New, potent, selective, and short-acting peptidic V1a receptor agonists

Journal of Medicinal Chemistry

Volumn 54, Issue 13, 2011, Pages 4388-4398

  Wiśniewski, Kazimierz ^a   Galyean, Robert ^a   Tariga, Hiroe ^a   Alagarsamy, Sudarkodi ^a   Croston, Glenn ^a   Heitzmann, Joshua ^a   Kohan, Arash ^a   Wiśniewska, Halina ^a   Laporte, Régent ^a   Rivière, Pierre J M ^a   Schteingart, Claudio D ^a  

^a Ferring Pharmaceuticals AS   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

FE 202158; HORMONE RECEPTOR STIMULATING AGENT; UNCLASSIFIED DRUG; VASOPRESSIN V1A RECEPTOR;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG MECHANISM; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; MALE; NONHUMAN; RAT;

ANIMALS; BLOOD PRESSURE; HEK293 CELLS; HUMANS; MALE; OLIGOPEPTIDES; RATS; RATS, WISTAR; RECEPTORS, VASOPRESSIN; STRUCTURE-ACTIVITY RELATIONSHIP; VASOPRESSINS;

EID: 79960171889     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200278m     Document Type: Article

References (54)

1. Barberis, C.; Mouillac, B.; Durroux, T. Structural Bases of Vasopressin/Oxytocin Receptor Function J. Endocrinol. 1998, 156, 223-229 (Pubitemid 28105809)
2. Caldwell, H. K.; Young, W. S., III. Oxytocin and Vasopressin: Genetics and Behavioral Implications. In Handbook of Neurochemistry and Molecular Neurobiology: Neuroactive Proteins and Peptides (3rd ed.; Lim, R.; Lajtha, A., Eds.; Springer: New York, 2006; pp 573-607.
3. Jard, S. Vasopressin Receptors: A Historical Survey Adv. Exp. Med. Biol. 1998, 449, 1-13 (Pubitemid 128699397)
4. Ring, R. H. The Central Vasopressinergic System: Examining the Opportunities for Psychiatric Drug Development Curr. Pharm. Des. 2005, 11, 205-225 (Pubitemid 40089841)
5. 1b Receptors: A Combined Pharmacological/Knockout Approach Mol. Pharmacol. 2004, 65, 623-629 (Pubitemid 38264029)
6. 1a Vasopressin Receptors Gen. Pharmacol. 1995, 26, 1143-1152
7. Oliver, J. A.; Landry, D. W. Endogenous and Exogenous Vasopressin in Shock Curr. Opin. Crit. Care 2007, 13, 376-382 (Pubitemid 47015773)
8. Landry, D. W.; Levin, H. R.; Gallant, E. M.; Ashton, R. C., Jr.; Seo, S.; D'Alessandro, D.; Oz, M. C.; Oliver, J. A. Vasopressin Deficiency Contributes to the Vasodilation of Septic Shock Circulation 1997, 95, 1122-1125 (Pubitemid 27097820)
9. Holmes, C. L.; Walley, K. R. Arginine Vasopressin in the Treatment of Vasodilatory Septic Shock Best Pract. Res. Clin. Anaesthesiol. 2008, 22, 275-286 (Pubitemid 351824568)
10. Russell, J. A.; Walley, K. R.; Singer, J.; Gordon, A. C.; Hebert, P. C.; Cooper, D. J.; Holmes, C. L.; Mehta, S.; Granton, J. T.; Storms, M. M.; Cook, D. J.; Presneill, J. J.; Ayers, D. Vasopressin Versus Norepinephrine Infusion in Patients with Septic Shock N. Engl. J. Med. 2008, 358, 877-887 (Pubitemid 351397087)
11. Halimi, C.; Bonnard, P.; Bernard, B.; Mathurin, P.; Mofredj, A.; di Martino, V.; Demontis, R.; Henry-Biabaud, E.; Fievet, P.; Opolon, P.; Poynard, T.; Cadranel, J. F. Effect of Terlipressin (Glypressin) on Hepatorenal Syndrome in Cirrhotic Patients: Results of a Multicentre Pilot Study Eur. J. Gastroenterol. Hepatol. 2002, 14, 153-158 (Pubitemid 34163994)
12. O'Brien, A.; Clapp, L.; Singer, M. Terlipressin for Norepinephrine- Resistant Septic Shock Lancet 2002, 359, 1209-1210 (Pubitemid 34304264)
13. Delmas, A.; Leone, M.; Rousseau, S.; Albanese, J.; Martin, C. Clinical Review: Vasopressin and Terlipressin in Septic Shock Patients Crit. Care 2005, 9, 212-222 (Pubitemid 40425448)
14. Pesaturo, A. B.; Jennings, H. R.; Voils, S. A. Terlipressin: Vasopressin Analog and Novel Drug for Septic Shock Ann. Pharmacother. 2006, 40, 2170-2177 (Pubitemid 44954436)
15. Kaufmann, J. E.; Vischer, U. M. Cellular Mechanisms of the Hemostatic Effects of Desmopressin (DDAVP) J. Thromb. Haemost. 2003, 1, 682-689
16. Wiśniewski, K.; Alagarsamy, S.; Taki, H.; Miampamba, M.; Laporte, R.; Gaylean, R.; Croston, G.; Schteingart, C. D.; Riviere, P. J.-M.; Trojnar, J. Synthesis and Biological Activity of Terlipressin and Its Putative Metabolites. In Understanding Biology Using Peptides, Proceedings of the19th American Peptide Symposium; Blondelle, S. E., Ed.; Springer: New York, 2005; pp 489-490.
17. Freidinger, R. M.; Pettibone, D. J. Small Molecule Ligands for Oxytocin and Vasopressin Receptors Med. Res. Rev. 1997, 17, 1-16 (Pubitemid 27037480)
18. 1b Receptor Ligands Prog. Brain Res. 2002, 139, 197-210 (Pubitemid 35460890)
19. du Vigneaud, V.; Gish, D. T.; Katsoyannis, P. G. Synthetic Preparation Possessing Biological Properties Associated with Arginine Vasopressin J. Am. Chem. Soc. 1954, 76, 4751-4752
20. Manning, M.; Przybylski, J. P.; Olma, A.; Klis, W. A.; Kruszynski, M.; Wo, N. C.; Pelton, G. H.; Sawyer, W. H. No Requirement of Cyclic Conformation of Antagonists in Binding to Vasopressin Receptors Nature (London) 1987, 329, 839-840 (Pubitemid 17152212)
21. 2 Agonists: Potential Radioiodinated Ligands for Vasopressin Receptors. In Peptides 1990, Proceedings of the 21st European Peptide Symposium; Giralt, E.; Andreu, D., Eds.; ESCOM, Leiden, The Netherlands, 1991; pp 665-667.
22. 8-Oxytocin, Two Analogs of Vasopressin with Selective Pressor Activity Helv. Chim. Acta 1964, 47, 1934-1941
23. Aurell, C. J.; Bengtsson, B.; Ekholm, K.; Kasprzykowska, R.; Nilsson, A.; Persson, R.; Trojnar, J.; Abbe, M.; Melin, P. Development of Vasopressor Specific Vasotocin Analogs with Prolonged Effects. In Peptides 1990, Proceedings of the 21st European Peptide Symposium; Giralt, E.; Andreu, D., Eds.; ESCOM, Leiden, The Netherlands, 1991; pp 671-673.
24. 1a Vasopressin Receptor Agonist of High Affinity Br. J. Pharmacol. 2002, 135, 1828-1836 (Pubitemid 36132714)
25. Favre, N.; Fanelli, F.; Missotten, M.; Nichols, A.; Wilson, J.; di Tiani, M.; Rommel, C.; Scheer, A. The Dry Motif as a Molecular Switch of the Human Oxytocin Receptor Biochemistry 2005, 44, 9990-10008 (Pubitemid 41076795)
26. Wootten, D. L.; Simms, J.; Massoura, A. J.; Trim, J. E.; Wheatley, M. Agonist-Specific Requirement for a Glutamate in Transmembrane Helix 1 of the Oxytocin Receptor Mol. Cell. Endocrinol. 2011, 333, 20-27
27. 2-Arginine-Vasotocin and New Syntheses of Arginine-Vasopressin and Arginine-Vasotocin Helv. Chim. Acta 1962, 45, 1629-1643
28. 8-Oxytocin Helv. Chim. Acta 1963, 46, 1669-1676
29. Zaoral, M.; Kolc, J.; Sorm, F. Amino Acids and Peptides. LXXI. Synthesis of 1-Deamino-8- d -G-Aminobutyrine Vasopressin, 1-Deamino-8- d -Lysine Vasopressin, and 1-Deamino-8- d -Arginine Vasopressin Collect. Czech. Chem. Commun. 1967, 32, 1250-1257
30. 1b Vasopressin Receptor Biochem. Pharmacol. 1997, 53, 1711-1717 (Pubitemid 27356101)
31. Barlos, K.; Gatos, D.; Chatzi, O.; Koutsogianni, S.; Schaefer, W. Solid Phase Synthesis Using Trityl Type Side Chain Protecting Groups. In Peptides 1992, Proceedings of the 22nd European Peptide Symposium; Schneider, C. H.; Eberle, A. N., Eds.; ESCOM, Leiden, The Netherlands, 1993; pp 283-284.
32. Fukuyama, T.; Jow, C.-K.; Cheung, M. 2- and 4-Nitrobenzenesulfonamides: Exceptionally Versatile Means for Preparation of Secondary Amines and Protection of Amines Tetrahedron Lett. 1995, 36, 6373-6374
33. Mitsunobu, O. The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products Synthesis 1981, 1-28
34. α-Boc- l -Glutamic Acid Int. J. Pept. Protein Res. 1990, 35, 215-218 (Pubitemid 20126876)
35. Bolin, D. R.; Wang, C. T.; Felix, A. M. Preparation of N-tert -Butyloxycarbonyl- O -ω-9-Fluorenylmethyl Esters of Aspartic and Glutamic Acids Org. Prep. Proced. Int. 1989, 21, 67-74
36. Konieczna, E.; Czaja, M.; Kasprzykowska, R.; Kozlowski, A.; Dziecioł, K.; Trzeciak, H. I.; Lammek, B. Synthesis and Biological Activity of Arginine-Vasopressin Analogs Modified with l -Alanine or L -Proline Pol. J. Chem. 1994, 68, 1535-1543
37. Jastrzebska, B.; Derdowska, I.; Kowalczyk, W.; Machova, A.; Slaninova, J.; Lammek, B. Influence of 1-Aminocyclohexane-1-Carboxylic Acid in Position 2 or 3 of AVP and Its Analogues on Their Pharmacological Properties J. Pept. Res. 2003, 62, 70-77 (Pubitemid 36819304)
38. Kowalczyk, W.; Prahl, A.; Dawidowska, O.; Derdowska, I.; Sobolewski, D.; Hartrodt, B.; Neubert, K.; Slaninova, J.; Lammek, B. The Influence of 1-Aminocyclopentane-1-Carboxylic Acid at Position 2 or 3 of AVP and Its Analogues on Their Pharmacological Properties J. Pept. Sci. 2005, 11, 584-588 (Pubitemid 41195249)
39. 2 Agonists of Arginine Vasopressin J. Med. Chem. 2004, 47, 6020-6024 (Pubitemid 39507343)
40. Kruszynski, M.; Manning, M.; Wo, N. C.; Sawyer, W. H. Invertebrate Neuropeptides Resembling Vasotocin and Some Analogs: Synthesis and Pharmacological Properties Experientia 1990, 46, 771-773 (Pubitemid 20216661)
41. Sawyer, W. H.; Acosta, M.; Balaspiri, L.; Judd, J.; Manning, M. Structural Changes in Arginine Vasopressin Molecule That Enhance Antidiuretic Activity and Specificity Endocrinology 1974, 9, 1106-1115
42. 1]Arginine Vasopressin at Position 4 J. Med. Chem. 2004, 47, 2375-2388 (Pubitemid 38478861)
43. 1b Receptor Selectivity J. Pept. Sci. 2006, 12, 190-198 (Pubitemid 43349359)
44. 1b- Selective Agonist for Rat Vasopressin/Oxytocin Receptors Endocrinology 2007, 148, 4136-4146 (Pubitemid 47295698)
45. 1]Arginine Vasopressin at Positions 4 and 8 J. Med. Chem. 2007, 50, 835-847 (Pubitemid 46332995)
46. 1a Receptor Full Agonist for the Treatment of Vasodilatory Hypotension J. Pharmacol. Exp. Ther. 2011, 337, 786-796
47. Lovgren, U.; Johansson, S.; Jensen, L. S.; Ekstrom, C.; Carlshaf, A. Quantitative Determination of Peptide Drug in Human Plasma Samples at Low pg/mL Levels Using Coupled Column Liquid Chromatography-Tandem Mass Spectrometry J. Pharm. Biomed. Anal. 2010, 53, 537-545
48. Wiśniewski, K.; Kołodziejczyk, A. S. The Efficient Synthesis of Fmoc- l -Homoglutamine Org. Prep. Proced. Int. 1997, 29, 338-340
49. Hoeger, C.; Galyean, R.; Boublik, J.; McClintock, R.; Rivier, J. Preparative Reversed Phase High Performance Liquid Chromatography: Effects of Buffer pH on the Purification of Synthetic Peptides BioChromatography 1987, 2, 134-142
50. Boss, V.; Talpade, D. J.; Murphy, T. J. Induction of NFAT-Mediated Transcription by Gq-Coupled Receptors in Lymphoid and Non-Lymphoid Cells J. Biol. Chem. 1996, 271, 10429-10432
51. Fitzgerald, L. R.; Mannan, I. J.; Dytko, G. M.; Wu, H. L.; Nambi, P. Measurement of Responses from Gi-, Gs-, or Gq-Coupled Receptors by a Multiple Response Element/Camp Response Element-Directed Reporter Assay Anal. Biochem. 1999, 275, 54-61
52. Dekanski, J. The Quantitative Assay of Vasopressin Br. J. Pharmacol. Chemother. 1952, 7, 507-572
53. Erker, E. F.; Chan, W. Y. The Site and the Mechanism of Phenoxy-Benzamine Potentiation of the Pressor Response to Oxytocin and Vasopressin: In Vivo and Isolated Aortic Strips Studies J. Pharmacol. Exp. Ther. 1977, 202, 287-293 (Pubitemid 8168191)
54. Hoffman, W. E. Regional Vascular Effects of Antidiuretic Hormone in Normal and Sympathetic Blocked Rats Endocrinology 1980, 107, 334-341 (Pubitemid 10080429)