title: Affinity of sulfamates and sulfamides to carbonic anhydrase II isoform: experimental and molecular modeling approaches.
abstract: Sixteen aromatic and aliphatic sulfamides and sulfamates were synthesized and tested in their inhibition to carbonic anhydrase CAII activity. The weaker inhibition pattern shown by sulfamides as compared to sulfamates is interpreted in this research by means of molecular modeling techniques, including known inhibitors (topiramate and its sulfamide cognate) in the analysis. The results nicely explain the origin of the inhibitory activity, which is not only related to positive interactions of the ligand with the active site residues but also to the solvation pattern characteristic of each ligand.
authors.affiliation: Medicinal Chemistry, Department of Biological Sciences, Faculty of Exact Sciences, National University of La Plata, 47 and 115, La Plata B1900BJW, Argentina. lgavernet@biol.unlp.edu.ar
authors.forename: Luciana
authors.initials: L
authors.lastname: Gavernet
authors.forename: Jose L
authors.initials: JL
authors.lastname: Gonzalez Funes
authors.forename: Luis Bruno
authors.initials: LB
authors.lastname: Blanch
authors.forename: Guillermina
authors.initials: G
authors.lastname: Estiu
authors.forename: Alfonso
authors.initials: A
authors.lastname: Maresca
authors.forename: Claudiu T
authors.initials: CT
authors.lastname: Supuran
mesh_terms: D024402:Carbonic Anhydrase II / Q000737:chemistry* / Q000378:metabolism*; D020134:Catalytic Domain; D007527:Isoenzymes / Q000737:chemistry / Q000378:metabolism; D008024:Ligands; D056004:Molecular Dynamics Simulation; D011485:Protein Binding; D012997:Solvents / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry / Q000378:metabolism*; D013451:Sulfonic Acids / Q000737:chemistry / Q000378:metabolism*; D014867:Water / Q000737:chemistry
chemical_list: D007527:Isoenzymes; D008024:Ligands; D012997:Solvents; D013449:Sulfonamides; D013451:Sulfonic Acids; D014867:Water; C005741:sulfamic acid; D024402:Carbonic Anhydrase II