Cyclic taurine analogs. Synthesis and effects on ATP-dependent Ca2+ uptake in rat retina.
Syntheses of (+/-)trans- and (+/-)cis-2-aminocyclohexane sulfonic acid (TAHS and CAHS) and (+/-)trans-2-aminocyclopentane sulfonic acid (TAPS) were achieved. In solution, the preferred conformations of TAHS and CAHS have been determined by high field NMR to be diequatorial and equatorial (sulfonic acid moiety)-axial (amino moiety) respectively. When these agents were evaluated as cyclic analogs of taurine in rat retina, TAHS and TAPS inhibited ATP-dependent calcium uptake in the micromolar range, whereas CAHS stimulated calcium uptake in the millimolar range in a manner similar to taurine. TAHS and TAPS are the most potent inhibitors of ATP-dependent calcium uptake in the rat retinal preparation yet reported.
D000255:Adenosine Triphosphate / Q000494:pharmacology*; D000818:Animals; D002118:Calcium / Q000378:metabolism*; D003514:Cyclohexylamines / Q000138:chemical synthesis / Q000494:pharmacology; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D051381:Rats; D011919:Rats, Inbred Strains; D012160:Retina / Q000187:drug effects / Q000378:metabolism*; D013654:Taurine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
D003514:Cyclohexylamines; D003517:Cyclopentanes; C052782:2-aminocyclopentanesulfonic acid; C052781:2-aminocyclohexanesulfonic acid; D013654:Taurine; D000255:Adenosine Triphosphate; D002118:Calcium