Inhibition of β -carbonic anhydrases from Brucella suis with C -cinnamoyl glycosides incorporating the phenol moiety

Leonardo Riafrecha (1) , Daniela Vullo (2) , Safia Ouahrani-Bettache (3) , Stephan Köhler (4) , Pascal Dumy (5, 6) , Jean-Yves Winum (6) , Claudiu T. Supuran (2) , Pedro Colinas (1)

1 UNLP - Universidad Nacional de la Plata [Argentine]
2 LCBI-UniFI - Laboratorio di Chimica Bioinorganica [UniFI, Firenze] = Laboratory of Bioinorganic Chemistry [UniFI Florence]
3 CPBS - Centre d’études d’Agents Pathogènes et Biotechologies pour la Santé
4 IRIM - Institut de Recherche en Infectiologie de Montpellier
5 LEDSS - Laboratoire d'études dynamiques et structurales de la sélectivité
6 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]

A small series of C-glycosides containing the phenol moiety was tested for the inhibition of the β-class carbonic anhydrases (βCAs, EC 4.2.1.1) from Brucella suis. Many compounds showed activities in the micromolar or submicromolar range and excellent selectivity for pathogen CAs over human isozymes. Glycosides incorporating the 3-hydroxyphenyl moiety showed the best inhibition profile, and therefore this functionality represents lead for the development of novel anti-infectives with a new mechanism of action.

Mots clés: Antibacterial; carbohydrate; carbonic anhydrase

Domaines: Chimie; Chimie organique

Leonardo Riafrecha, Daniela Vullo, Safia Ouahrani-Bettache, Stephan Köhler, Pascal Dumy, et al.. Inhibition of β -carbonic anhydrases from Brucella suis with C -cinnamoyl glycosides incorporating the phenol moiety. Journal of Enzyme Inhibition and Medicinal Chemistry, 2014, 30 (6), pp.1017-1020. ⟨10.3109/14756366.2014.986120⟩. ⟨hal-02425101⟩