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

Leonardo E. RiafrechaLADECOR, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, La Plata, Argentina,

Daniela VulloLaboratorio di Chimica Bioinorganica, Universitá degli Studi di Firenze, Sesto Fiorentino (Firenze), Italy,

Safia Ouahrani-BettacheCentre d’Études d’Agents Pathogènes et Biotechnologies pour la Santé (CPBS), CNRS-Université Montpellier 1-Université Montpellier, Montpellier Cedex, France,

Stephan KöhlerCentre d’Études d’Agents Pathogènes et Biotechnologies pour la Santé (CPBS), CNRS-Université Montpellier 1-Université Montpellier, Montpellier Cedex, France,

Pascal DumyInstitut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS-ENSCM-UM1-UM2, Bâtiment de Recherche Max Mousseron, Ecole Nationale Supérieure de Chimie de Montpellier, Montpellier Cedex, France, and

Jean-Yves WinumInstitut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS-ENSCM-UM1-UM2, Bâtiment de Recherche Max Mousseron, Ecole Nationale Supérieure de Chimie de Montpellier, Montpellier Cedex, France, and

Claudiu T. SupuranLaboratorio di Chimica Bioinorganica, Universitá degli Studi di Firenze, Sesto Fiorentino (Firenze), Italy, ;NEUROFARBA Department, Section of Pharmaceutical Chemistry, Università degli Studi di Firenze, Sesto Fiorentino (Florence), Italy

Pedro A. ColinasLADECOR, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, La Plata, Argentina, Correspondence[email protected]

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Abstract

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.

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Declaration of interest

The authors report no declarations of interest.

This work was financed, in part, by an EU grant (Dynano) to CTS, CNRS/CNR (CoopIntEER program, grant no. 131999) to J-Y. W. and by UNLP and CONICET (Argentina). P. A. C. is member of the Scientific Research Career of CONICET.

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

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

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