Binding and activity of the prostacyclin receptor (IP) agonists, treprostinil and iloprost, at human prostanoid receptors: Treprostinil is a potent DP 1 and EP 2 agonist

Biochemical Pharmacology

Volumn 84, Issue 1, 2012, Pages 68-75

  Whittle, Brendan J ^a   Silverstein, Adam M ^b   Mottola, David M ^b   Clapp, Lucie H ^c  

^a QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

^b UNITED THERAPEUTICS CORPORATION   (United States)

^c UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

Calcium influx; Cyclic AMP; Prostacyclin analogues; Prostanoid receptors; Radioligand binding

Indexed keywords

CYCLIC AMP; ILOPROST; PROSTACYCLIN RECEPTOR; PROSTAGLANDIN E RECEPTOR 1; PROSTAGLANDIN E RECEPTOR 2; PROSTAGLANDIN E RECEPTOR 3; PROSTAGLANDIN E RECEPTOR 4; PROSTANOID RECEPTOR; UNIPROST;

ARTICLE; BINDING AFFINITY; BINDING ASSAY; CALCIUM TRANSPORT; DRUG ACTIVITY; DRUG POTENCY; DRUG RECEPTOR BINDING; HUMAN; HUMAN CELL; IN VITRO STUDY; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PULMONARY ARTERY; VASOCONSTRICTION; VASODILATATION;

ANTIHYPERTENSIVE AGENTS; BINDING, COMPETITIVE; CALCIUM; CELL CULTURE TECHNIQUES; CYCLIC AMP; EPOPROSTENOL; HEK293 CELLS; HUMANS; HYPERTENSION, PULMONARY; ILOPROST; RADIOLIGAND ASSAY; RECEPTORS, PROSTAGLANDIN; RECEPTORS, PROSTAGLANDIN E, EP2 SUBTYPE; TRANSFECTION;

EID: 84860659739     PISSN: 00062952     EISSN: 18732968     Source Type: Journal    
DOI: 10.1016/j.bcp.2012.03.012     Document Type: Article

References (60)

1. L.J. Rubin, B.M. Groves, J.T. Reeves, M. Frosolono, F. Handel, and A.E. Cato Prostacyclin-induced acute pulmonary vasodilation in primary pulmonary hypertension Circulation 66 1982 334 338
2. R.J. Barst, L.J. Rubin, W.A. Long, M.D. McGoon, S. Rich, and D.B. Badesch A comparison of continuous intravenous epoprostenol (prostacyclin) with conventional therapy for primary pulmonary hypertension. The Primary Pulmonary Hypertension Study Group N Engl J Med 334 1996 296 302
3. R. Barst How has epoprostenol changed the outcome for patients with pulmonary arterial hypertension Int J Clin Pract Suppl 2010 23 32
4. Z. Safdar Treatment of pulmonary arterial hypertension: the role of prostacyclin and prostaglandin analogs Respir Med 105 2011 818 827
5. B.J.R. Whittle, S. Moncada, and J.R. Vane Biological activities of some metabolites and analogues of prostacyclin F.G. De Las Heras, S. Vega, Medicinal chemistry advances 1981 Pergamon Press Oxford 141 158
6. B.J.R. Whittle, and S. Moncada Antithrombotic assessment and clinical potential of prostacyclin analogues G.P. Ellis, G.B. West, Progress in medical chemistry 1984 Elsevier Science Publishers North Holland 237 279
7. H. Olschewski, F. Rose, R. Schermuly, H.A. Ghofrani, B. Enke, and A. Olschewski Prostacyclin and its analogues in the treatment of pulmonary hypertension Pharmacol Ther 102 2004 139 153
8. M. Murakami, M. Watanabe, H. Furukawa, and H. Nakahara The prostacyclin analogue beraprost sodium prevents occlusion of bypass grafts in patients with lower extremity arterial occlusive disease: a 20-year retrospective study Ann Vasc Surg 19 2005 838 842
9. S. Berman, R. Quick, P. Yoder, S. Voigt, D. Strootman, and M. Wade Treprostinil sodium (Remodulin), a prostacyclin analog, in the treatment of critical limb ischemia: open-label study Vascular 14 2006 142 148
10. B. Fernandez, and D. Strootman The prostacyclin analog, treprostinil sodium, provides symptom relief in severe Buerger's disease - a case report and review of literature Angiology 57 2006 99 102
11. A. Kawald, G.R. Burmester, D. Huscher, C. Sunderkotter, and G. Riemekasten Low versus high-dose iloprost therapy over 21 days in patients with secondary Raynaud's phenomenon and systemic sclerosis: a randomized, open, single-center study J Rheumatol 35 2008 1830 1837
12. 2 analog, improves renal anemia in hemodialysis patients with peripheral arterial disease Ther Apher Dial 14 2010 472 476
13. A. Piaggesi, V. Vallini, E. Iacopi, A. Tedeschi, A. Scatena, and C. Goretti Iloprost in the management of peripheral arterial disease in patients with diabetes mellitus Minerva Cardioangiol 59 2011 101 108
14. M.M. Hoeper, M. Schwarze, S. Ehlerding, A. Adler-Schuermeyer, E. Spiekerkoetter, and J. Niedermeyer Long-term treatment of primary pulmonary hypertension with aerosolized iloprost, a prostacyclin analogue N Engl J Med 342 2000 1866 1870
15. G. Simonneau, R.J. Barst, N. Galie, R. Naeije, S. Rich, and R.C. Bourge Continuous subcutaneous infusion of treprostinil, a prostacyclin analogue, in patients with pulmonary arterial hypertension: a double-blind, randomized, placebo-controlled trial Am J Respir Crit Care Med 165 2002 800 804
16. M. Gomberg-Maitland, and H. Olschewski Prostacyclin therapies for the treatment of pulmonary arterial hypertension Eur Respir J 31 2008 891 901
17. N. Skoro-Sajer, I. Lang, and R. Naeije Treprostinil for pulmonary hypertension Vasc Health Risk Manage 4 2008 507 513
18. J.L. Vachiery Prostacyclins in pulmonary arterial hypertension: the need for earlier therapy Adv Ther 28 2011 251 269
19. T. Hirata, and S. Narumiya Prostanoid receptors Chem Rev 111 2011 6209 6230
20. I. Kennedy, R.A. Coleman, P.P. Humphrey, G.P. Levy, and P. Lumley Studies on the characterisation of prostanoid receptors: a proposed classification Prostaglandins 24 1982 667 689
21. M. Abramovitz, M. Adam, Y. Boie, M. Carriere, D. Denis, and C. Godbout The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs Biochim Biophys Acta 1483 2000 285 293
22. R.A. Coleman, P.P.A. Humphrey, I. Kennedy, and P. Lumley Prostanoid receptors - the development of a working class classification Trends Pharmacol Sci 5 1984 303 306
23. R.A. Coleman, I. Kennedy, P.P.A. Humphrey, K. Bunce, and P. Lumley Prostanoids and their receptors C. Hansch, P.G. Samnes, J.B. Taylor, Comprehensive medicinal chemistry 1990 Pergamon Press Oxford 643 714
24. D.F. Woodward, R.L. Jones, and S. Narumiya International union of basic and clinical pharmacology. LXXXIII: Classification of prostanoid receptors, updating 15 years of progress Pharmacol Rev 63 2011 471 538
25. R.A. Coleman, W.L. Smith, and S. Narumiya International union of pharmacology classification of prostanoid receptors: properties, distribution, and structure of the receptors and their subtypes Pharmacol Rev 46 1994 205 229
26. S.M. Wilson, N.A. Sheddan, R. Newton, and M.A. Giembycz Evidence for a second receptor for prostacyclin on human airway epithelial cells that mediates inhibition of CXCL9 and CXCL10 release Mol Pharmacol 79 2011 586 595
27. 2-sensitive adenylate cyclase in human platelet membranes Prostaglandins 27 1984 321 333
28. E. Falcetti, D.M. Flavell, B. Staels, A. Tinker, S.G. Haworth, and L.H. Clapp IP receptor-dependent activation of PPARγ by stable prostacyclin analogues Biochem Biophys Res Commun 360 2007 821 827
29. E. Falcetti, S.M. Hall, P.G. Phillips, J. Patel, N.W. Morrell, and S.G. Haworth Smooth muscle proliferation and role of the prostacyclin (IP) receptor in idiopathic pulmonary arterial hypertension Am J Respir Crit Care Med 182 2010 1161 1170
30. K. Kuwano, A. Hashino, T. Asaki, T. Hamamoto, T. Yamada, and K. Okubo 2-[4-[(5,6-Diphenylpyrazin-2-yl)(isopropyl)amino]butoxy]-N-(methylsulfonyl) acetamide (NS-304), an orally available and long-acting prostacyclin receptor agonist prodrug J Pharmacol Exp Ther 322 2007 1181 1188
31. K. Morrison, R. Ernst, P. Hess, R. Studer, and M. Clozel Selexipag: a selective prostacyclin receptor agonist that does not affect rat gastric function J Pharmacol Exp Ther 335 2010 249 255
32. L.H. Clapp, and J.M. Patel The mechanistic basis for prostacyclin action in pulmonary hypertension Int J Respir Care 2010 27 33
33. M. Kiriyama, F. Ushikubi, T. Kobayashi, M. Hirata, Y. Sugimoto, and S. Narumiya Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells Br J Pharmacol 122 1997 217 224
34. D.H. Wright, K.M. Metters, M. Abramovitz, and A.W. Ford-Hutchinson Characterization of the recombinant human prostanoid DP receptor and identification of L-644,698, a novel selective DP agonist Br J Pharmacol 123 1998 1317 1324
35. N.A. Sharif, and T.L. Davis Cloned human EP1 prostanoid receptor pharmacology characterized using radioligand binding techniques J Pharm Pharmacol 54 2002 539 547
36. N.A. Sharif, J.Y. Crider, S.X. Xu, and G.W. Williams Affinities, selectivities, potencies, and intrinsic activities of natural and synthetic prostanoids using endogenous receptors: focus on DP class prostanoids J Pharmacol Exp Ther 293 2000 321 328
37. 1 prostanoid receptor Mol Pharmacol 59 2001 1446 1456
38. Y.J. Dong, R.L. Jones, and N.H. Wilson Prostaglandin E receptor subtypes in smooth muscle: agonist activities of stable prostacyclin analogues Br J Pharmacol 87 1986 97 107
39. R.A. Armstrong, R.A. Lawrence, R.L. Jones, N.H. Wilson, and A. Collier Functional and ligand binding studies suggest heterogeneity of platelet prostacyclin receptors Br J Pharmacol 97 1989 657 668
40. 4 receptors Eur J Pharmacol 501 2004 49 58
41. Y. Boie, N. Sawyer, D.M. Slipetz, K.M. Metters, and M. Abramovitz Molecular cloning and characterization of the human prostanoid DP receptor J Biol Chem 270 1995 18910 18916
42. 3H]-BWA868C, a DP receptor-selective antagonist radioligand Br J Pharmacol 131 2000 1025 1038
43. D.M. Aronoff, C.M. Peres, C.H. Serezani, M.N. Ballinger, J.K. Carstens, and N. Coleman Synthetic prostacyclin analogs differentially regulate macrophage function via distinct analog-receptor binding specificities J Immunol 178 2007 1628 1634
44. M. Abramovitz, M. Adam, Y. Boie, R. Grygorczyk, T.H. Rushmore, and T. Nguyen Human prostanoid receptors: cloning and characterization Adv Prostaglandin Thromboxane Leukot Res 23 1995 499 504
45. B.J.R. Whittle, S. Hamid, P. Lidbury, and A.C. Rosam Specificity between anti-aggregatory actions of prostacyclin, prostaglandin E1 and D2 on platelets J. Westwick, Mechanisms of stimulus secretion coupling in platelets 1985 Plenum Press New York 109 125
46. H. Giles, P. Leff, M.L. Bolofo, M.G. Kelly, and A.D. Robertson The classification of prostaglandin DP-receptors in platelets and vasculature using BW A868C, a novel, selective and potent competitive antagonist Br J Pharmacol 96 1989 291 300
47. L. Walch, C. Labat, J.P. Gascard, M. de, V. Brink C, and X. Norel Prostanoid receptors involved in the relaxation of human pulmonary vessels Br J Pharmacol 126 1999 859 866
48. 4 receptor subtype Br J Pharmacol 154 2008 1631 1639
49. L. Walch, V. de Montpreville, C. Brink, and X. Norel Prostanoid EP1 and TP-receptors involved in the contraction of human pulmonary veins Br J Pharmacol 134 2001 1671 1678
50. 3 receptor agonists on human isolated pulmonary artery Br J Pharmacol 113 1994 369 374
51. K. Kuwano, A. Hashino, K. Noda, K. Kosugi, and K. Kuwabara A long-acting and highly selective prostacyclin receptor agonist prodrug, 2-{4-[(5,6- diphenylpyrazin-2-yl)(isopropyl)amino]butoxy}-N-(methylsulfonyl)acetamide (NS-304), ameliorates rat pulmonary hypertension with unique relaxant responses of its active form, {4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy}acetic acid (MRE-269), on rat pulmonary artery J Pharmacol Exp Ther 326 2008 691 699
52. + channels play a major role in mediating the vascular effects of iloprost and cicaprost Eur J Pharmacol 356 1998 215 224
53. C. McCormick, R.L. Jones, S. Kennedy, and R.M. Wadsworth Activation of prostanoid EP receptors by prostacyclin analogues in rabbit iliac artery: implications for anti-restenotic potential Eur J Pharmacol 641 2010 160 167
54. N.N. Orie, and L.H. Clapp Role of prostanoid IP and EP receptors in mediating vasorelaxant responses to PGI2 analogues in rat tail artery: evidence for Gi/o modulation via EP3 receptors Eur J Pharmacol 654 2011 258 265
55. 4 prostanoid receptor-mediated vasodilatation of human middle cerebral arteries Br J Pharmacol 141 2004 580 585
56. X. Norel Prostanoid receptors in the human vascular wall ScientificWorldJournal 7 2007 1359 1374
57. L.H. Clapp, P.A. Finney, S. Turcato, S. Tran, L.J. Rubin, and A. Tinker Differential effects of stable prostacyclin analogues on smooth muscle proliferation and cyclic AMP generation in human pulmonary artery Am J Respir Cell Mol Biol 26 2002 194 201
58. 4 receptor in iloprost-mediated vasodilatation in pulmonary hypertension Am J Respir Crit Care Med 178 2008 188 196
59. W. Krause, and T. Krais Pharmacokinetics and pharmacodynamics of the prostacyclin analogue iloprost in man Eur J Clin Pharmacol 30 1986 61 68
60. C.S. McSwain, R. Benza, S. Shapiro, N. Hill, R. Schilz, and C.G. Elliott Dose proportionality of treprostinil sodium administered by continuous subcutaneous and intravenous infusion J Clin Pharmacol 48 2008 19 25