Adenophostins: High-affinity agonists of IP 3 receptors

Current Topics in Membranes

Volumn 66, Issue C, 2010, Pages 209-233

  Rossi, Ana M ^a   Riley, Andrew M ^b   Potter, Barry V L ^b   Taylor, Colin W ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b University of Bath   (United Kingdom)

Author keywords

Adenophostin; Ca channel; IP 3; IP 3 receptor; Structure activity relationship

Indexed keywords

EID: 77955100673     PISSN: 10635823     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1063-5823(10)66010-3     Document Type: Chapter

References (74)

1. 2+ release mediated by type-1, -2 and -3 inositol trisphosphate receptors. The Biochemical Journal 2000, 345:357-363.
2. 2+ . Current Biology 1999, 9:1115-1118.
3. Adkins C.E., Wissing F., Potter B.V.L., Taylor C.W. Rapid activation and partial inactivation of inositol trisphosphate receptors by adenophostin A. The Biochemical Journal 2000, 352:929-933.
4. Beecroft M.D., Marchant J.S., Riley A.M., Van Straten N.C.R., Van der Marel G.A., Van Boom J.H., et al. Acyclophostin: A ribose-modified analog of adenophostin A with high affinity for inositol 1,4,5-trisphosphate receptors and pH-dependent efficacy. Molecular Pharmacology 1999, 55:109-117.
5. 3 R: Differing ATP sensitivities and molecular determinants of action. The Journal of Biological Chemistry 2008, 283:21579-21587.
6. Biot C., Buisine E., Kwasigroch J.-M., Wintgens R., Rooman M. Probing the energetic and structural role of amino acid/nucleobase cation-π interactions in protein-ligand complexes. The Journal of Biological Chemistry 2002, 277:40816-40822.
7. Bird G.S.J., Takahashi M., Tanzawa K., Putney J.W.J. Adenophostin A induces spatially restricted calcium signaling in Xenopus laevis occytes. The Journal of Biological Chemistry 1999, 274:20643-20649.
8. Borissow C.N., Black S.J., Paul M., Tovey S.C., Dedos S.G., Taylor C.W., et al. Adenophostin A and analogues modified at the adenine moiety: Synthesis, conformational analysis and biological activity. Organic & Biomolecular Chemistry 2005, 3:245-252.
9. Bosanac I., Alattia J.-R., Mal T.K., Chan J., Talarico S., Tong F.K., et al. Structure of the inositol 1,4,5-trisphosphate receptor binding core in complex with its ligand. Nature 2002, 420:696-700.
10. 2+ or egg activation. Developmental Biology 2000, 223:251-265.
11. CRAC . The Journal of Biological Chemistry 1999, 274:32881-32888.
12. Chan J., Whitten A.E., Jeffries C.M., Bosanac I., Mal T.K., Ito J., et al. Ligand-induced conformational changes via flexible linkers in the amino-terminal region of the inositol 1,4,5-trisphosphate receptor. Journal of Molecular Biology 2007, 373:1269-1280.
13. Chrétien F., Moitessier N., Roussel F., Mauger J.-P., Chapleur Y. Carbohydrate-based mimics of d-myo-inositol 1,4,5-trisphosphate. Current Organic Chemistry 2000, 4:513-534.
14. Correa V., Riley A.M., Shuto S., Horne G., Nerou E.P., Marwood R.D., et al. Structural determinants of adenophostin A activity at inositol trisphosphate receptors. Molecular Pharmacology 2001, 59:1206-1215.
15. de Kort M., Correa V., Valentijn A.R.P.M., van der Marel G.A., Potter B.V.L., Taylor C.W., et al. Synthesis of potent agonists of the d-myo-inositol 1,4,5-trisphosphate receptor based on clustered disaccharide polyphosphate analogs of adenophostin A. Journal of Medicinal Chemistry 2000, 43:3295-3303.
16. de Kort M., Regenbogen A.D., Overleeft H.S., Challis R.A.J., Iwata Y., Miyamoto S., et al. Synthesis and biological evaluation of cyclophostin A 5', 6''-tethered analog of adenophostin. Tetrahedron 2000, 56:5915-5928.
17. 2+ stores in the Xenopus oocyte. The Journal of Biological Chemistry 1997, 272:9956-9961.
18. 3 receptors. Science 2006, 313:229-233.
19. 3 receptor ligand. Molecular Pharmacology 2010, 77:995-1004.
20. Felemez M., Marwood R.D., Potter B.V., Spiess B. Inframolecular studies of the protonation of adenophostin A: Comparison with 1-d-myo-inositol 1,4,5-trisphosphate. Biochemical and Biophysical Research Communications 1999, 266:334-340.
21. Glouchankova L., Krishna U.M., Potter B.V.L., Falck J.R., Bezprozvanny I. Association of the inositol-(1,4,5) trisphosphate receptor ligand binding site with phosphatidylinositol (4, 5)-bisphosphate and adenophostin A. Molecular Cell Biology Research Communications 2000, 3:153-158.
22. 2+ inflow in rat hepatocytes. The Biochemical Journal 1999, 341:401-408.
23. - currents in Xenopus laevis oocytes. Molecular Pharmacology 1997, 51:683-692.
24. He C.L., Damiani P., Ducibella T., Takahashi M., Tanzawa K., Parys J.B., et al. Isoforms of the inositol 1,4,5-trisphosphate receptor are expressed in bovine oocytes and ovaries: The type-1 isoform is down-regulated by fertilization and by injection of adenophostin A. Biology of Reproduction 1999, 61:935-943.
25. 2+ release in the purified and reconstituted inositol 1,4,5-trisphosphate receptor type 1. FEBS Letters 1995, 368:248-252.
26. 2+ inducer, at the d-myo-inositol 1,4,5-trisphosphate receptor. Biochemistry 1999, 38:9234-9241.
27. 3 receptor ligand. 1: Synthesis of adenophostin A. Tetrahedon Letters 1995, 36:5037-5040.
28. crac ) in rat basophilic leukemia cells. The Journal of Biological Chemistry 1998, 273:31815-31821.
29. Jellerette T., He C.L., Wu H., Parys J.B., Fissore R.A. Down-regulation of the inositol-trisphosphate receptor in mouse eggs following fertilization or parthenogenetic activation. Developmental Biology 2000, 223:238-250.
30. Jenkins D.J., Marwood R.D., Potter B.V.L. A disaccharide polyphosphate mimic of 1d-myo-inositol 1,4,5-trisphosphate. Chemical Communications 1997, 5:449-450.
31. Jenkins D.J., Potter B.V.L. (2-Hydroxyethyl)-α-d-glucopyranoside-2',3,4-trisphosphate - synthesis of a second messenger mimic related to adenophostin A. Journal of Chemical Society, Chemical Communications 1995, 1169-1170.
32. 2+ release kinetics. The Journal of Biological Chemistry 1999, 274:4824-4831.
33. Mak D.-O., McBride S., Foskett J.K. ATP-dependent adenophostin activation of inositol 1,4,5-trisphosphate receptor channel gating. Kinetic implications for the duration of calcium puffs in cells. The Journal of General Physiology 2001, 117:299-314.
34. Marchant J.S., Beecroft M.D., Riley A.M., Jenkins D.J., Marwood R.D., Taylor C.W., et al. Disaccharide polyphosphates based upon adenophostin A activate hepatic d-myo-inositol 1,4,5-trisphosphate receptors. Biochemistry 1997, 36:12780-12790.
35. 3 receptor agonists. The Biochemical Journal 1998, 334:505-509.
36. Marchant J.S., Taylor C.W. Rapid activation and partial inactivation of inositol trisphosphate receptors by inositol trisphosphate. Biochemistry 1998, 37:11524-11533.
37. Marwood R.D., Correa V., Taylor C.W., Potter B.V.L. Synthesis of adenophostin A. Tetrahedron: Asymmetry 2000, 11:397-403.
38. Marwood R.D., Jenkins D.J., Correa V., Taylor C.W., Potter B.V.L. Contribution of the adenine base to the activity of adenophostin A investigated using a base replacement strategy. Journal of Medicinal Chemistry 2000, 43:4278-4287.
39. Marwood R.D., Riley A.M., Correa V., Taylor C.W., Potter B.V.L. Simplification of adenophostin A defines a minimal structure for potent glucopyranoside-based mimics of d-myo-inositol 1,4,5-trisphosphate. Bioorganic & Medicinal Chemistry Letters 1999, 9:453-458.
40. Marwood R.D., Riley A.M., Jenkins D.J., Potter B.V.L. Synthesis of adenophostin A and congeners modified at glucose. Journal of Chemical Society Perkin Transactions 2000, 1935-1947.
41. Marwood R.D., Shuto S., Jenkins D.J., Potter B.V.L. Convergent synthesis of adenophostin analogues via a base replacement strategy. Chemical Communications 2000, 219-220.
42. Mecozzi S., West A.P., Dougherty D.A. Cation-π interactions in aromatics of biological and medicinal interest: Electrostatic potential surfaces as a useful qualitative guide. Proceedings of the National Academy of Sciences of the United States of America 1996, 93:10566-10571.
43. 3 receptor in 16HBE14o- bronchial mucosal cells. The Journal of Biological Chemistry 1998, 273:8983-8986.
44. 3 receptor ligands. Journal of Medicinal Chemistry 2006, 49:5750-5758.
45. Morris S.A., Nerou E.P., Riley A.M., Potter B.V.L., Taylor C.W. Determinants of adenophostin A binding to inositol trisphosphate receptors. The Biochemical Journal 2002, 367:113-120.
46. Murphy C.T., Riley A.M., Lindley C.J., Westwick J., Potter B.V.L. Structural analogues of d-myo-inositol-1,4,5-trisphosphate and adenophostin A: Recognition by cerebellar and platelet inositol-1,4,5-trisphosphate receptors. Molecular Pharmacology 1997, 52:741-748.
47. Nerou E.P., Riley A.M., Potter B.V.L., Taylor C.W. Selective recognition of inositol phosphates by subtypes of inositol trisphosphate receptor. The Biochemical Journal 2001, 355:59-69.
48. Parekh A.B., Putney J.W. Store-operated calcium channels. Physiological Reviews 2005, 85:757-810.
49. 2+ buffer. The Biochemical Journal 2002, 361:133-141.
50. Park C.Y., Hoover P.J., Mullins F.M., Bachhawat P., Covington E.D., Raunser S., et al. STIM1 clusters and activates CRAC channels via direct binding of a cytosolic domain to Orai1. Cell 2009, 136:876-890.
51. 2+ . Nature 2009, 458:655-659.
52. 3 receptor interaction. Journal of Medicinal Chemistry 2003, 46:4860-4871.
53. Rosenberg H.J., Riley A.M., Marwood R.D., Correa V., Taylor C.W., Potter B.V.L. Xylopyranoside-based agonists of d-myo-inositol 1,4,5-trisphosphate receptors: Synthesis and effect of stereochemistry on biological activity. Carbohydrate Research 2001, 332:53-66.
54. Rossi, A., Sureshan, K. M., Riley, A. M., Potter, B. V. L., Taylor, C. W. (2010) Selective determinants of IP3 and adenophostin A interactions with type 1 IP3 receptors. British Journal of Pharmalogy, in press.
55. 3 receptor activation. Nature Chemical Biology 2009, 5:631-639.
56. Sato Y., Miyazaki S., Shikano T., Mitsuhashi N., Takeuchi H., Mikoshiba K., et al. 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 offspring. Biology of Reproduction 1998, 58:867-873.
57. Shuto S., Horne G., Marwood R.D., Potter B.V.L. Total synthesis of nucleobase-modified adenophostin A mimics. Chemistry A. European Journal 2001, 7:4937-4946.
58. 3 receptor ligands: Some structural requirements for the significant activity of adenophostin A. The Journal of Organic Chemistry 1998, 63:8815-8824.
59. 2+ puffs in intact mammalian cells. Proceedings of the National Academy of Sciences of the United States of America 2009, 106:6404-6409.
60. 3 receptors by synthetic bisphosphate ligands. Chemical Communications 2009, 14:1204-1206.
61. Sureshan K.M., Trusselle M., Tovey S.C., Taylor C.W., Potter B.V.L. Guanophostin A: Synthesis and evaluation of a high affinity agonist of the d-myo-inositol 1,4,5-trisphosphate receptor. Chemical Communications 2006, 19:2015-2017.
62. Sureshan K.M., Trusselle M., Tovey S.C., Taylor C.W., Potter B.V.L. 2-Position base-modified analogues of adenophostin A as high-affinity agonists of the d-myo-inositol trisphosphate receptor: In vitro evaluation and molecular modeling. The Journal of Organic Chemistry 2008, 73:1682-1692.
63. Swatton J.E., Morris S.A., Taylor C.W. Functional properties of Drosophila inositol trisphosphate receptors. The Biochemical Journal 2001, 359:435-441.
64. Takahashi M., Kagasaki T., Hosoya T., Takahashi S. Adenophostins A and B: Potent agonists of inositol-1,4,5-trisphosphate receptor produced by Penicillium brevicompactum. Taxonomy, fermentation, isolation, physico-chemical and biological properties. The Journal of Antibiotics 1994, 46:1643-1647.
65. Takahashi M., Tanzawa K., Takahashi S. Adenophostins, newly discovered metabolites of Penicillium brevicompactum, act as potent agonists of the inositol 1,4,5-trisphosphate receptor. The Journal of Biological Chemistry 1994, 269:369-372.
66. Takahashi S., Takeshi K., Takahashi M. Adenophostins A and B: Potent agonists of inositol-1,4,5-trisphosphate receptors produced by Penicillium brevicompactum. Structure elucidation. The Journal of Antibiotics 1994, 47:95-100.
67. 3 receptors: The search for structure. Trends in Biochemical Sciences 2004, 29:210-219.
68. Turner H., Fleig A., Stokes A., Kinet J.-P., Penner R. Discrimination of intracellular calcium store subcompartments using TRPV1 (transient receptor potential channel, vanilloid subfamily member 1) release channel activity. The Biochemical Journal 2003, 371:341-350.
69. 3 receptor isoforms. The Biochemical Journal 2000, 346:275-280.
70. Van Straten N.C.R., Van der Marel G.A., Van Boom J.H. An expeditious route to the synthesis of adenophostin A. Tetrahedron 1997, 53:6509-6522.
71. Van Straten N.C.R., Van der Marel G.A., Van Boom J.H. Synthesis of 2',3'',4''-trisphosphate-containing analogues of adenophostin A. Tetrahedron 1997, 53:6523-6538.
72. Wilcox R.A., Erneux C., Primrose W.U., Gigg R., Nahorski S.R. 2-Hydroxy-α-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. Molecular Pharmacology 1995, 47:1204-1211.
73. Wilcox R.A., Primrose W.U., Nahorski S.R., Challiss R.A.J. New developments in the molecular pharmacology of the myo-inositol 1,4,5-trisphosphate receptor. Trends in Pharmacological Sciences 1998, 19:467-475.
74. 2+ oscillations in activation of ascidian eggs. Developmental Biology 1998, 203:122-133.