title: Synthesis, acid-base behavior, and binding properties of 6-modified myo-inositol 1,4,5-tris(phosphate)s.
abstract: myo-Inositol 1,4,5-tris(phosphate) was modified at position 6. The analogues synthesized are reported in this publication are 6-deoxy-myo-inositol 1,4,5-tris(phosphate), 6-fluoro-6-deoxy-myo-inositol 1,4,5-tris(phosphate), epi-inositol 1, 4,5-tris(phosphate), and 6-amino-6-deoxy-myo-inositol 1,4, 5-tris(phosphate). These derivatives showed poor affinity for the Ins(1,4,5)P(3) receptors. The inframolecular acid-base behavior and the cooperative effects between the phosphate groups could help explain the loss of affinity of these 6-modified analogues.
authors.affiliation: Laboratoire de Pharmacochimie de la Communication Cellulaire UMR 7081 du CNRS, Faculté de Pharmacie, 74, route du Rhin, 67401 Illkirch, France.
authors.forename: S
authors.initials: S
authors.lastname: Ballereau
authors.forename: P
authors.initials: P
authors.lastname: Guédat
authors.forename: S N
authors.initials: SN
authors.lastname: Poirier
authors.forename: G
authors.initials: G
authors.lastname: Guillemette
authors.forename: B
authors.initials: B
authors.lastname: Spiess
authors.forename: G
authors.initials: G
authors.lastname: Schlewer
mesh_terms: D000302:Adrenal Cortex / Q000648:ultrastructure; D000818:Animals; D015220:Calcium Channels / Q000378:metabolism; D002417:Cattle; D006863:Hydrogen-Ion Concentration; D066298:In Vitro Techniques; D015544:Inositol 1,4,5-Trisphosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D053496:Inositol 1,4,5-Trisphosphate Receptors; D009682:Magnetic Resonance Spectroscopy; D008861:Microsomes / Q000378:metabolism; D011199:Potentiometry; D018160:Receptors, Cytoplasmic and Nuclear / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D015220:Calcium Channels; D053496:Inositol 1,4,5-Trisphosphate Receptors; D018160:Receptors, Cytoplasmic and Nuclear; D015544:Inositol 1,4,5-Trisphosphate