Roles of affinity and lipophilicity in the slow kinetics of prostanoid receptor antagonists on isolated smooth muscle preparations

British Journal of Pharmacology

Volumn 162, Issue 4, 2011, Pages 863-879

  Jones, R L ^a   Woodward, D F ^b   Wang, J W ^b   Clark, R L ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b ALLERGAN INC   (United States)

Author keywords

antagonist inhibition curve protocol; BMS 180291; FLIPR assay; isolated smooth muscle preparation; L 798106; L 826266; limited diffusion model; lipophilicity; plasmalemmal diffusion microkinetic model; prostanoid EP 3 receptor; prostanoid TP receptor

Indexed keywords

1 (3 METHOXYBENZYL) 3A METHYL 3,3A,4,5,6 HEXAHYDROINDOL 2 ONE 7 ACRYLIC ACID 3,4 DIFLUOROBENZENESULFONAMIDE; 1 DECARBOXY 11 DEOXY 16,16 DIFLUORO 16 PHENYL OMEGA TETRANOR 1 (5 TETRAZOLO)PROSTAGLANDIN E1; 15 HYDROXY 11ALPHA,9ALPHA EPOXYMETHANOPROSTA 5,13 DIENOIC ACID; 16,16 DIMETHYLPROSTAGLANDIN E2; 16,16 DIMETHYLPROSTAGLANDIN F2 ALPHA; 3 BENZYL 5 (6 CARBOXYHEXYL) 1 (2 CYCLOHEXYL 2 HYDROXYETHYLAMINO)HYDANTOIN; 5 (6 CARBOXYHEXYL) 1 (3 CYCLOHEXYL 3 HYDROXYPROPYL)HYDANTOIN; 6 [2 (2 CHLOROPHENYL) 4 (2 HYDROXYPHENYL) 1,3 DIOXAN 5 YL] 4 HEXENOIC ACID; 7 (3 ACETYLBICYCLO[2.2.1]HEPT 2 YL) 5 HEPTENOIC ACID 4 PHENYLTHIOSEMICARBAZONE; 7 (3 FORMYLBICYCLO[2.2.1]HEPT 2 YL) 5 HEPTENOIC ACID 4 PHENYLSEMICARBAZONE; 7 [3 [(4 PHENYLSEMICARBAZIDO)METHYL] 7 OXABICYCLO[2.2.1]HEPT 2 YL] 5 HEPTENOIC ACID; ASTEMIZOLE; ATROPINE; CARBACYCLIN; CICAPROST; CLOPROSTENOL; DG 3AP; IFETROBAN; L 798106; L 826266; L 902688; LAROPIPRANT; LATANOPROST; N [(5 BROMO 2 METHOXYPHENYL)SULFONYL] 3 [2 (2 NAPHTHYLMETHYL)PHENYL]ACRYLAMIDE; N [(5 BROMO 2 METHOXYPHENYL)SULFONYL] 3 [5 CHLORO 2 (2 NAPHTHYLMETHYL)PHENYL]ACRYLAMIDE; PROSTAGLANDIN E2; PROSTAGLANDIN F2 ALPHA; PROSTAGLANDIN RECEPTOR AFFECTING AGENT; PROSTANOID RECEPTOR; PROSTANOID RECEPTOR BLOCKING AGENT; PROSTANOID RECEPTOR STIMULATING AGENT; SULPROSTONE; TERFENADINE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL TISSUE; AORTA MEDIA; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; EMBRYO; GUINEA PIG; HUMAN; HUMAN CELL; LIPOPHILICITY; MALE; NONHUMAN; PRIORITY JOURNAL; VAS DEFERENS;

ACRYLAMIDES; ANIMALS; AORTA, THORACIC; GUINEA PIGS; HEK293 CELLS; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; ISOENZYMES; KINETICS; LIGANDS; MALE; MODELS, BIOLOGICAL; MUSCLE CONTRACTION; MUSCLE RELAXATION; MUSCLE, SMOOTH; NAPHTHALENES; NEUROMUSCULAR AGENTS; RECEPTORS, EICOSANOID; RECEPTORS, PROSTAGLANDIN E, EP3 SUBTYPE; RECOMBINANT PROTEINS; SULFONAMIDES; VAS DEFERENS;

EID: 79251513301     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1111/j.1476-5381.2010.01087.x     Document Type: Article

References (66)

1. Alexander SPH, Mathie A, Peters JA, (2009). Guide to Receptors and Channels (GRAC), 4th edn. Br J Pharmacol 158 (Suppl. 1): S1-S254.
2. 2-adrenoceptor agonist bronchodilator. Life Sci 52: 2145-2160.
3. Anderson GP, Lindén A, Rabe KF, (1994). Why are long-acting beta-adrenoceptor agonists long-acting? Eur Respir J 7: 569-578.
4. 2-adrenoceptor agonists. J Med Chem 46: 3210-3220.
5. 2. J Pharm Sci 84: 523-529.
6. 3 antagonists. Bioorg Med Chem Lett 15: 527-530.
7. 3 antagonists and their biological activities. Bioorg Med Chem Lett 16: 5639-5642.
8. Cao J, Shayibuzhati M, Tajima T, Kitazawa T, Taneike T, (2002). In vitro pharmacological characterization of the prostanoid receptor population in the non-pregnant porcine myometrium. Eur J Pharmacol 442: 115-123.
9. 1 receptor antagonism by cetirizine in isolated guinea pig tissues: influence of receptor reserve and dissociation kinetics. Eur J Pharmacol 470: 87-94.
10. 3-subtype. Br J Pharmacol 141: 600-609.
11. Coleman RA, (2009). On the mechanism of the persistent action of salmeterol: what is the current position? Br J Pharmacol 158: 180-182.
12. Coleman RA, Kennedy I, (1985). Characterisation of the prostanoid receptors mediating contraction of guinea-pig isolated trachea. Prostaglandins 29: 363-375.
13. 2-sensitive (EP) receptors. Adv Prostaglandin Thromboxane Leukot Res 17A: 467-470.
14. Colquhoun D, Ritchie JM, (1972). The kinetics of the interaction between tetrodotoxin and mammalian nonmyelinated nerve fibers. Mol Pharmacol 285: 285-292.
15. Colquhoun D, Henderson R, Ritchie JM, (1972). The binding of labelled tetrodotoxin to non-myelinated nerve fibres. J Physiol 227: 95-126.
16. Craig DA, (1993). The Cheng-Prusoff relationship: something lost in the translation. Trends Pharmacol Sci 14: 89-91.
17. Daray FM, Minvielle AI, Puppo S, Rothlin RP, (2003). Pharmacological characterization of prostanoid receptors mediating vasoconstriction in human umbilical vein. Br J Pharmacol 139: 1409-1426.
18. 1-receptors. Inflam Res 36 (Suppl. 2): C410-C413.
19. Fabre JE, Gurney ME, (2010). Limitations of current therapies to prevent thrombosis: a need for novel strategies. Mol Biosyst 6: 305-315.
20. Figueiredo A, Ribeiro CA, GonÃalo M, Almeida L, Poiares-Baptista A, Teixeira F, (1990). Mechanism of action of doxepin in the treatment of chronic urticaria. Fundam Clin Pharmacol 4: 147-158.
21. 4 receptor subtype. Br J Pharmacol 154: 1631-1639.
22. 3 prostanoid receptor. Bioorg Med Chem Lett 12: 2583-2586.
23. Giles H, Leff P, Bolofo ML, Kelly MG, Robertson AD, (1989). The classification of prostaglandin DP-receptors in platelets and vasculature using BW A868C, a novel, selective and potent competitive antagonist. Br J Pharmcol 96: 291-300.
24. Glass GV, Hopkins KD, (1996). Multiple comparisons and trend analysis. In: Statistical Methods in Education and Psychology. Allyn and Bacon: Boston, pp. 444-481.
25. Heptinstall S, Espinosa DI, Manolopoulos P, Glenn JR, White AE, Johnson A, et al. (2008). DG-041 inhibits the EP3 prostanoid receptor-a new target for inhibition of platelet function in atherosclerotic disease. Platelets 19: 605-613.
26. Ito Y, Tajima K, (1979). Electrophysiological analysis of the actions of prostaglandin on neuromuscular transmission in the guinea-pig vas deferens. J Physiol 29: 521-537.
27. 2. Br J Pharmacol, accompanying manuscript 162: 521-531.
28. 2-mimetic, the actions of which are slowly reversed by receptor blockade. Br J Pharmacol 96: 875-887.
29. Jones RL, Wise H, Clark R, Whiting RL, Bley KR, (2006). Investigation of the prostacyclin (IP) receptor antagonist RO1138452 on isolated blood vessel and platelet preparations. Br J Pharmacol 149: 110-120.
30. Jones RL, Giembycz MA, Woodward DF, (2009). Prostanoid receptor antagonists: development strategies and therapeutic applications. Br J Pharmacol 158: 104-145.
31. 3 receptors in the conscious rat. Br J Pharmacol 158: 372-381.
32. Kiriyama M, Ushikubi F, Kobayashi T, Hirata M, Sugimoto Y, Narumiya S, (1997). Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br J Pharmacol 122: 217-224.
33. Kirkpatrick P, (2003). Pressures in the pipeline. Nat Rev Drug Discov 2: 337.
34. Lawrence RA, Jones RL, Wilson NH, (1992). Characterization of receptors involved in the direct and indirect actions of prostaglandins E and I on the guinea-pig ileum. Br J Pharmacol 105: 271-278.
35. Lazareno S, Birdsall NJ, (1993). Estimation of competitive antagonist affinity from functional inhibition curves using the Gaddum, Schild and Cheng-Prusoff equations. Br J Pharmacol 109: 1110-1119.
36. Leff P, Dougall IG, (1993). Further concerns over Cheng-Prusoff analysis. Trends Pharmacol Sci 14: 110-112.
37. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ, (1997). Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Delivery Rev 23: 3-25.
38. Mannhold R, Poda GI, Ostermann C, Tetko IV, (2008). Calculation of molecular lipophilicity: state-of-the-art and comparison of log P methods on more than 96,000 compounds. J Pharm Sci 98: 861-893.
39. Matias I, Chen J, De Petrocellis L, Bisogno T, Ligresti A, Fezza F, et al. (2004). Prostaglandin ethanolamides (prostamides): in vitro pharmacology and metabolism. J Pharmacol Exp Ther 309: 745-757.
40. Matthews JS, Jones RL, (1993). Potentiation of aggregation and inhibition of adenylate cyclase in human platelets by prostaglandin E analogues. Br J Pharmacol 108: 363-369.
41. 2 receptor agonist. J Pharmacol Exp Ther 251: 557-562.
42. O'Connell M, Zeller W, Burgeson J, Mishra RK, Ramirez J, Kiselyov AS, et al. (2009). Peri-substituted hexahydro-indolones as novel, potent and selective human EP3 receptor antagonists. Bioorg Med Chem Lett 19: 778-782.
43. Okada Y, Hara A, Ma H, Xiao CY, Takahata O, Kohgo Y, et al. (2000). Characterization of prostanoid receptors mediating contraction of the gastric fundus and ileum: studies using mice deficient in prostanoid receptors. Br J Pharmacol 131: 745-755.
44. Perlmutter P, (1992). Conjugated Addition Reactions in Organic Synthesis. Pergamon: Oxford, p. 114.
45. Pratt WB, (1990). The entry, distribution and elimination of drugs. In:, Pratt WB, Taylor P, (eds). Principles of Drug Action, 3rd edn. Churchill-Livingstone: New York, pp. 201-296.
46. 3-receptor agonists on human isolated pulmonary artery. Br J Pharmacol 113: 369-374.
47. Rang HP, (1966). The kinetics of action of acetylcholine antagonists in smooth muscle. Proc Royal Soc Lond B 164: 488-510.
48. Roda A, Minutello A, Angellotti MA, Fini A, (1990). Bile acid structure-activity relationship: evaluation of bile acid lipophilicity using 1-octanol/water partition coefficient and reverse phase HPLC. J Lipid Res 31: 1433-1443.
49. Roden DM, (1999). Mechanisms underlying variability in response to drug therapy: implications for amiodarone use. Am J Cardiol 84: 29R-36R.
50. Saparov SM, Antonenko YN, Pohl P, (2006). A new model of weak acid permeation through membranes revisited: does Overton still rule? Biophys J 90: L86-L88.
51. Saussy DL, Goetz AS, King HK, True TA, (1994). BMY 7378 is a selective antagonist of α1D receptors. Can J Physiol Pharmacol 72: A323.
52. Schlemper V, Medeiros R, Ferreira J, Campos MM, Calixto JB, (2005). Mechanisms underlying the relaxation response induced by bradykinin in the epithelium-intact guinea-pig trachea in vitro. Br J Pharmacol 145: 740-750.
53. Senchyna M, Crankshaw DJ, (1996). Characterization of the prostanoid TP receptor population in human nonpregnant myometrium. J Pharmacol Exp Ther 279: 262-270.
54. 2/prostaglandin endoperoxide receptor in rabbit aorta. Regulation by dexamethasone. Circ Res 67: 1562-1569.
55. 3 receptor agonists. Br J Pharmacol 139: 1449-1461.
56. Smyth EM, Grosser T, Wang M, Yu Y, FitzGerald GA, (2009). Prostanoids in health and disease. J Lipid Res 50: S423-S428.
57. 2 receptor antagonist, [(3R)-4-(4-chloro-benzyl)-7-fluoro-5-(methylsulfonyl)-1,2, 3,4-tetrahydrocyclopenta[b] indol-3-yl]-acetic acid (MK-0524). J Med Chem 50: 794-806.
58. 4) in bone resorption: an analysis using specific agonists for the respective EPs. Endocrinology 141: 1554-1559.
59. Waldeck B, (1996). Some pharmacodynamic aspects on long-acting β-adrenoceptor agonists. Gen Pharmacol 27: 575-580.
60. Waring MJ, (2010). Lipophilicity in drug discovery. Expert Opin Drug Discovery 5: 235-248.
61. Wilson NH, Jones RL, Marr CG, Muir G, (1988). Synthesis of oxabicyclo[2.2.1]heptane prostanoids having thromboxane-like activity at subnanomolar concentrations. Eur J Med Chem 23: 359-364.
62. Woodward DF, Krauss AH, Chen J, Liang Y, Li C, Protzman CE, et al. (2003). Pharmacological characterization of a novel antiglaucoma agent, Bimatoprost (AGN 192024). J Pharmacol Exp Ther 305: 772-785.
63. Woodward DF, Krauss AH, Wang JW, Protzman CE, Nieves AL, Liang Y, et al. (2007). Identification of an antagonist that selectively blocks the activity of prostamides (prostaglandin-ethanolamides) in the feline iris. Br J Pharmacol 150: 342-352.
64. Young RN, Billot X, Han YX, Slipetz DA, Chauret N, Belley M, et al. (2004). Discovery and synthesis of a potent, selective and orally bioavailable EP4 receptor agonist. Heterocycles 64: 437-446.
65. 3 receptor antagonist, via tandem Heck reactions. Org Process Res Dev 11: 747-753.
66. 2/prostaglandin endoperoxide receptors in aorta. Eur J Pharmacol 317: 91-96.