Synthesis and pharmacological evaluation of novel thromboxane modulators as antiplatelet agents acting on both the alpha and beta isoforms of the human thromboxane receptor
Hanson, Julien; Reynaud, Denis; Qiao, Naet al.
2006 • In Journal of Medicinal Chemistry, 49 (12), p. 3701-3709
Synthesis and pharmacological evaluation of novel thromboxane modulators as antiplatelet agents acting on both the alpha and beta isoforms of the human thromboxane receptor
Publication date :
June 2006
Journal title :
Journal of Medicinal Chemistry
ISSN :
0022-2623
eISSN :
1520-4804
Publisher :
American Chemical Society, Washington, United States - District of Columbia
Hamberg, M.; Svensson, J.; Samuelsson, B. Thromboxanes: a new group of biologically active compounds derived from prostaglandin endoperoxides. Proc. Natl. Acad. Sci. U.S.A. 1975, 72, 2994-2998.
Moncada, S.; Ferreira, S. H.; Vane, J. R. Bioassay of prostaglandins and biologically active substances derived from arachidonic acid. Adv. Prostaglandin. Thromboxane. Res. 1978, 5, 211-236.
Dogne, J. M.; de Leval, X.; Hanson, J.; Frederich, M.; Lambermont, B. et al. New developments on thromboxane and prostacyclin modulators part I: thromboxane modulators. Curr. Med. Chem. 2004, 11, 1223-1241.
Cheng, Y.; Austin, S. C.; Rocca, B.; Koller, B. H.; Coffman, T. M. et al. Role of prostacyclin in the cardiovascular response to thromboxane A2. Science 2002, 296, 539-541.
Coleman, R. A.; Smith, W. L.; Narumiya, S. International Union of Pharmacology classification of prostanoid receptors: properties, distribution, and structure of the receptors and their subtypes. Pharmacol. Rev. 1994, 46, 205-229.
Hirata, M.; Hayashi, Y.; Ushikubi, F.; Yokota, Y.; Kageyama, R. et al. Cloning and expression of cDNA for a human thromboxane A2 receptor. Nature 1991, 349, 617-620.
Raychowdhury, M. K.; Yukawa, M.; Collins, L. J.; McGrail, S. H.; Kent, K. C. et al. Alternative splicing produces a divergent cytoplasmic tail in the human endothelial thromboxane A2 receptor. J. Biol. Chem. 1994, 269, 19256-19261.
Mais, D. E.; Saussy, D. L., Jr.; Chaikhouni, A.; Kochel, P. J.; Knapp, D. R. et al. Pharmacologic characterization of human and canine thromboxane A2/prostaglandin H2 receptors in platelets and blood vessels: evidence for different receptors. J. Pharmacol. Exp. Ther. 1985, 233, 418-424.
Qiao, N.; Reynaud, D.; Demin, P.; Halushka, P. V.; Pace-Asciak, C. R. The thromboxane receptor antagonist PBT-3, a hepoxilin stable analogue, selectively antagonizes the TPalpha isoform in transfected COS-7 cells. J. Pharmacol. Exp. Ther. 2003, 307, 1142-1147.
Coyle, A. T.; Kinsella, B. T. Characterization of promoter 3 of the human thromboxane A receptor gene. A functional AP-1 and octamer motif are required for basal promoter activity. FEBS J. 2005, 272, 1036-1053.
Coyle, A. T.; O'Keeffe, M. B.; Kinsella, B. T. 15-deoxy Delta12, 14-prostaglandin J2 suppresses transcription by promoter 3 of the human thromboxane A2 receptor gene through peroxisome proliferator-activated receptor gamma in human erythroleukemia cells. FEBS J. 2005, 272, 4754-4773.
Ashton, A. W.; Ware, J. A. Thromboxane A2 receptor signaling inhibits vascular endothelial growth factor-induced endothelial cell differentiation and migration. Circ. Res. 2004, 95, 372-379.
Habib, A.; FitzGerald, G. A.; Maclouf, J. Phosphorylation of the thromboxane receptor alpha, the predominant isoform expressed in human platelets. J. Biol. Chem. 1999, 274, 2645-2651.
Reid, H. M.; Kinsella, B. T. The alpha, but not the beta, isoform of the human thromboxane A2 receptor is a target for nitric oxide-mediated desensitization. Independent modulation of Tp alpha signaling by nitric oxide and prostacyclin. J. Biol. Chem. 2003, 278, 51190-51202.
Egan, K. M.; Wang, M.; Fries, S.; Lucitt, M. B.; Zukas, A. M. et al. Cyclooxygenases, thromboxane, and atherosclerosis: plaque destabilization by cyclooxygenase-2 inhibition combined with thromboxane receptor antagonism. Circulation 2005, 111, 334-342.
Dogne, J. M.; Supuran, C. T.; Pratico, D. Adverse cardiovascular effects of the coxibs. J. Med. Chem. 2005, 48, 2251-2257.
Meerwein, H.; Dittmar, G.; Gollner, R.; Hafner, K.; Mensch, F. et al. Aromatic diazo compounds. 11. Preparation of aromatic sulfonyl chlorides, a new modification of the Sandmeyer reaction. Chem. Ber. 1957, 90, 841-852.
Dogne, J. M.; Hanson, J.; de Leval, X.; Kolh, P.; Tchana-Sato, V. et al. Pharmacological characterization of N-tert-butyl-N′-[2-(4′- methylphenylamino)-5-nitrobenzenesulfonyl]urea (BM-573), a novel thromboxane A2 receptor antagonist and thromboxane synthase inhibitor in a rat model of arterial thrombosis and its effects on bleeding time. J. Pharmacol. Exp. Ther. 2004, 309, 498-505.
Ghuysen, A.; Lambermont, B.; Dogne, J. M.; Kolh, P.; Tchana-Sato, V. et al. Effect of BM-573 [N-terbutyl-N′-[2-(4′-methylphenylamino)-5- nitro-benzenesulfonyl]urea], a dual thromboxane synthase inhibitor and thromboxane receptor antagonist, in a porcine model of acute pulmonary embolism. J. Pharmacol. Exp. Ther. 2004, 310, 964-972.
Rolin, S.; Petein, M.; Tchana-Sato, V.; Dogne, J. M.; Benoit, P. et al. BM-573, a dual thromboxane synthase inhibitor and thromboxane receptor antagonist, prevents pig myocardial infarction induced by coronary thrombosis. J. Pharmacol. Exp. Ther. 2003, 306, 59-65.
Tchana-Sato, V.; Dogne, J. M.; Lambermont, B.; Ghuysen, A.; Magis, D. et al. Effects of BM-573, a thromboxane A2 modulator on systemic hemodynamics perturbations induced by U-46619 in the pig. Prostaglandins Other Lipid Mediat. 2005, 78, 82-95.
Hanson, J.; Rolin, S.; Reynaud, D.; Qiao, N.; Kelley, L. P. et al. In vitro and in vivo pharmacological characterization of BM-613 [N-n-pentyl-N′-[2-(4′-methylphenylamino)-5-nitrobenzenesulfonyl] urea], a novel dual thromboxane synthase inhibitor and thromboxane receptor antagonist. J. Pharmacol. Exp. Ther. 2005, 313, 293-301.
Parent, J. L.; Labrecque, P.; Orsini, M. J.; Benovic, J. L. Internalization of the TXA2 receptor alpha and beta isoforms. Role of the differentially spliced cooh terminus in agonist-promoted receptor internalization. J. Biol. Chem. 1999, 274, 8941-8948.
Kinsella, B. T.; O'Mahony, D. J.; Fitzgerald, G. A. The human thromboxane A2 receptor alpha isoform (TP alpha) functionally couples to the G proteins Gq and G11 in vivo and is activated by the isoprostane 8-epi prostaglandin F2 alpha. J. Pharmacol. Exp. Ther. 1997, 281, 957-964.
Walsh, M. T.; Foley, J. F.; Kinsella, B. T. Characterization of the role of N-linked glycosylation on the cell signaling and expression of the human thromboxane A2 receptor alpha and beta isoforms. J. Pharmacol. Exp. Ther. 1998, 286, 1026-1036.
Dogne, J. M.; Wouters, J.; Rolin, S.; Michaux, C.; Pochet, L. et al. Design, synthesis and biological evaluation of a sulfonylcyanoguanidine as thromboxane A2 receptor antagonist and thromboxane synthase inhibitor. J. Pharm. Pharmacol. 2001, 53, 669-680.
Wagner, A. W.; Banholzer, R. Heterocycles with endocyclic sulfur-nitrogen double bond. I. 1-Substituted 5-nitro-1H-1,3,2-benzodithiazole 3,3-dioxides. Berichte 1963, 96, 1177-1186.
Walsh, M. T.; Foley, J. F.; Kinsella, B. T. The alpha, but not the beta, isoform of the human thromboxane A2 receptor is a target for prostacyclin-mediated desensitization. J. Biol. Chem. 2000, 275, 20412-20423.
Lin, K.; Sadee, W.; Quillan, J. M. Rapid measurements of intracellular calcium using a fluorescence plate reader. Biotechniques 1999, 26, 318-322, 324-316.
Born, G. V.; Cross, M. J. The Aggregation of Blood Platelets. J. Physiol 1963, 168, 178-195.
Dogne, J. M.; de Leval, X.; Neven, P.; Rolin, S.; Wauters, J. et al. Effects of a novel non-carboxylic thromboxane A2 receptor antagonist (BM-531) derived from torasemide on platelet function. Prostaglandins. Leukotrienes Essent. Fatty Acids 2000, 62, 311-317.
Harris, D. N.; Asaad, M. M.; Phillips, M. B.; Goldenberg, H. J.; Antonaccio, M. J. Inhibition of adenylate cyclase in human blood platelets by 9-substituted adenine derivatives. J. Cyclic Nucleotide Res. 1979, 5, 125-134.