Tyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity.

Tiziana Bozzini (1) , Giorgia Botta (1) , Michela Delfino (1) , Silvano Onofri (1) , Raffaele Saladino (1) , Donatella Amatore (2) , Rossella Sgarbanti (3) , Lucia Nencioni (2) , Anna Teresa Palamara (2, 3)

1 Departmento of Ecology and Biology
2 Department of Public Health and Infectious Diseases
3 San Raffaele Pisana Scientific Institute for Resaearch

Catechol derivatives with lipophilic properties have been selectively synthesized by tyrosinase in high yield avoiding long and tedious protection/deprotection steps usually required in traditional procedures. The synthesis was effective also with immobilized tyrosinase able to perform for more runs. The novel catechols were evaluated against influenza A virus, that continue to represent a severe threat worldwide. A significant antiviral activity was observed in derivatives characterized by antioxidant activity and long carbon alkyl side-chains, suggesting the possibility of a new inhibition mechanism based on both redox and lipophilic properties.

Domaines: Biochimie, Biologie Moléculaire; Virologie

Tiziana Bozzini, Giorgia Botta, Michela Delfino, Silvano Onofri, Raffaele Saladino, et al.. Tyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity.. Bioorganic and Medicinal Chemistry, 2013, 21 (24), pp.7699-708. ⟨10.1016/j.bmc.2013.10.026⟩. ⟨pasteur-01049065⟩