Design of novel bicyclic analogues derived from a potent oxytocin antagonist

Journal of Peptide Science

Volumn 12, Issue 6, 2006, Pages 412-419

  Flouret, George ^a   Chaloin, Olivier ^a   Borovickova, Lenka ^b   Slaninová, Jirina ^b  

^a NORTHWESTERN UNIVERSITY   (United States)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

Antagonists; Bicyclic peptides; Oxytocin; Premature labor

Indexed keywords

AMIDE; ARGININE DERIVATIVE; ARGIPRESTOCIN; ASPARAGINE; ASPARTIC ACID DERIVATIVE; ATOSIBAN; DIAMINOBUTYRIC ACID; DIMER; GLYCINE; GLYCINE DERIVATIVE; LYSINE; NEUROHYPOPHYSIS HORMONE; ORNITHINE; OXYTOCIN ANTAGONIST; OXYTOCIN RECEPTOR; PEPTIDE; PROLINE DERIVATIVE; PROPIONIC ACID DERIVATIVE; UTEROTONIC AGENT;

ACYLATION; ARTICLE; ASSAY; CARBOXY TERMINAL SEQUENCE; CHEMICAL MODIFICATION; CYCLIZATION; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; NONHUMAN; PRIORITY JOURNAL;

AMINO ACID SEQUENCE; ANIMALS; BINDING, COMPETITIVE; CELL LINE; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; HORMONE ANTAGONISTS; HUMANS; MOLECULAR STRUCTURE; OLIGOPEPTIDES; OXYTOCIN; PEPTIDES, CYCLIC; RATS; RECEPTORS, OXYTOCIN; STRUCTURE-ACTIVITY RELATIONSHIP; UTERINE CONTRACTION; UTERUS;

EID: 33745326928     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.742     Document Type: Article

References (52)

1. Flouret G, Chaloin O, Slaninová J. Novel bicyclic analogues of a potent oxytocin antagonist. In Peptides 2002, Benedetti E, Pedone C (eds). Edizione Zino: Sorrento, 2003; 484-485.
2. Flouret G, Chaloin O, Slaninová J. Bicyclic analogues of a potent oxytocin antagonist. In Peptides 2004, Proceedings of the 3rd IPS and 28th EPS, Flegel M, Fridkin M, Gilon C, Slaninová J (eds). Prague, Sept. 2004.
3. Olah KS, Gee H. The prevention of preterm delivery-can we afford to continue to ignore the cervix? Br. J. Obstet. Gynaecol. 1992; 99: 278-280.
4. Creasy RK. Preterm birth prevention: Where we are? Am. J. Obstet. Gynecol. 1993; 168: 1223-1230.
5. Radetsky P. Stopping premature births before it is too late. Science 1995; 266: 1486-1488.
6. Chibbar R, Miller FD, Mitchell BF. Synthesis of oxytocin in amnion, chorion, and decidua may influence the timing of human parturition. J. Clin. Invest. 1993; 91: 185-192.
7. Norwitz ER, Robinson JM, Challis JRG. The control of labor. N. Engl. J. Med. 1999; 341: 660-666.
8. Challis JRG, Matthews SG, Gibb W, Lye SJ. Endocrine and paracrine regulation of birth at term and preterm. Endocr. Rev. 2000; 21: 514-550.
9. Weiss G. Endocrinology of parturition. J. Clin. Endocrinol. Metab. 2000; 85: 4421-4425.
10. Jard S. Vasopressin receptors. A historical survey. In Advances in Experimental Medicine and Biology, vol. 449, Vasopressin and Oxytocin, Zingg H, Bourque CW, Bichet DG (eds). Plenum Press: New York, 1998; 1-13.
11. Thibonnier M, Coles M, Thibonnier A, Shoham M. Molecular pharmacology and modeling of vasopressin receptors. In Progress in Brain Research, vol. 139, Poulain D, Oliet S, Theodosis D (eds). Elsevier Science: Amsterdam, 2002; 179-196, Chapt. 14.
12. Gimpl G, Fahrenholz F. The oxytocin receptor system, structure, function and regulation. Physiol. Rev. 2001; 81: 629-683.
13. Leveno KJ, Cunningham FG. β-Adrenergic agonists for preterm labor. N. Engl. J. Med. 1992; 327: 349-351.
14. Hruby VJ, Smith CW. Structure-activity relationships of neurohypophyseal peptides. In The Peptides, Udenfriend S, Meienhofer J (eds). vol. 8, Chemistry, Biology and Medicine of Neurohypophyseal Hormones and their Analogs, Smith CW (ed.). Academic Press: Orlando, FL, 1987; 77-207.
15. Manning M, Cheng LL, Klis WA, Stoev SA, Przybylski J, Bankowski K, Sawyer WH, Barberis C, Chan WY. Advances in the design of selective antagonists, potential tocolytics and radioiodinated ligands for oxytocin receptors. In Oxytocin: Cellular and Molecular Approaches in Medicine and Research, Ivell R, Russell J (eds). Plenum Press: New York, 1995; 559-583.
16. Goodwin TM, Zograbyan A. Oxytocin receptor antagonists update. Clin. Perinatol. 1998; 25: 859-871.
17. Manning M, Stoev S, Cheng LL, Wo NC, Chan WY. Design of oxytocin antagonists, which are more selective than Atosiban. J. Peptide Sci. 2001; 7: 449-465.
18. Flouret G, Chaloin O, Slaninová J. Antagonists of oxytocin featuring replacement with modified β-mercaptopropionic acids at position 1. J. Peptide Sci. 2002; 8: 314-326.
19. Flouret G, Chaloin O, Slaninová J. Analogues of a potent oxytocin antagonist with truncated C-terminus or shorter amino acid side chain of the basic amino acid at position 8. J. Peptide Sci. 2003; 9: 393-401.
20. Freidinger RM, Bock MG, Evans BE, Pettibone DJ, Williams PD. Design of novel, nonpeptide oxytocin receptor antagonists. In Peptide Science - Present and Future, Shimonishi Y (ed.). Kluwer Academic: Dordrecht, 1999; 618-622.
21. Melin P, Trojnar J, Johanson B, Vilhardt H, Åkerlund M. Synthetic antagonists of the myometrial response to vasopressin and oxytocin. J. Endocrinol. 1986; 111: 125-131.
22. Åkerlund M, Stromberg P, Hauksson A, Andersen LF, Lyndrup J, Trojnar J, Melin P. Inhibition of uterine contractions of premature labour with an oxytocin analogue. Br. J. Obstet. Gynaecol. 1987; 94: 1040-1044.
23. Romero R, Sibai BM, Sanchez-Ramos L, Valenzuela GJ, Veille J-C, Tabor B, Perry KG, Varner M, Goddwin TM, Lane R, Smith J, Shangold G, Creasy GW. An oxytocin receptor antagonist (Atosiban) in the treatment of preterm labor: a randomized, double-blind, placebo-controlled trial with tocolytic rescue. Am. J. Obstet. Gynecol. 2000; 182: 1173-1183.
24. New drug for delaying premature birth marketed. Pharm. J. 2000; 264: 871.
25. Flouret G, Brieher W, Mahan K, Wilson L Jr. Design of potent oxytocin antagonists featuring D-tryptophan at position 2. J. Med. Chem. 1991; 34: 642-646.
26. Wilson L Jr, Parsons MT, Ouano L, Flouret G. A new tocolytic agent: development of an oxytocin antagonist for inhibiting uterine contractions. Am. J. Obstet. Gynecol. 1990; 163: 195-202.
27. Wilson L Jr, Parsons MT, Flouret G. Inhibition of spontaneous uterine contractions during the last trimester in pregnant baboons by an oxytocin antagonist. Am. J. Obstet. Gynecol. 1990; 163: 1875-1882.
28. Flouret G, Brieher W, Majewski T, Mahan K, Wilson L Jr. Improvement in potency of an oxytocin antagonist after systematic substitutions with L-tryptophan. J. Med. Chem. 1991; 34: 2089-2094.
29. Flouret G, Brieher W, Majewski T, Wilson L Jr. Some pharmacological properties of cyclic and linear analogs obtained by substituting each residue of an oxytocin antagonist with D-tryptophan. Int. J. Pept. Protein Res. 1991; 38: 169-175.
30. Hruby VJ, Chow MS, Smith DD. Conformational and structural considerations in oxytocin receptor binding and biological activity. Annu. Rev. Pharmacol. Toxicol. 1990; 30: 501-534.
31. Smith DD, Slaninová J, Hruby VJ. Structure-activity studies of a novel bicyclic oxytocin antagonist. J. Med. Chem. 1992; 35: 1558-1563.
32. Holton P. A modification of the method of dale and Laidlaw for standardization of posterior pituitary extract. Br. J. Pharmacol. 1948; 3: 328-334.
33. Merrifield RB. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 1963; 85: 2149-2154.
34. Stewart JM, Young JD. Solid Phase Peptide Synthesis, 2nd edn. Pierce Chemical: Rockford, IL, 1984; 1-176.
35. Gisin BF. Preparation of Merrifield resins through total esterification with cesium salts. Helv. Chim. Acta 1973; 56: 1476-1482.
36. Kaiser E, Colescot RL, Bossinger CD, Cook PI. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 1970; 34: 595-598.
37. Manning M. Synthesis by the Merrifield method of a protected nonapeptide amide with the amino acid sequence of oxytocin. J. Am. Chem. Soc. 1968; 90: 1348-1349.
38. du Vigneaud V, Ressler C, Swan JM, Roberts CW, Katsoyannis PG, Gordon S. The synthesis of an octapeptide amide with the hormonal activity of oxytocin. J. Am. Chem. Soc. 1953; 75: 4879-4880.
39. Sakakibara S, Shimonishi Y. A new method for releasing oxytocin from fully protected nonapeptides using anhydrous hydrogen fluoride. Bull. Chem. Soc. Jpn. 1965; 38: 1412-1413.
40. Manning M, Lammek B, Kolodziejczyk AM. Synthetic antagonists of in vivo antidiuretic and vasopressor responses to arginine-vasopressin. J. Med. Chem. 1981; 24: 701-706.
41. Hope DB, Murti VVS, du Vigneaud V. A highly potent analogue of oxytocin, desamino-oxytocin. J. Biol. Chem. 1962; 237: 1563-1566.
42. Bidlingmeyer BA, Cohen SA, Tarvin TL. Rapid Analysis of amino acids using pre-column derivatization. J. Chromatogr. 1984; 336: 93-104.
43. Munsick RA. Effect of magnesium ion on the response of the rat uterus to neurohypophysial hormones and analogues. Endocrinology 1960; 66: 451-457.
44. Schild HO. pA, a new scale for the measurement of drug antagonism. Br. J. Pharmacol. 1947; 2: 189-206.
45. Vávra I, Machová A, Krejci I. Antidiuretic action of 1-deamino-8-D-arginine vasopressin in unanesthetized rats. J. Pharmacol. Exp. Ther. 1974; 188: 241-247.
46. Hrbas P, Barth T, Skopkova J, Lebl M, Jost K. Effect of some oxytocin analogues on natriuresis in rats. Endocrinol. Exp. 1980; 14: 151-157.
47. Dekanski J. The quantitative assay of vasopressin. Br. J. Pharmacol. 1952; 7: 567-572.
48. Slaninová J. Fundamental Biological Evaluation. In Handbook of Neurohypophyseal Hormone Analogues, vol. 1, Part 2, Jost K, Lebl M, Brtnik F (eds.) CRC Press: Boca Raton, FL, 1987; 83-107.
49. Gimpl G, Burger K, Fahrenholz F. Cholesterol as modulator of receptor function. Biochemistry 1997; 36: 10 959-10 974.
50. Fahrenholz F, Boer R, Crause P, Fritzsch G, Grzonka Z. Interactions of vasopressin agonists and antagonists with membrane receptors. Eur. J. Pharmacol. 1984; 100: 47-58.
51. Fahrenholz F, Hackenberg M, Muller M. Identification of a myometrial oxytocin receptor protein. Eur. J. Biochem. 1988; 174: 81-85.
52. Soloff MS, Swartz TL. Characterization of a proposed oxytocin receptor in the uterus of the rat and sow. J. Biol. Chem. 1974; 249: 1376-1381.