatives, were prepared from apigenin through oxidative de-aromatization and subsequent continuous-flow hydrogenation, deuteration, and/or 4′-oxime formation. One compound was active against HIV at the micromolar range, and three compounds showed significant activity against the EBV lytic cycle at the medium-low nanomolar range. Among these derivatives, protoapigenone 1′-O-isopropyl ether (6) was identified as a promising lead that had a 73-times selectivity of antiviral over cytotoxic activity, which exceeds the selectivity of protoapigenone by 2.4-times. Our results open new opportunities for designing novel potent and safe anti-EBV agents that are based on the natural protoflavone moiety.


 
476 viewsCategory: Biochemistry, Biophysics, Molecular Biology
 
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