Synthesis of Stilbene and Chalcone Inhibitors of Influenza A Virus by SBA-15 Supported Hoveyda-Grubbs Metathesis

Abstract

Stilbene and chalcone derivatives with biological activity against influenza A virus have been synthesized by self-, cross-, and ring-closing metathesis procedures. The reactions were performed under environmentally friendly conditions using the second generation Hoveyda-Grubbs catalyst Aquamet SiPr after immobilization on Santa Barbara Amorphous mesoporous silicate SBA-15. Irrespective from the experimental conditions, the heterogeneous catalyst showed activity and selectivity comparable than the homogeneous counterpart for at least six successive runs without appreciable leaching of the active species. An appreciable antiviral activity against influenza A virus for some of the novel derivatives were observed, mainly involving the early stage of the virus-replication life-cycle.

Laccase-Catalyzed 1,4-Dioxane-Mediated Synthesis of Belladine N-Oxides with Anti-Influenza A Virus Activity

“…The influenza A virus ( Orthomyxoviridae family) is characterized by the release of eight viral RNA segments associated with the nucleoprotein (NP) and the viral RNA-dependent RNA polymerase (RdRp) complex responsible for replication and transcription cycles [ 45 ]. Among the inhibitors of the influenza A virus, the compounds active against NA received great attention being involved in the release of viral particles from infected cells [ 46 , 47 ]. In the first set of experiments, A549 cells infected with 0.001 MOI of PR8 were treated with different concentrations (range 10–40 mg/mL) of compounds 9 and 12a – h for 24 h. The expression of Hemagglutinin (HA) was analyzed by means of In Cell Western (ICW) assay (as described in the Materials and Methods section) on cell monolayers.…”

“…The ICW assay was performed using the Odyssey Imaging System (LI-COR, Lincoln, NE, USA) as previously described [ 47 ]. Briefly, A549 or MDCK cells grown in 96-well plates (2 × 10 4 cells/well), either infected or mock-infected (Ctr) with PR8, were fixed with 4% formaldehyde, washed, permeabilized with 0.1% Triton X-100 and incubated with PBS containing Odyssey Blocking buffer (LI-COR Biosciences, Lincoln, NE, USA).…”

Redox-Modulating Agents in the Treatment of Viral Infections

“…In this context, RV efficacy against influenza virus replication was not related to glutathione-mediated antioxidant activity [98], but rather to the inhibition of cellular kinases [4]. Furthermore, anti-influenza properties of stilbene and chalcone derivatives have been reported [99].…”

Investigation of Commiphora myrrha (Nees) Engl. Oil and Its Main Components for Antiviral Activity

“…E (1%). The expression of viral nucleoprotein (NP) was analyzed by ICW, a method that allows the evaluation of the expression of viral proteins directly on an infected monolayer [ 15 ]. As shown in Figure 3 , the expression of NP was significantly reduced using myrrh oil at 25 and 50 µg/mL in mixture with Vit.…”