Dimers of D-myo-Inositol 1,4,5-Trisphosphate: Design, Synthesis, and Interaction with Ins(1,4,5)P3 Receptors

Bioconjugate Chemistry

Volumn 15, Issue 2, 2004, Pages 278-289

  Riley, Andrew M ^a   Laude, Alex J ^b   Taylor, Colin W ^b   Potter, Barry V L ^a  

^a University of Bath   (United Kingdom)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMATOGRAPHIC ANALYSIS; DIMERS; ION CHROMATOGRAPHY; ION EXCHANGE; POLYETHYLENE GLYCOLS; SUGARS; SYNTHESIS (CHEMICAL); TETHERLINES;

B-Y IONS; CA 2+; DEPROTECTION; DESIGN SYNTHESIS; HEPATOCYTES; INTRACELLULAR SIGNALING MOLECULES; ION EXCHANGE CHROMATOGRAPHY; MYO-INOSITOL; TETRAMERIC; WATERSOLUBLE;

POLYOLS;

2 O (2 AMINOETHYL)INOSITOL 1,4,5 TRIPHOSPHATE; ADENOPHOSTIN A; AMIDE; BENZYL DERIVATIVE; CALCIUM ION; CARBAMIC ACID; DIMER; INOSITOL 1,4,5 TRISPHOSPHATE; INOSITOL 1,4,5 TRISPHOSPHATE DERIVATIVE; INOSITOL 1,4,5 TRISPHOSPHATE RECEPTOR; LIGAND; MACROGOL; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BINDING SITE; CALCIUM TRANSPORT; CELL MEMBRANE; CEREBELLUM; CONJUGATION; CROSS LINKING; CRYSTAL STRUCTURE; DEPROTECTION REACTION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; EQUILIBRIUM CONSTANT; ION EXCHANGE CHROMATOGRAPHY; LIVER CELL; MOLECULAR SIZE; NONHUMAN; RAT; SIGNAL TRANSDUCTION; SOLUBILITY;

ANIMALIA;

EID: 1642269083     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc034214s     Document Type: Article

References (44)

1. Berridge, M. J., Lipp, P., and Bootman, M. D. (2000) The versatility and universality of calcium signaling. Nature Rev. Mol. Cell Biol. 1, 11-21.
2. Takahashi, M., Tanzawa, K., and Takahashi, S. (1994) Adenophostins, newly discovered metabolites of Penicillium brevicompactum, act as potent agonists of the inositol 1,4,5-trisphosphate receptor. J. Biol. Chem. 269, 369-372.
3. Morris, S. A., Nerou, E. P., Riley, A. M., Potter, B. V. L., and Taylor, C. W. (2002) Determinants of adenophostin A binding to inositol trisphosphate receptors. Biochem. J. 367, 113-120.
4. 2+ inducer, at the D-myo-inositol 1,4, 5-trisphosphate receptor. Biochemistry 38, 9234-9241.
5. 3 receptor interaction. J. Med. Chem. 46, 4860-4871.
6. Mammen, M., Choi, S.-K., and Whitesides, G. M. (1998) Polyvalent interactions in biological systems: implications for design and use of multivalent ligands and inhibitors. Angew. Chem., Int. Ed. Engl. 37, 2754-2794.
7. Portoghese, P. S. (2001) From models to molecules: opioid receptor dimers, bivalent ligands, and selective opioid receptor probes. J. Med. Chem. 44, 2259-2269.
8. Gordon, E. J., Gestwicki, J. E., Strong, L. E., and Kiessling, L. L. (2000) Synthesis of end-labeled multivalent ligands for exploring cell-surface-receptor-ligand interactions. Chem. Biol. 7, 9-16.
9. Fan, E., Zhang, Z., Minke, W. E., Hou, Z., Verlinde, C. L. M. J., and Hol, W. G. J. (2000) High-affinity pentavalent ligands of Escherichia coli heat-labile enterotoxin by modular structure-based design. J. Am. Chem. Soc. 122, 2663-2664.
10. Loidl, G., Groll, M., Musiol, H.-J., Huber, R., and Moroder, L. (1999) Bivalency as a principle for proteasome inhibition. Proc. Natl. Acad. Sci. U.S.A. 96, 5418-5422.
11. Schaschke, N., Matschiner, G., Zettl, F., Marquardt, U., Bergner, A., Bode, W., Sommerhoff, C. P., and Moroder, L. (2001) Bivalent inhibition of human β-tryptase. Chem. Biol. 8, 313-327.
12. Lyon, R. P., Hill, J. J., and Atkins, W. M. (2003) Novel class of bivalent glutathione S-transferase inhibitors. Biochemistry 42, 10418-10428.
13. de Kort, M., Correa, V., Valentijn, A. R. P. M., van der Marel, G. A., Potter, B. V. L., Taylor, C. W., and van Boom, J. H. (2000) Synthesis of potent agonists of the D-myo-inositol 1, 4, 5-trisphosphate receptor based on clustered disaccharide polyphosphate analogues of adenophostin A. J. Med. Chem. 43, 3295-3303.
14. Chadwick, C. C., Saito, A., and Fleischer, S. (1990) Isolation and characterization of the inositol trisphosphate receptor from smooth muscle. Proc. Natl. Acad. Sci. U.S.A. 87, 2132-2136.
15. Katayama, E., Funahashi, H., Michikawa, T., Shiraishi, T., Ikemoto, T., Iino, M., Hirosawa, K., and Mikoshiba, K. (1996) Native structure and arrangement of inositol-1,4,5-trisphosphate receptor molecules in bovine cerebellar Purkinje cells as studied by quick-freeze deep-etch electron microscopy. EMBO J. 15, 4844-4851.
16. Hamada, K., Miyata, T., Mayanagi, K., Hirota, J., and Mikoshiba, K. (2002) Two-state conformational changes in inositol 1,4,5-trisphosphate receptor regulated by calcium. J. Biol. Chem. 277, 21115-21118.
17. da Fonseca, P. C. A., Morris, S. A., Nerou, E. P., Taylor, C. W., and Morris, E. P. (2003) Domain organisation of the type 1 inositol 1,4,5-trisphosphate receptor as revealed by single-particle analysis. Proc. Natl. Acad. Sci. U.S.A. 100, 3936-3941.
18. Serysheva, I. I., Bare, D. J., Ludtke, S. J., Kettlun, C. S., Chiu, W., and Mignery, G. A. (2003) Structure of the type 1 inositol 1,4,5-trisphosphate receptor revealed by electron cryomicroscopy. J. Biol. Chem. 278, 21319-21322.
19. Kramer, R. H., and Karpen, J. W. (1998) Spanning binding sites on allosteric proteins with polymer-linked ligand dimers. Nature 395, 710-713.
20. Riley, A. M., and Potter, B. V. L. (2000) Poly(ethylene glycol)-linked dimers of D-myo-inositol 1,4,5-trisphosphate. Chem. Commun. 983-984.
21. Riley, A. M., Morris, S. A., Nerou, E. P., Correa, V., Potter, B. V. L., and Taylor, C. W. (2002) Interactions of inositol 1,4,5-trisphosphate (IP3) receptors with synthetic poly(ethylene glycol)-linked dimers of IP3 suggest close spacing of the IP3-binding sites. J. Biol. Chem. 277, 40290-40295.
22. 2+-mobilizing inhibitors of D-myo-inositol 1,4,5-trisphosphate 5-phosphatase. J. Med. Chem. 37, 907-912.
23. Ames, B. N., and Dubin, D. T. (1960) The role of polyamines in the neutralization of bacteriophage deoxyribonucleic acid. J. Biol. Chem. 235, 769-775.
24. Jones, G., Willett, P., Glen, R. C., Leach, A. R., and Taylor, R. (1997) Development and validation of a genetic algorithm for flexible docking. J. Mol. Biol. 267, 727-748.
25. Bosanac, I., Alattia, J.-R., Mal, T. K., Chan, J., Talarico, S., Tong, F. K., Tong, K. I., Yoshikawa, F., Furuichi, T., Iwai, M., Michikawa, T., Mikoshiba, K., and Ikura, M. (2002) Structure of the inositol 1,4,5-trisphosphate receptor binding core in complex with its ligand. Nature 420, 696-700.
26. Riley, A. M., Correa, V., Mahon, M. F., Taylor, C. W., and Potter, B. V. L. (2001) Bicyclic analogues of D-myo-inositol 1,4,5-trisphosphate related to adenophostin A: synthesis and biological activity. J. Med. Chem. 44, 2108-2117.
27. Wittmann, V., Takayama, S., Gong, K. W., Weitz-Schmidt, G., and Wong, C.-H. (1998) Ligand recognition by E- and P-selectin: chemoenzymatic synthesis and inhibitory activity of bivalent sialyl Lewis x derivatives and sialyl Lewis x carboxylic acids. J. Org. Chem. 63, 5137-5143.
28. Yamashita, K., Janout, V., Bernard, E. M., Armstrong, D., and Regen, S. L. (1995) Micelle/monomer control over the membrane-disrupting properties of an amphiphilic antibiotic. J. Am. Chem. Soc. 117, 6249-6253.
29. Hirata, M., Yanaga, F., Koga, T., Ogasawara, T., Watanabe, Y., and Ozaki, S. (1990) Stereospecific recognition of inositol 1,4,5-trisphosphate analogues by the phosphatase, kinase, and binding proteins. J. Biol. Chem. 265, 8404-8407.
30. Potter, B. V. L., and Lampe, D. (1995) Chemistry of inositol lipid-mediated cellular signaling. Angew. Chem., Int. Ed. Engl. 34, 1933-1972.
31. Malet, C., and Hindsgaul, O. (1996) Versatile functionalization of carbohydrate hydroxyl groups through their O-cyanomethyl ethers. J. Org. Chem. 61, 4649-4654.
32. Xu, D., Prasad, K., Repic, O., and Blacklock, T. J. (1995) Ethyl trifluoroacetate - a powerful reagent for differentiating amino-groups. Tetrahedron Lett. 36, 7357-7360.
33. Baker, R., and Castro, J. L. (1990) Total synthesis of (+)-macbecin-I. J. Chem. Soc., Perkin Trans. 1 47-65.
34. Zalipsky, S. (1995) Functionalized poly(ethylene glycol) for preparation of biologically relevant conjugates. Bioconjugate Chem. 6, 150-165.
35. Miron, T., and Wilchek, M. (1993) A simplified method for the preparation of succinimidyl carbonate poly(ethylene glycol) for coupling to proteins. Bioconjugate Chem. 4, 568-569.
36. Morpurgo, M., Bayer, E. A., and Wilchek, M. (1999) N-hydroxysuccinimide carbonates and carbamates are useful reactive reagents for coupling ligands to lysines on proteins. J. Biochem. Biophys. Methods 38, 17-28.
37. Izdebski, J., and Pawlak, D. (1989) A new convenient method for the synthesis of symmetrical and unsymmetrical N,N′-disubstituted ureas. Synthesis 423-425.
38. Knoll, D., and Hermans, J. (1983) Polymer-protein interactions. Comparison of experiment and excluded volume theory. J. Biol. Chem. 258, 5710-5715.
39. Kiessling, L. L., Gestwicki, J. E., and Strong, L. E. (2000) Synthetic multivalent ligands in the exploration of cell-surface interactions. Curr. Opin. Chem. Biol. 4, 696-703.
40. Gestwicki, J. E., Cairo, C. W., Strong, L. E., Oetjen, K. A., and Kiessling, L. L. (2002) Influencing receptor-ligand binding mechanisms with multivalent ligand architecture. J. Am. Chem. Soc. 124, 14922-14933.
41. Pohl, N. L., and Kiessling, L. L. (1999) Scope of multivalent ligand function: lactose-bearing neoglycopolymers by ring-opening metathesis polymerization. Synthesis, 1515-1519.
42. Lemmon, M. A., and Ferguson, K. M. (2000) Signal-dependent membrane targeting by pleckstrin homology (PH) domains. Biochem. J. 350, 1-18.
43. Stenmark, H., Aasland, R., and Driscoll, P. C. (2002) The phosphatidylinositol 3-phosphate-binding FYVE finger. FEBS Lett. 513, 77-84.
44. Hamada, K., Terauchi, A., and Mikoshiba, K. (2003) Three-dimensional rearrangements within inositol 1,4,5-trisphosphate receptors by calcium. J. Biol. Chem. 278, 52881-52889.