New Sugar‐Based Permeant Analogs of D‐Myo‐Inositol 1,4,5‐Trisphosphate Mimicking the Effect of Vasopressin: Synthesis and Biologic EvaluationFootnote*

* Dedicated to the memory of Jacques H. van Boom and his outstanding contribution to the field.

References and Notes

• Rasmussen , H. 1970 . Cell communication, calcium ion, and cyclic adenosine monophosphate . Science , 170 : 404 – 412 .
   PubMed Web of Science ®Google Scholar
• Putney , J. W.J. 1992 . Inositol Phosphate and Calcium Signalling New York : Raven Press .
   Google Scholar
• Chi , T. H. and Crabtree , G. R. 2000 . Signal transduction—Inositol phosphates in the nucleus . Science , 287 : 1937
   PubMed Web of Science ®Google Scholar
• Michell , R. H. 1975 . Inositol phospholipids and cell surface receptor function . Biochim. Biophys. Acta , 415 : 81 – 147 .
   PubMed Web of Science ®Google Scholar
• Streb , H. , Irvine , R. F. , Berridge , M. J. and Schulz , I. 1983 . Release of calcium(2+) from a nonmitochondrial intracellular store in pancreatic acinar cells by inositol‐1,4,5‐trisphosphate . Nature , 306 : 67 – 69 .
   PubMed Web of Science ®Google Scholar
• Berridge , M. J. and Irvine , R. F. 1984 . Inositol trisphosphate, a novel second messenger in cellular signal transduction . Nature , 312 : 315 – 321 .
   PubMed Web of Science ®Google Scholar
• Berridge , M. J. 1987 . Inositol trisphosphate and diacylglycerol two interacting second messengers . Annu. Rev. Biochem. , 56 : 159 – 193 .
   PubMed Web of Science ®Google Scholar
• Berridge , M. J. and Irvine , R. F. 1989 . Inositol phosphates and cell signalling . Nature , 341 : 197 – 203 .
   PubMed Web of Science ®Google Scholar
• Berridge , M. J. 1993 . Inositol trisphosphate and calcium signalling . Nature , 361 : 315 – 325 .
   PubMed Web of Science ®Google Scholar
• Taylor , C. W. and Richardson , A. 1991 . Structure and function of inositol trisphosphate receptors . Pharmac. Ther. , 51 : 97 – 137 .
   PubMed Web of Science ®Google Scholar
• Billington , D. C. 1989 . Recent developments in the synthesis of myo‐inositol phosphates . Chem. Soc. Rev. , 18 : 83 – 122 .
   Web of Science ®Google Scholar
• Potter , B. V.L. 1990 . Recent advances in the chemistry and biochemistry of inositol phosphates of biological interest . Nat. Prod. Reports , : 1 – 24 .
   PubMed Web of Science ®Google Scholar
• Potter , B. V.L. and Nahorski , S. R. 1993 . “ Synthetic inositol polyphosphates and analogues as molecular probes for neuronal second messengers receptors ” . In Drug Design for Neuroscience Edited by: Kozikowski , A. P. Vol. 14 , 383 – 416 . Raven Press .
   Google Scholar
• Potter , B. V.L. and Lampe , D. 1995 . Chemistry of inositol lipid mediated cellular signaling . Angew. Chem. Int. Ed. Engl. , 34 : 1933 – 1972 .
   Web of Science ®Google Scholar
• Poirot , E. , Bourdon , H. , Chrétien , F. , Chapleur , Y. , Berton , B. , Hilly , M. , Mauger , J.‐P. and Guillon , G. 1995 . Influence of the absolute configuration at C‐4 in the binding of D‐myo‐inositol 1,4,5‐trisphosphate analogues to IP3 receptors . Bioorg. Med. Chem. Lett. , 5 : 569 – 572 .
   Web of Science ®Google Scholar
• Wilcox , R. A. , Primrose , W. U. , Nahorski , S. and Chaliss , R. A.J. 1998 . New developments in the molecular pharmacology of the myo‐inositol 1,4,5‐trisphosphate receptor . TIPS , 19 : 467 – 475 .
   PubMed Web of Science ®Google Scholar
• Jenkins , D. J. , Riley , A. M. and Potter , B. V.L. 1998 . “ Carbohydrates as sources of chiral inositols polyphosphates and their mimics ” . In Carbohydrate Mimics Edited by: Chapleur , Y. 171 – 208 .
   Google Scholar
• Chrétien , F. , Moitessier , N. , Roussel , F. , Mauger , J. P. and Chapleur , Y. 2000 . Carbohydrate‐based mimics of D‐myo‐inositol 1,4,5‐ trisphosphate . Curr. Org. Chem. , 4 : 513 – 534 .
   Web of Science ®Google Scholar
• Moris , M.‐A. , Caron , A. Z. , Guillemette , G. and Schlewer , G. 2004 . Synthesis and binding properties of cyclopentane analogues of myo‐inositol 1,4,5‐tris(phosphate) . Bioorg. Med. Chem. , 12 : 3995 – 4001 .
   PubMedGoogle Scholar
• Moitessier , N. , Chrétien , F. , Chapleur , Y. and Humeau , C. 1995 . Synthesis and biological activities of inositol 1, 4, 5‐trisphosphate mimics related to xylopyranosides . Tetrahedron Lett. , 36 : 8023 – 8026 .
   Web of Science ®Google Scholar
• Moitessier , N. , Chrétien , F. and Chapleur , Y. 1997 . Asymmetric dihydroxylation of D‐xylose‐derived allyl ethers . Tetrahedron‐Asymmetry , 6 : 2889 – 2892 .
   Google Scholar
• Roussel , F. , Hilly , M. , Chrétien , F. , Mauger , J.‐P. and Chapleur , Y. 1999 . Synthesis of 2‐hydroxy ethyl 2‐deoxy‐a‐D‐threo pyranoside 3,4,2′‐trisphosphate, a mimic of the second messenger inositol 1,4,5‐trisphosphate . J. Carbohydr. Chem. , 18 : 697 – 707 .
   Web of Science ®Google Scholar
• Rosenberg , H. J. , Riley , A. M. , Marwood , R. D. , Correa , V. , Taylor , C. W. and Potter , B. V.L. 2001 . Xylopyranoside‐based agonists of D‐myo‐inositol 1,4,5‐trisphosphate receptors: synthesis and effect of stereochemistry on biological activity . Carbohydr. Res. , 332 : 53 – 66 .
   PubMed Web of Science ®Google Scholar
• Roussel , F. , Moitessier , N. , Hilly , M. , Chrétien , F. , Mauger , J.‐P. and Chapleur , Y. 2002 . D‐myo‐inositol‐1,4,5‐trisphosphate and adenophostin mimics: importance of the spacial orientation of a phosphate groupe on the biological activity . Bioorg. Med. Chem. , 10 : 759 – 768 .
   PubMed Web of Science ®Google Scholar
• Takahashi , S. , Kinoshita , T. and Takahashi , M. 1994 . Adenophostins A and B: potent agonists of inositol‐1,4,5‐trisphosphate receptor produced by Penicillium brevicompactum. Structure elucidation. . J. Antibiotics , 47 : 95 – 100 .
   PubMed Web of Science ®Google Scholar
• Takahashi , M. , Tanzawa , K. and Takahashi , S. 1994 . Adenophostins, newly discovered metabolites of Penicillium brevicompactum, act as potent agonists of inositol 1,4,5‐trisphosphate receptor . J. Biol. Chem. , 289 : 369 – 372 .
   Google Scholar
• Hotoda , H. , Takahashi , M. , Tanzawa , K. , Takahashi , S. and Kaneko , M. 1995 . IP3 receptor‐ligand. 1 . Synthesis of adenophostin A. Tetrahedron Lett. , 36 : 5037 – 5040 .
   Web of Science ®Google Scholar
• van Straten , N. C.R. , van der Marel , G. A. and van Boom , J. H. 1996 . An expeditious route to the synthesis of adenophostin A . Tetrahedron Lett. , 37 : 3599 – 3602 .
   Web of Science ®Google Scholar
• van Straten , N. C.R. , van der Marel , G. A. and van Boom , J. H. 1997 . An expeditious route to the synthesis of adenophostin A . Tetrahedron , 53 : 6509 – 6522 .
   Web of Science ®Google Scholar
• Marwood , R. D. , Riley , A. M. , Jenkins , D. J. and Potter , B. V.L. 2000 . Synthesis of adenophostin A and congeners modified at glucose . J. Chem. Soc., Perkin Trans. 1 , : 1935 – 1947 .
   Google Scholar
• Marwood , R. D. , Correa , V. , Taylor , C. W. and Potter , B. V.L. 2000 . Synthesis of adenophostin A . Tetrahedron‐Asymmetry , 11 : 397 – 403 .
   Google Scholar
• Jenkins , D. J. and Potter , B. V.L. 1995 . (2‐hydroxyethyl)‐alpha‐D‐Glucopyranoside‐2′‐3,4‐trisphosphates: synthesis of a second messenger mimic related to adenophostin A . J. Chem. Soc., Chem. Commun. , : 1169
   Google Scholar
• Jenkins , D. J. and Potter , B. V.L. 1996 . A Ca2+‐mobilising carbohydrate‐based polyphosphate: synthesis of 2‐hydroxyethyl alpha‐D‐glucopyranoside 2′,3,4‐trisphosphate . Carbohydr. Res. , 287 : 169 – 182 .
   PubMed Web of Science ®Google Scholar
• Jenkins , D. J. , Marwood , R. D. and Potter , B. V.L. 1997 . A disaccharide polyphosphate mimic of 1D‐myo‐inositol 1,4,5‐ trisphosphate . Chem. Commun. , : 449 – 450 .
   Web of Science ®Google Scholar
• van Straten , N. C.R. , van der Marel , G. A. and van Boom , J. H. 1997 . Synthesis of 2′,3″,4″‐trisphosphate‐containing analogs of adenophostin A . Tetrahedron , 53 : 6523 – 6538 .
   Web of Science ®Google Scholar
• van Straten , N. C.R. , Kriek , N. M.A.J. , Cziria , Z. A.C. , van der Marel , G. A. and van Boom , J. H. 1997 . Synthesis of 3″,4″‐bisphosphate‐containing analogs of adenophostin A . Tetrahedron , 53 : 6539 – 6554 .
   Web of Science ®Google Scholar
• de Kort , M. , Valentijn , A. R.P.M. , van der Marel , G. A. and van Boom , J. H. 1997 . Synthesis of clustered disaccharide polyphosphate analogues of adenophostin A . Tetrahedron Lett. , 38 : 7629 – 7632 .
   Web of Science ®Google Scholar
• Shuto , S. , Tatani , K. , Ueno , Y. and Matsuda , A. 1998 . Synthesis of adenophostin analogues lacking the adenine moiety as novel potent IP3 receptor ligands: some structural requirements for the significant activity of adenophostin A . J. Org. Chem. , 63 : 8815 – 8824 .
   Web of Science ®Google Scholar
• Tatani , K. , Shuto , S. , Ueno , Y. and Matsuda , A. 1998 . Synthesis of 1‐O‐[(3S,4R)‐3‐hydroxytetrahydrofuran‐4‐yl]‐ alpha‐D‐gluco‐pyranoside 3,4,3′‐trisphosphate as a novel potent IP3 receptor ligand . Tetrahedron Lett. , 39 : 5065 – 5068 .
   Web of Science ®Google Scholar
• Riley , A. M. and Potter , B. V.L. 1999 . Bicyclic analogues of inositol 1,4,5‐trisphosphate based upon adenophostin A . Tetrahedron Lett. , 40 : 2213 – 2216 .
   Web of Science ®Google Scholar
• Marwood , R. D. , Riley , A. M. , Correa , V. , Taylor , C. W. and Potter , B. V. 1999 . Simplification of adenophostin A defines a minimal structure for potent glucopyranoside‐based mimics of D‐myo‐inositol 1,4,5‐trisphosphate . Bioorg. Med. Chem. Lett , 9 : 453 – 458 .
   PubMed Web of Science ®Google Scholar
• Abe , H. , Shuto , S. and Matsuda , A. 2000 . Synthesis of the C‐glycosidic analog of adenophostin A, a potent IP3 receptor agonist, using a temporary silicon‐ tethered radical coupling reaction as the key step . Tetrahedron Lett. , 41 : 2391 – 2394 .
   Web of Science ®Google Scholar
• Abe , H. , Shuto , S. and Matsuda , A. 2000 . Synthesis of the C‐glycosidic analogue of adenophostin A and its uracil congener as potential IP3 receptor ligands. Stereoselective construction of the C‐glycosidic structure by a temporary silicon‐tethered radical coupling reaction . J. Org. Chem. , 65 : 4315 – 4325 .
   PubMed Web of Science ®Google Scholar
• Shuto , S. , Yahiro , Y. , Ichikawa , S. and Matsuda , A. 2000 . Synthesis of 3,7‐anhydro‐D‐glycero‐D‐ido‐octitol 1,5,6‐ trisphosphate as an IP3 receptor ligand using a radical cyclization reaction with a vinylsilyl tether as the key step. Conformational restriction strategy using steric repulsion between adjacent bulky protecting groups on a pyranose ring . J. Org. Chem. , 65 : 5547 – 5557 .
   PubMed Web of Science ®Google Scholar
• de Kort , M. , Regenbogen , A. D. , Overkleeft , H. S. , Challiss , R. A.J. , Iwata , Y. , Miyamoto , S. , van der Marel , G. A. and van Boom , J. H. 2000 . Synthesis and biological evaluation of cyclophostin: a 5′,6″‐tethered analog of adenophostin A . Tetrahedron , 56 : 5915 – 5928 .
   Web of Science ®Google Scholar
• de Kort , M. , Regenbogen , A. D. , Valentijn , A. R.P.M. , Challiss , R. A.J. , Iwata , Y. , Miyamoto , S. , van der Marcel , G. A. and van Boom , J. H. 2000 . Spirophostins: conformationally restricted analogues of adenophostin A . Chem. Eur. J. , 6 : 2696 – 2704 .
   PubMed Web of Science ®Google Scholar
• de Kort , M. , Luijendijk , J. , van der Marel , G. A. and van Boom , J. H. 2000 . Synthesis of photoaffinity derivatives of adenophostin A . Eur. J. Org. Chem. , : 3085 – 3092 .
   Google Scholar
• Shuto , S. , Horne , G. , Marwood , R. D. and Potter , B. V.L. 2001 . Total synthesis of nucleobase‐modified adenophostin A mimics . Chem. Eur. J. , 7 : 4937 – 4946 .
   PubMed Web of Science ®Google Scholar
• Hirota , J. , Michikawa , T. , Miayawaki , A. , Takahashi , M. , Tanzawa , K. , Okura , I. , Furuichi , T. and Mikoshiba , K. 1995 . Adenophostin‐medicated quantal Ca2+ release in the purified and reconstituted inositol 1,4,5‐trisphosphate receptor type 1 . FEBS Lett. , 368 : 248 – 252 .
   PubMed Web of Science ®Google Scholar
• Wilcox , R. A. , Erneux , C. , Primrose , W. U. , Gigg , R. and Nahorski , S. 1995 . 2‐hydroxyethyl‐a‐D‐glucopyranoside‐2,3′,4′‐trisphosphate, a novel metabolically resistant adenophostin A and myo‐inositol‐1,4,5‐trisphosphate analogue, potently interacts with the myo‐inositol‐1,4,5‐trisphosphate receptor . Mol. Pharmacol. , 47 : 1204 – 1211 .
   PubMed Web of Science ®Google Scholar
• Murphy , C. T. , Riley , A. M. , Lindley , C. J. , Jenkins , D. J. , Westwich , J. and Potter , B. V.L. 1997 . Structural analogues of D‐myo‐inositol‐1,4,5‐trisphosphate and adenophostin A/Recognition by cerebellar and platelet inositol‐1,4,5‐trisphosphate receptors . Mol. Pharmacol. , 52 : 741 – 748 .
   PubMed Web of Science ®Google Scholar
• Beecroft , M. D. , Marchant , J. S. , Riley , A. M. , van Straten , N. C.R. , van der Marel , G. A. , van Boom , J. H. , Potter , B. V.L. and Taylor , C. W. 1999 . Acyclophostin/A ribose modified analog of adenophostin A with high affinity for inositol 1,4,5‐trisphosphate receptors and pH‐dependent efficacy . Mol. Pharmacol. , 55 : 109 – 117 .
   PubMed Web of Science ®Google Scholar
• De Lisle , S. , Marksberry , E. W. , Bonnett , C. , Jenkins , D. J. , Potter , B. V.L. , Takahashi , M. and Tanzawa , K. 1997 . Adenophostin A can stimulate Ca2+ influx without depleting the inositol 1,4,5‐trisphoshate sensitive Ca2+ stores in the Xenopu oocyte . J. Biol. Chem. , 272 : 9956 – 9961 .
   PubMed Web of Science ®Google Scholar
• Marchant , J. S. , Beecroft , M. D. , Riley , A. M. , Jenkins , D. J. , Marwood , R. D. , Taylor , C. W. and Potter , B. V.L. 1997 . Disaccharide polyphosphates based upon adenophostin A activate hepatic D‐myo‐inositol 1,′,(‐trisphosphate receptors . Biochemistry , 36 : 12780 – 12790 .
   PubMed Web of Science ®Google Scholar
• Hotoda , H. , Murayama , K. , Miyamoto , S. , Iwata , Y. , Takahashi , M. , Kawase , Y. , Tanzawa , K. and Kaneko , M. 1999 . Molecular recognition of adenophostin, a very potent Ca2+ inducer at the D‐myo‐inositol 1,4,5‐trisphosphate receptor . Biochemistry , 38 : 9234 – 9241 .
   PubMed Web of Science ®Google Scholar
• Sato , Y. , Miyazaki , S. , Shikano , T. , Mitsuhashi , N. , Takeuchi , H. , Mikoshiba , K. and Kuwabara , Y. 1998 . Adenophostin a potent agonist of the inositol 1,4,5‐trisphosphate receptor is useful for fertilization of mouse oocytes injected with round spermatids leading to normal off spring . Biol. Reprod. , 58 : 867 – 873 .
   PubMed Web of Science ®Google Scholar
• Correa , V. , Riley , A. M. , Shuto , S. , Horne , G. , Nerou , E. P. , Marwood , R. D. , Potter , B. V.L. and Taylor , C. W. 2001 . Structural determinants of adenophostin a activity at inositol trisphosphate receptors . Mol. Pharmacol. , 59 : 1206 – 1215 .
   PubMed Web of Science ®Google Scholar
• Roemer , S. , Rudolf , M. T. , Stadler , C. and Schultz , C. 1995 . Synthesis of D‐myo‐inositol 3,4,5,6‐ and 1,4,5,6‐tetrakisphosphate analogs and their membrane‐permeant derivatives . J. Chem. Soc. Chem. Commun. , : 411 – 412 .
   Google Scholar
• Roemer , S. , Stadler , C. , Rudolf , M. T. , Jastorff , B. and Schultz , C. 1996 . Membrane‐permeant analogues of the putative second messenger myo‐inositol 3,4,5,6‐tetrakisphosphate . J. Chem. Soc., Perkin Trans. 1 , : 1683 – 1694 .
   Google Scholar
• Li , W. H. , Schultz , C. , Llopis , J. and Tsien , R. Y. 1997 . Membrane‐permeant esters of inositol polyphosphates, chemical syntheses and biological applications . Tetrahedron , 53 : 12017 – 12040 .
   Web of Science ®Google Scholar
• Li , W. H. , Llopis , J. , Whitney , M. , Zlokarnik , G. and Tsien , R. Y. 1998 . Cell‐permeant caged InsP(3) ester shows that Ca2+ spike frequency can optimize gene expression . Nature , 392 : 936 – 941 .
   PubMed Web of Science ®Google Scholar
• Rudolf , M. T. , Traynor‐Kaplan , A. E. and Schultz , C. 1998 . A membrane‐permeant, bioactivatable derivative of Ins(1,3,4)P3 and its effect on Cl(‐)‐secretion from T84 cells . Bioorg. Med. Chem. Lett , 8 : 1857 – 1860 .
   PubMed Web of Science ®Google Scholar
• Dubreuil , D. , Cleophax , J. , Viera de Almeida , M. , Verre Sebrie , C. , Pipelier , M. , Vass , G. and Gero , S. D. 1999 . Stereoselective synthesis of myo‐inositol‐1,3,4,5‐ tetrakisphosphate analogues from 6‐deoxy D‐inositol precursors . Tetrahedron , 55 : 7573 – 7582 .
   Web of Science ®Google Scholar
• de Almeida , M. V. , Cleophax , J. , Gateau‐Olesker , A. , Prestat , G. , Dubreuil , D. and Gero , S. D. 1999 . Synthesis of deoxy phosphatidylinositol analogues and phosphonate isosters of Ins(1,4,5)P‐3 . Tetrahedron , 55 : 12997 – 13010 .
   Web of Science ®Google Scholar
• de Almeida , M. V. , Dubreuil , D. , Cleophax , J. , VerreSebrie , C. , Pipelier , M. , Prestat , G. , Vass , G. and Gero , S. D. 1999 . Stereoselective synthesis of inositol mono, bis and trisphosphate analogues from 6‐deoxy‐D‐inositol precursors . Tetrahedron , 55 : 7251 – 7270 .
   Web of Science ®Google Scholar
• Bannwarth , W. and Trzeciak , A. 1987 . A simple and effective chemical phosphorylation procedure for biomolecules . Helv. Chim. Acta , 70 : 175 – 186 .
   Web of Science ®Google Scholar
• Marugg , J. E. , Tromp , M. , Kuyl‐Yeheskiely , E. , van der Marel , G. A. and van Boom , J. H. 1986 . A convenient and general approach to the synthesis of properly protected d‐nucleoside‐3′‐hydrogenphosphonates via phosphite intermediates . Tetrahedron Lett. , 27 : 2661 – 2664 .
   Web of Science ®Google Scholar
• Knerr , L. , Pannecouke , X. , Schmitt , G. and Luu , B. 1996 . Preferential phosphorylation at the primary alcohol of non‐protected thymidine or carbohydrates . Tetrahedron Lett. , 37 : 5123 – 5126 .
   Web of Science ®Google Scholar
• Garegg , P. J. , Lindh , I. , Regberg , T. , Stawinski , J. , Stroemberg , R. and Henrichson , C. 1986 . Nucleoside H‐phosphonates. III. Chemical synthesis of oligodeoxyribonucleotides by the hydrogenphosphonate approach. . Tetrahedron Lett. , 27 : 4051 – 4054 .
   Web of Science ®Google Scholar
• Froehler , B. C. and Matteucci , M. D. 1986 . Nucleoside h‐phosphonates: valuable intermediates in the synthesis of deoxyoligonucleotides . Tetrahedron Lett. , 27 : 469 – 472 .
   Web of Science ®Google Scholar
• Garegg , P. J. , Regberg , T. , Stawinski , J. and Stroemberg , R. 1987 . Studies on the synthesis of oligonucleotides via the hydrogen phosphonate approach . Nucleosides & Nucleotides , 6 : 283 – 286 .
   Google Scholar
• Garegg , P. J. , Regberg , T. , Stawinski , J. and Stroemberg , R. 1987 . Studies on the oxidation of nucleoside hydrogen phosphonates . Nucleosides & Nucleotides , 6 : 429 – 32 .
   Web of Science ®Google Scholar
• Schultz , C. 2003 . Prodrugs of biologically active phosphate esters . Bioorg. Med. Chem. , 11 : 885 – 898 .
   PubMed Web of Science ®Google Scholar
• Jansen , A. B.A. and Russell , T. J. 1965 . Novel penicillin derivatives . Chem. Soc. , : 2127 – 2132 .
   PubMed Web of Science ®Google Scholar
• Ferres , H. 1980 . Pro‐drugs of b‐lactam antibiotics . Chem. Ind. , : 435 – 440 .
   Web of Science ®Google Scholar
• Schultz , C. , Vajanaphanich , M. , Harootunian , A. T. , Sammak , P. J. , Barrett , K. E. and Tsien , R. Y. 1993 . Acetoxymethyl esters of phosphates, enhancement of the permeability and potency of cAMP . J. Biol. Chem. , 268 : 6316 – 6122 .
   PubMed Web of Science ®Google Scholar
• Vajanaphanich , M. , Schultz , C. , Rudolf , M. T. , Wasserman , M. , Enyedi , P. , Craxton , A. , Shears , S. B. , Tsien , R. Y. , Barrett , K. E. and Traynor‐Kaplan , A. 1994 . Long‐term uncoupling of chloride secretion from intracellular calcium levels by Ins(3,4,5,6)P4 . Nature , 371 : 711 – 714 .
   PubMed Web of Science ®Google Scholar
• Bodor , N. , Kaminski , J. J. and Selk , S. 1980 . Soft drugs. 1. Labile quaternary ammonium salts as soft antimicrobials . J. Med. Chem. , 23 : 469 – 474 .
   PubMed Web of Science ®Google Scholar
• Bedford , C. D. , Harris , R. N.I. , Howd , R. A. , Goff , D. A. , Koolpe , G. A. , Petesch , M. , Miller , A. , Nolen , H. W.I. , Musallam , H. A. , Pick , R. O. , Jones , D. E. , Koplovitz , I. and Sultan , W. E. 1989 . Quaternary salts of 2‐[(hydroxyimino)methyl]imidazole. 2. Preparation and in vitro and in vivo evaluaton of 1‐(alkoxymethyl)‐2‐[(hydroxyimino)methyl]‐3‐methylimidazolium halides for reactivation of organophosphorus‐inhibited acetylcholinesteases . J. Med. Chem. , 32 : 493 – 503 .
   PubMed Web of Science ®Google Scholar
• Grynkiewicz , G. and Tsien , R. Y. 1987 . Preparation of acyloxymethyl halides from acylals . Pol. J. Chem. , 61 : 443 – 447 .
   Google Scholar
• Prestwich , G. D. , Marecek , J. F. , Mourey , R. J. , Theibert , A. B. , Ferris , C. D. , Danoff , S. K. and Snyder , S. H. 1991 . Tethered IP3. Synthesis and biochemical applications of the 1‐O‐(3‐aminopropyl) ester of inositol 1,4,5‐trisphosphate . J. Am. Chem. Soc. , 113 : 1822 – 1825 .
   Web of Science ®Google Scholar
• Prestwich , G. D. 1996 . Touching all the bases: synthesis of inositol polyphosphate and phosphoinositide affinity probes from glucose . Acc. Chem. Res. , 29 : 503 – 513 .
   Web of Science ®Google Scholar
• Mourey , R. J. , Estevez , V. A. , Marecek , J. F. , Barrow , R. K. , Prestwich , G. D. and Synder , S. H. 1993 . Inositol 1,4,5‐trisphosphate receptors: labelling the inositol 1,4,5‐trisphosphate binding site with photoaffinity ligands . Biochemistry , 32 : 1719 – 1726 .
   PubMed Web of Science ®Google Scholar
• Dorman , G. and Prestwich , G. D. 1994 . Benzophenone photophores in biochemistry . Biochemistry , 33 : 5661 – 5673 .
   PubMed Web of Science ®Google Scholar
• Jenkins , D. J. and Potter , B. V.L. 1998 . Total synthesis, from D‐xylose, of chiral, ring‐contracted 1D‐myo‐inositol 1,4,5‐trisphosphate and 1,3,4,5‐ tetrakisphosphate analogues with C‐2 excised . J. Chem. Soc. Perkin Trans. 1 , : 41 – 49 .
   Google Scholar
• Ram , S. and Spicer , L. D. 1988 . Reduction of aldehydes and ketones to methylen derivatives using ammonium formate as a catalytic hydrogen transfer agent . Tetrahedron Lett. , 29 : 3741 – 3744 .
   Web of Science ®Google Scholar
• Inoue , T. , Kikuchi , K. , Hirose , K. , Iino , M. and Nagano , T. 1999 . Synthesis and evaluation of 1‐position‐modified inositol 1,4,5‐ trisphosphate analogs . Bioorg. Med. Chem. Lett , 9 : 1697 – 1702 .
   PubMedGoogle Scholar
• Williamson , J. R. , Cooper , R. H. , Joseph , S. K. and Thomas , A. P. 1985 . Inositol trisphosphate and diacylglycerol as intracellular second messengers in liver . Am. J. Physiol. , 248 : C203 – C216 .
   PubMed Web of Science ®Google Scholar
• Putney , J. W.J. , Broad , L. M. , Braun , F. J. , Lievremont , J. P. and Bird , G. S. 2001 . Mechanisms of capacitative calcium entry . J. Cell Sci. , 114 : 2223 – 2229 .
   PubMed Web of Science ®Google Scholar
• Seglen , P. O. 1976 . Preparation of isolated rat liver cells . Meth. Cell. Biol , 13 : 29 – 83 .
   PubMedGoogle Scholar
• Tordjmann , T. , Berthon , B. , Claret , M. and Combettes , L. 1997 . Coordinated intercellular calcium waves induced by noradrenaline in rat hepatocytes: dual control by gap junction permeability and agonist . EMBO J. , 16 : 5398 – 5407 .
   PubMed Web of Science ®Google Scholar