Carbon- versus sulphur-based zinc binding groups for carbonic anhydrase inhibitors?

ABSTRACT: A set of compounds incorporating carbon-based zinc-binding groups (ZBGs), of the type PhX (X = COOH, CONH₂, CONHNH₂, CONHOH, CONHOMe), and the corresponding derivatives with sulphur(VI)-based ZBGs (X = SO₃H, SO₂NH₂, SO₂NHNH₂, SO₂NHOH, SO₂NHOMe) were tested as inhibitors of all mammalian isoforms of carbonic anhydrase (CA, EC 4.2.1.1), CA I-XV. Three factors connected with the ZBG influenced the efficacy as CA inhibitor (CAI) of the investigated compounds: (i) the pKa of the ZBG; (ii) its geometry (tetrahedral, i.e. sulphur-based, versus trigonal, i.e. carbon-based ZBGs), and (iii) orientation of the organic scaffold induced by the nature of the ZBG. Benzenesulphonamide was the best inhibitor

SUBMITTER: Supuran CT 

PROVIDER: S-EPMC6009921 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature