ABSTRACT
Hydroxytyrosol and dihydrocaffeoyl catechols with lipophilic properties have been synthesized in high yield using tyrosinase immobilized on multi-walled carbon nanotubes by the Layer-by-Layer technique. All synthesized catechols were evaluated against a large panel of DNA and RNA viruses, including Poliovirus type 1, Echovirus type 9, Herpes simplex virus type 1 (HSV-1), Herpes simplex virus type 2 (HSV-2), Coxsackievirus type B3 (Cox B3), Adenovirus type 2 and type 5 and Cytomegalovirus (CMV). A significant antiviral activity was observed in the inhibition of HSV-1, HSV-2, Cox B3 and CMV. The mechanism of action of the most active dihydrocaffeoyl derivative was investigated against a model of HSV-1 infection.
Subject(s)
Antiviral Agents/chemistry , Antiviral Agents/pharmacology , Catechols/chemistry , Catechols/pharmacology , DNA Viruses/drug effects , RNA Viruses/drug effects , Agaricus/enzymology , DNA Virus Infections/drug therapy , Enzymes, Immobilized/chemistry , Humans , Models, Molecular , Monophenol Monooxygenase/chemistry , Nanotubes, Carbon/chemistry , Phenylethyl Alcohol/analogs & derivatives , Phenylethyl Alcohol/chemistry , Phenylethyl Alcohol/pharmacology , RNA Virus Infections/drug therapyABSTRACT
A series of modified N,O-nucleosides, characterized by the presence of a furopyrimidine moiety, has been synthesized by exploiting a Sonogashira cross coupling reaction of 1-isoxazolidinyl-5-iodouracil with alkynes, followed by treatment with CuI in refluxing TEA/MeOH mixture. The obtained compounds were screened against both RNA and DNA viruses. None of the compounds were endowed with antiviral activity at subtoxic concentrations. However, some of them were able to inhibit proliferation of MRC-5, Vero, BS-C-1 cells by 50% (CC50) at concentrations ranging from 0.7 to 62.5 mM.
