Saccharin Inhibits Carbonic Anhydrases: Possible Explanation for its Unpleasant Metallic Aftertaste

Abstract

A matter of taste: The sweetner saccharin (a cyclic sulfimide, see picture) is nearly completely absorbed and eliminated through the urine, and is thus exposed to many different proteins in the body. It binds at nanomolar levels to some carbonic anhydrases and this provokes the question of its inert properties. It is known that the plasma level slowly decreases after oral dosing, and CAVI binding could explain its unpleasant metallic aftertaste.

Structure-based drug discovery of carbonic anhydrase inhibitors

“…Other compounds possessing potent CAI activity and developed for other uses are celecoxib 13 and valdecoxib 14, originally described as cyclooxygenase 2 inhibitors 29,30 . Saccharin 15, widely used sweetener, is also a CAI, as recently reported by this and Klebe's groups 31 . Compounds 1-15 may be considered as first-/secondgeneration CAIs.…”

Determination of activities of human carbonic anhydrase II inhibitors from curcumin analogs

“…The initial structure of CA-II was obtained from the protein data bank (PDB), accession code 2Q38 [14]. Redocking LSA503 to the CA-II crystal structure was performed to derive docking parameters that will be used for the docking simulation with curcumin analogs.…”

Synthesis and in vivo diuretic activity of some new benzothiazole sulfonamides containing quinoxaline ring system

“…The schematical representation of the process may be shown by reactions 2 and 3. In reaction 3, the proton transfer regenerating the zinc-hydroxide species of the enzyme is a rate-limiting step in the catalysis (Figure 7) [15][16][17][18] . The rats were kept in metabolic cages for the measurement of the diuretic activity of the synthesized compounds.…”