Targeting the prostaglandin f2α receptor for preventing preterm labor with azapeptide tocolytics

Journal of Medicinal Chemistry

Volumn 54, Issue 17, 2011, Pages 6085-6097

  Bourguet, Carine B ^c   Goupil, Eugénie ^a,b   Tassy, Danaë ^c   Hou, Xin ^d   Thouin, Eryk ^c   Polyak, Felix ^c   Hébert, Terence E ^b   Claing, Audrey ^c   Laporte, Stéphane A ^a,b   Chemtob, Sylvain ^b,d   Lubell, William D ^c  

^a RESEARCH INSTITUTE OF THE MCGILL UNIVERSITY HEALTH CENTRE   (Canada)

^b MCGILL UNIVERSITY   (Canada)

^c UNIVERSITÉ DE MONTRÉAL   (Canada)

^d CENTRE HOSPITALIER DE L UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; CYCLOALKANE DERIVATIVE; INDOLIZIDINE DERIVATIVE; MITOGEN ACTIVATED PROTEIN KINASE 1; PEPTIDE DERIVATIVE; PROSTAGLANDIN F2 ALPHA; PROSTAGLANDIN RECEPTOR; UTERUS SPASMOLYTIC AGENT;

ALLOSTERISM; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; MOUSE; NONHUMAN; PREMATURE LABOR; SIGNAL TRANSDUCTION; STEREOCHEMISTRY;

ANIMALS; AZA COMPOUNDS; BLOTTING, WESTERN; CELLS, CULTURED; DINOPROST; EXTRACELLULAR SIGNAL-REGULATED MAP KINASES; FEMALE; HUMANS; INFANT, NEWBORN; KIDNEY; MICE; OBSTETRIC LABOR, PREMATURE; PEPTIDE FRAGMENTS; PREGNANCY; PREGNANCY, ANIMAL; RECEPTORS, PROSTAGLANDIN; RHO-ASSOCIATED KINASES; SIGNAL TRANSDUCTION; TOCOLYTIC AGENTS; UTERINE CONTRACTION;

EID: 80052357124     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200608k     Document Type: Article

References (51)

1. Goupil; et al. J. Biol. Chem. 2010, 285, 25624 - 25636
2. Slattery, M. M.; Morrison, J. J. Preterm delivery Lancet 2002, 360, 1489-1497 (Pubitemid 35356329)
3. Goldenberg, R. L.; Culhane, J. F.; Iams, J. D.; Romero, R. Preterm birth 1: epidemiology and causes of preterm birth Lancet 2008, 371, 75-84
4. Martin, J. A.; Kochanek, K. D.; Strobino, D. M.; Guyer, B.; MacDorman, M. F. Annual summary of vital statistics: 2003 Pediatrics 2005, 115, 619-634 (Pubitemid 43373022)
5. Russell, R. B.; Green, N. S.; Steiner, C. A.; Meikle, S.; Howse, J. L.; Poschman, K.; Dias, T.; Potetz, L.; Davidoff, M. J.; Damus, K.; Petrini, J. R. Cost of hospitalization for preterm and low birth weight infants in the United States Pediatrics 2007, 120, E1-E9
6. McCormick, M. C. The contribution of low birth-weight to infant-mortality and childhood morbidity N. Engl. J. Med. 1985, 312, 82-90 (Pubitemid 15192138)
7. Hack, M.; Flannery, D. J.; Schluchter, M.; Cartar, L.; Borawski, E.; Klein, N. Outcomes in young adulthood for very-low-birth-weight infants N. Engl. J. Med. 2002, 346, 149-157 (Pubitemid 34438880)
8. Robertson, P. A.; Sniderman, S. H.; Laros, R. K.; Cowan, R.; Heilbron, D.; Goldenberg, R. L.; Iams, J. D.; Creasy, R. K. Neonatal morbidity according to gestational-age and birth-weight from 5 tertiary care centers in the United-States, 1983 through 1986 Am. J. Obstet. Gynecol. 1992, 166, 1629-1645
9. RichEdwards, J. W.; Stampfer, M. J.; Manson, J. E.; Rosner, B.; Hankinson, S. E.; Colditz, G. A.; Willett, W. C.; Hennekens, C. H. Birth weight and risk of cardiovascular disease in a cohort of women followed up since 1976 Br. Med. J. 1997, 315, 396-400 (Pubitemid 27346039)
10. Iams, J. D.; Romero, R.; Culhane, J. F.; Goldenberg, R. L. Preterm birth 2: primary, secondary, and tertiary interventions to reduce the morbidity and mortality of preterm birth Lancet 2008, 371, 164-175
11. Anotayanonth, S.; Subhedar, N. V.; Garner, P.; Neilson, J. P.; Harigopal, S. Betamimetics for inhibiting preterm labour Cochrane Database Syst. Rev. 2004, CD004352
12. Mittendorf, R.; Covert, R.; Boman, J.; Khoshnood, B.; Lee, K. S.; Siegler, M. Is tocolytic magnesium sulphate associated with increased total paediatric mortality? Lancet 1997, 350, 1517-1518 (Pubitemid 28036557)
13. Papatsonis, D.; Flenady, V.; Cole, S.; Liley, H. Oxytocin receptor antagonists for inhibiting preterm labour Cochrane Database Syst. Rev. 2005, CD004452
14. Goodwin, T. M.; Valenzuela, G.; Silver, H.; Hayashi, R.; Creasy, G. W.; Lane, R. Treatment of preterm labor with the oxytocin antagonist atosiban Am. J. Perinatol. 1996, 13, 143-146 (Pubitemid 26099267)
15. Duchateau, F. X.; Max, A.; Harscoat, S.; Curac, S.; Ricard-Hibon, A.; Mantz, J. Comparison between atosiban and nicardipine in inducing hypotension during in-utero transfers for threatening premature delivery Eur. J. Emerg. Med. 2010, 17, 142-145
16. King, J. F.; Flenady, V.; Papatsonis, D.; Dekker, G.; Carbonne, B. Calcium channel blockers for inhibiting preterm labour; a systematic review of the evidence and a protocol for administration of nifedipine Aust. N. Z. J. Obstet. Gynaecol. 2003, 43, 192-198 (Pubitemid 36790188)
17. Coomarasamy, A.; Knox, E. M.; Gee, H.; Song, F. J.; Khan, K. S. Effectiveness of nifedipine versus atosiban for tocolysis in preterm labour: a meta-analysis with an indirect comparison of randomised trials BJOG 2003, 110, 1045-1049 (Pubitemid 37510145)
18. Higby, K.; Xenakis, E. M. J.; Pauerstein, C. J.; Harbert, G. M.; Jones, H.; Merkatz, I. R.; Creasy; Woods, J.; Cefalo, R. C.; Gibbs, R. S.; Scott, S.; Queenan, J. T.; Kirschbaum; Nelson, K. Do tocolytic agents stop preterm labor: a critical and comprehensive review of efficacy and safety Am. J. Obstet. Gynecol. 1993, 168, 1247-1259 (Pubitemid 23122176)
19. Haas, D. M.; Imperiale, T. F.; Kirkpatrick, P. R.; Klein, R. W.; Zollinger, T. W.; Golichowski, A. M. Tocolytic Therapy: a meta-analysis and decision analysis Obstet. Gynecol. 2009, 113, 585-594
20. Marshall, C. The art of induction/augmentation of labor J. Obstet. Gynecol. Neonat. Nurs. 1985, 14, 22-8
21. Olson, D. M. The role of prostaglandins in the initiation of parturition Best Pract. Res., Clin. Obstet. Gynaecol. 2003, 17, 717-730 (Pubitemid 37168291)
22. Brodt-Eppley, J.; Myatt, L. Prostaglandin receptors in lower segment myometrium during gestation and labor Obstet. Gynecol. 1999, 93, 89-93
23. Sugimoto, Y.; Segi, E.; Tsuboi, K.; Ichikawa, A.; Narumiya, S. Female Reproduction in Mice Lacking the Prostaglandin F Receptor. Roles of Prostaglandin and Oxytocin Receptors in Parturition. In Vasopressin and Oxytocin: Molecular, Cellular, and Clinical Advances; Zingg, H. H.; Bourque, C. W.; Bichet, D. G., Eds.; Plenum Press: New York, 1998; Vol. 449, pp 317-321.
24. Sugimoto, Y.; Yamasaki, A.; Segi, E.; Tsuboi, K.; Aze, Y.; Nishimura, T.; Oida, H.; Yoshida, N.; Tanaka, T.; Katsuyama, M.; Hasumoto, K.; Murata, T.; Hirata, M.; Ushikubi, F.; Negishi, M.; Ichikawa, A.; Narumiya, S. Failure of parturition in mice lacking the prostaglandin F receptor Science 1997, 277, 681-683 (Pubitemid 27373912)
25. Goupil, E.; Tassy, D.; Bourguet, C.; Quiniou, C.; Wisehart, V.; Petrin, D.; Le Gouill, C.; Devost, D.; Zingg, H. H.; Bouvier, M.; Saragovi, H. U.; Chemtob, S.; Lubell, W. D.; Claing, A.; Hebert, T. E.; Laporte, S. A. A novel biased allosteric compound inhibitor of parturition selectively impedes the prostaglandin F2 alpha-mediated Rho/ROCK signaling pathway J. Biol. Chem. 2010, 285, 25624-25636
26. Presland, J. Identifying novel modulators of G protein-coupled receptors via interaction at allosteric sites Curr. Opin. Drug Discovery Dev. 2005, 8, 567-576 (Pubitemid 41224119)
27. Kenakin, T. P. Ligand detection in the allosteric world J. Biomol. Screening 2010, 15, 119-130
28. Peri, K. G.; Quiniou, C.; Hou, X.; Abran, D.; Varma, D. R.; Lubell, W. D.; Chemtob, S. THG113: a novel selective FP antagonist that delays preterm labor Semin. Perinatol. 2002, 26, 389-397 (Pubitemid 36133536)
29. Peri, K.; Polyak, F.; Lubell, W.; Thouin, E.; Chemtob, S. Peptides and Peptidomimetics Useful for Inhibiting the Avtivity of Prostaglandin F2α Receptor. WO/2003/104266, 2003.
30. Hirst, J. J.; Parkington, H. C.; Young, I. R.; Palliser, H. K.; Peri, K. G.; Olson, D. M. Delay of preterm birth in sheep by THG113.31, a prostaglandin F2 alpha receptor antagonist Am. J. Obstet. Gynecol. 2005, 193, 256-266 (Pubitemid 40991854)
31. Hummel, G.; Reineke, U.; Reimer, U. Translating peptides into small molecules Mol. BioSyst. 2006, 2, 499-508 (Pubitemid 44433808)
32. Vlieghe, P.; Lisowski, V.; Martinez, J.; Khrestchatisky, M. Synthetic therapeutic peptides: science and market Drug Discovery Today 2010, 15, 40-56
33. Edwards, C. M. B.; Cohen, M. A.; Bloom, S. R. Peptides as drugs QJM 1999, 92, 1-4 (Pubitemid 29034093)
34. Lombart, H. G.; Lubell, W. D. Rigid dipeptide mimetics: efficient synthesis of enantiopure indolizidinone amino acids J. Org. Chem. 1996, 61, 9437-9446 (Pubitemid 27067106)
35. Halab, L.; Becker, J. A. J.; Darula, Z.; Tourwe, D.; Kieffer, B. L.; Simonin, F.; Lubell, W. D. Probing opioid receptor interactions with azacycloalkane amino acids. Synthesis of a potent and selective ORL1 antagonist J. Med. Chem. 2002, 45, 5353-5357 (Pubitemid 35429174)
36. Polyak, F.; Lubell, W. D. Rigid dipeptide mimics: synthesis of enantiopure 5- and 7-benzyl and 5,7-dibenzyl indolizidinone amino acids via enolization and alkylation of delta-oxo alpha,omega-di- N -(9-(9- phenylfluorenyl))amino azelate esters J. Org. Chem. 1998, 63, 5937-5949 (Pubitemid 128491759)
37. Gosselin, F.; Lubell, W. D. Rigid dipeptide surrogates: syntheses of enantiopure quinolizidinone and pyrroloazepinone amino acids from a common diaminodicarboxylate precursor J. Org. Chem. 2000, 65, 2163-2171 (Pubitemid 30193903)
38. Gosselin, F.; Lubell, W. D. An olefination entry for the synthesis of enantiopure alpha,omega-diaminodicarboxylates and azabicyclo X.Y.0 alkane amino acids J. Org. Chem. 1998, 63, 7463-7471 (Pubitemid 128722978)
39. Degrado, W. F.; Kaiser, E. T. Polymer-bound oxime esters as supports for solid-phase peptide synthesis. Preparation of protected peptide-fragments J. Org. Chem. 1980, 45, 1295-1300
40. Kaiser, E. T.; Mihara, H.; Laforet, G. A.; Kelly, J. W.; Walters, L.; Findeis, M. A.; Sasaki, T. Peptide and protein synthesis by segment synthesis-condensation Science 1989, 243, 187-192 (Pubitemid 19035351)
41. Andre, F.; Boussard, G.; Bayeul, D.; Didierjean, C.; Aubry, A.; Marraud, M. Aza-peptides. 2. X-ray structures of aza-alanine and aza-asparagine- containing peptides J. Pept. Res. 1997, 49, 556-562 (Pubitemid 27335000)
42. Reviewed in the following: Proulx, C.; Sabatino, D.; Hopewell, R.; Spiegel, J.; García-Ramos, Y.; Lubell, W. D. Azapeptides and their therapeutic potential: current issues and new possibilities Future Med. Chem. 2011, 3, 1139-1164
43. Lee, H. J.; Choi, K. H.; Ahn, I. A.; Ro, S.; Jang, H. G.; Choi, Y. S.; Lee, K. B. The beta-turn preferential solution conformation of a tetrapeptide containing an azaamino acid residue J. Mol. Struct. 2001, 569, 43-54 (Pubitemid 32660721)
44. Thormann, M.; Hofmann, H. J. Conformational properties of azapeptides J. Mol. Struct.: THEOCHEM 1999, 469, 63-76
45. Boeglin, D.; Hamdan, F. F.; Melendez, R. E.; Cluzeau, J.; Laperriere, A.; Heroux, M.; Bouvier, M.; Lubell, W. D. Calcitonin gene-related peptide analogues with aza and indolizidinone amino acid residues reveal conformational requirements for antagonist activity at the human calcitonin gene-related peptide 1 receptor J. Med. Chem. 2007, 50, 1401-1408 (Pubitemid 46496336)
46. Bourguet, C. B.; Sabatino, D.; Lubell, W. D. Benzophenone semicarbazone protection strategy for synthesis of aza-glycine containing aza-peptides Biopolymers 2008, 90, 824-831
47. Bourguet, C. B.; Proulx, C.; Klocek, S.; Sabatino, D.; Lubell, W. D. Solution-phase submonomer diversification of aza-dipeptide building blocks and their application in aza-peptide and aza-DKP synthesis J. Pept. Sci. 2010, 16, 284-296
48. Sabatino, D.; Proulx, C.; Klocek, S.; Bourguet, C. B.; Boeglin, D.; Ong, H.; Lubell, W. D. Exploring side-chain diversity by submonomer solid-phase aza-peptide synthesis Org. Lett. 2009, 11, 3650-3653
49. Bourguet, C. B.; Hou, X.; Chemtob, S.; Lubell, W. D. Influence of Peptide Mimic Turn Stereochemistry on Allosteric Antagonism at the Prostaglandin F2α Receptor. Peptides 2006, Proceedings of the 29th European Peptide Symposium 215; Rolka, K.; Rekowski, P.; Silberring, J., Eds.; The European Peptide Society, 2006; pp 436-437.
50. Bourguet, C. B.; Hou, X.; Chemtob, S.; Lubell, W. D. Exploring the Relationship between Turn Geometry and Allosteric Antagonism of Peptide Mimic Ligands for the Prostaglandin F2 Alpha Receptor. Peptides for Youth, Proceedings of the 20th American Peptide Symposium; Del Valle, S. E.; Escher, E.; Lubell, W. D., Eds.; Advances in Experimental Medicine and Biology, Vol. 611; Springer Science: New York, 2009; pp 271-273.
51. Linder, M. R.; Steurer, S.; Podlech, J. (S)-3-(tert - Butyloxycarbonylamino)-4-phenylbutanoic acid Org. Synth. 2002, 79, 154