Discovery and cardioprotective effects of the first non-peptide agonists of the G protein-coupled prokineticin receptor-1

PLoS ONE

Volumn 10, Issue 4, 2015, Pages

  Gasser, Adeline ^a   Brogi, Simone ^b   Urayama, Kyoji ^a   Nishi, Toshishide ^a,c   Kurose, Hitoshi ^c   Tafi, Andrea ^b   Ribeiro, Nigel ^a   Désaubry, Laurent ^a   Nebigil, Canan G ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITY OF SIENA   (Italy)

^c KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

MUS;

BENZAMIDE DERIVATIVE; CALCIUM; G PROTEIN COUPLED RECEPTOR; PEPTIDE; PKR1 PROTEIN, MOUSE; PROTECTIVE AGENT; PYRIDINE DERIVATIVE;

AGONISTS; ANIMAL; BINDING SITE; BIOLOGY; BLOOD PRESSURE; C57BL MOUSE; CELL CULTURE; CHEMISTRY; CHO CELL LINE; CONFOCAL MICROSCOPY; CRICETULUS; CYTOLOGY; DISEASE MODEL; DRUG EFFECTS; ECHOCARDIOGRAPHY; ENDOTHELIUM CELL; GENETICS; HAMSTER; MALE; METABOLISM; MOLECULAR DOCKING; MOUSE; MYOCARDIAL INFARCTION; PATHOLOGY; SIGNAL TRANSDUCTION;

ANIMALS; BENZAMIDES; BINDING SITES; BLOOD PRESSURE; CALCIUM; CELLS, CULTURED; CHO CELLS; COMPUTATIONAL BIOLOGY; CRICETINAE; CRICETULUS; DISEASE MODELS, ANIMAL; ECHOCARDIOGRAPHY; ENDOTHELIAL CELLS; MALE; MICE; MICE, INBRED C57BL; MICROSCOPY, CONFOCAL; MOLECULAR DOCKING SIMULATION; MYOCARDIAL INFARCTION; PEPTIDES; PROTECTIVE AGENTS; PYRIDINES; RECEPTORS, G-PROTEIN-COUPLED; SIGNAL TRANSDUCTION;

EID: 84926674955     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0121027     Document Type: Article

References (48)

1. Guazzi M, Faggiano P, Mureddu GF, Faden G, Niebauer J, Temporelli PL. Worksite health and wellness in theeuropean union. Prog Cardiovasc Dis. 2014;56:508-514 doi: 10.1016/j.pcad.2013.11.003 PMID: 24607015
2. Masuda Y, Takatsu Y, Terao Y, Kumano S, Ishibashi Y, Suenaga M, et al. Isolation and identification of eg-vegf/prokineticins as cognate ligands for two orphan g-protein-coupled receptors. Biochem. Biophys. Res. Commun. 2002;293:396-402 PMID: 12054613
3. Lin DC, Bullock CM, Ehlert FJ, Chen JL, Tian H, Zhou QY. Identification and molecular characterization of two closely related g protein-coupled receptors activated by prokineticins/endocrine gland vascular endothelial growth factor. J Biol Chem. 2002;277:19276-19280 PMID: 11886876
4. Nebigil CG. Prokineticin receptors in cardiovascular function: Foeorfriend? Trends Cardiovasc Med. 2009;19:55-60 doi: 10.1016/j.tcm.2009.04.007 PMID: 19577713
5. Boulberdaa M, Turkeri G, Urayama K, Dormishian M, Szatkowski C, Zimmer L, et al. Genetic inactivation of prokineticin receptor-1 leads to heart and kidney disorders. Arterioscler Thromb Vasc Biol. 2011;31:842-850 doi: 10.1161/ATVBAHA.110.222323 PMID: 21273561
6. Urayama K, Guilini C, Messaddeq N, Hu K, Steenman M, Kurose H, et al. The prokineticin receptor-1 (gpr73) promotes cardiomyocyte survival and angiogenesis. FASEB J. 2007;21:2980-2993 PMID: 17442730
7. Nguyen T, Gasser A, Nebigil CG. Role of prokineticin receptor-1 in epicardial progenitor cells. J. Dev. Biol. 2013;1:20-31
8. Urayama K, Dedeoglu DB, Guilini C, Frantz S, Ertl G, Messaddeq N, et al. Transgenic myocardial overexpression of prokineticin receptor-2 (gpr73b) induces hypertrophy and capillary vessel leakage. Cardiovasc Res. 2009;81:28-37 doi: 10.1093/cvr/cvn251 PMID: 18806277
9. Urayama K, Guilini C, Turkeri G, Takir S, Kurose H, Messaddeq N, et al. Prokineticin receptor-1 induces neovascularization and epicardial-derived progenitor cell differentiation. Arterioscler Thromb Vasc Biol. 2008;28:841-849 doi: 10.1161/ATVBAHA.108.162404 PMID: 18421008
10. Guilini C, Urayama K, Turkeri G, Dedeoglu DB, Kurose H, Messaddeq N, et al. Divergent roles of prokineticin receptors in the endothelial cells: Angiogenesis and fenestration. Am J Physiol Heart Circ Physiol. 2010;298:H844-852 doi: 10.1152/ajpheart.00898.2009 PMID: 20023120
11. Chen J, Kuei C, Sutton S, Wilson S, Yu J, Kamme F, et al. Identification and pharmacological characterization of prokineticin 2 beta as a selective ligand for prokineticin receptor 1. Mol. Pharmacol. 2005;67:2070-6. PMID: 15772293
12. Balboni G, Lazzari I, Trapella C, Negri L, Lattanzi R, Giannini E, et al. Triazine compounds as antagonists at bv8-prokineticin receptors. J Med Chem. 2008;51:7635-7639
13. Bullock CM, Li JD, Zhou QY. Structural determinants required forthebioactivities of prokineticins and identification of prokineticin receptor antagonists. Mol Pharmacol. 2004;65:582-588 PMID: 14978236
14. Carroll C, Goldby A, Teall M, inventors; Takeda Pharmaceutical Company Limited, Takeda Cambridge Limited, assignee. Sulfonyl piperidine derivatives and their use for treating prokineticin mediated diseases. WO2013179024A1; United States patent US20130324576. 2013 Dec. 5.
15. Congiu C, Onnis V, Deplano A, Salvadori S, Marconi V, Maftei D, et al. A new convenient synthetic method and preliminary pharmacological characterization of triazinediones as prokineticin receptor antagonists. Eur J Med Chem. 2014;81:334-340 doi: 10.1016/j.ejmech.2014.05.030 PMID: 24852280
16. Zhou QY, Li JD, Huang Q, inventors; The Regents Of The University Of California, assignee. Prokineticin receptor antagonists and uses thereof. WO2010077976A3; United States patent US8722896B2. 2014 may 13.
17. Jacoby E, Bouhelal R, Gerspacher M, Seuwen K. The 7 tm g-protein-coupled receptor target family. Chem Med Chem. 2006;1:761-782
18. Carlsson J, Coleman RG, Setola V, Irwin JJ, Fan H, Schlessinger A, et al. Ligand discovery from a dopamine d3 receptor homology model and crystal structure. Nat Chem Biol. 2011;7:769-778 doi: 10. 1038/nchembio.662 PMID: 21926995
19. Katritch V, Jaakola V-P, Lane JR, Lin J, Ijzerman AP, Yeager M, et al. Structure-based discovery of novel chemotypes for adenosine a2a receptor antagonists. J. Med. Chem. 2010;53:1799-1809
20. Kolb P, Rosenbaum DM, Irwin JJ, Fung JJ, Kobilka BK, Shoichet BK. Structure-based discovery of beta2-adrenergic receptor ligands. Proc Natl Acad Sci U S A. 2009;106:6843-6848 doi: 10.1073/pnas. 0812657106 PMID: 19342484
21. Kooistra AJ, Roumen L, Leurs R, de Esch IJ, de Graaf C. From heptahelical bundle to hits from the haystack: Structure-based virtual screening for gpcr ligands. Methods Enzymol. 2013;522:279-336 doi: 10.1016/B978-0-12-407865-9.00015-7 PMID: 23374191
22. Li YY, Hou TJ, Goddard WA 3rd. Computational modeling of structure-function of g protein-coupled receptors with applications for drug design. Curr Med Chem. 2010;17:1167-1180 PMID: 20158474
23. Miserey-Lenkei S, Parnot C, Bardin S, Corvol P, Clauser E. Constitutive internalization of constitutively active agiotensin ii at (1a) receptor mutants is blocked by inverse agonists. J Biol Chem. 2002;277:5891-5901
24. Cheng H, Song LS, Shirokova N, Gonzalez A, Lakatta EG, Rios E, et al. Amplitude distribution of calcium sparks in confocal images: Theory and studies with an automatic detection method. Biophys J. 1999;76:606-617 PMID: 9929467
25. Grynkiewicz G, Poenie M, Tsien RY. A new generation of ca2+ indicators with greatly improved fluorescence properties. J Biol Chem. 1985;260:3440-3450
26. Dormishian M, Turkeri G, Urayama K, Nguyen TL, Boulberdaa M, Messaddeq N, et al. Prokineticin receptor-1 is a new regulator of endothelial insulin uptake and capillary formation to control insulin sensitivity and cardiovascular and kidney functions. J Am Heart Assoc. 2013;2:e000411 doi: 10.1161/JAHA.113.000411 PMID: 24152983
27. CP Hmodels 3.2 Server. Technical University of Denmark: Center for Biological Sequence Analysis. Available: http://www.cbs.dtu.dk/services/CPHmodels/. Accessed January, 2014.
28. Nielsen M, Lundegaard C, Lund O, Petersen TN. Cphmodels-3.0-remote homology modeling using structure-guided sequence profiles. Nucleic Acids Res. 2010;38:W576-W581 doi: 10.1093/nar/gkq535 PMID: 20542909
29. Cappelli A, Manini M, Valenti S, Castriconi F, Giuliani G, Anzini M, et al. Synthesis and structure-activity relationship studies in serotonin 5-ht1a receptor agonists based on fused pyrrolidone scaffolds. Eur. J. Med. Chem. 2013;63:85-94 doi: 10.1016/j.ejmech.2013.01.044 PMID: 23466604
30. Gemma S, Brogi S, Patil PR, Giovani S, Lamponi S, Cappelli A, et al. From (+)-epigallocatechin gallate to a simplified synthetic analogue as a cytoadherence inhibitor for p. Falciparum. RSC Adv. 2014;4:4769-4781
31. Giovani S, Penzo M, Brogi S, Brindisi M, Gemma S, Novellino E, et al. Rational design of the first difluorostatone-based pfsub1 inhibitors. Bioorg Med Chem Lett. 2014;24:3582-3586 doi: 10.1016/j.bmcl. 2014.05.044 PMID: 24909083
32. Cherezov V, Rosenbaum DM, Hanson MA, Rasmussen SG, Thian FS, Kobilka TS, et al. High-resolution crystal structure of an engineered human beta2-adrenergic g protein-coupled receptor. Science. 2007;318:1258-1265 PMID: 17962520
33. Jaakola VP, Griffith MT, Hanson MA, Cherezov V, Chien EY, Lane JR, et al. The 2.6 angstrom crystal structure of a human a2a adenosine receptor bound to an antagonist. Science. 2008;322:1211-1217 doi: 10.1126/science.1164772 PMID: 18832607
34. Rasmussen SG, Choi HJ, Rosenbaum DM, Kobilka TS, Thian FS, Edwards PC, et al. Crystal structure of the human beta2 adrenergic g-protein-coupled receptor. Nature. 2007;450:383-387 PMID: 17952055
35. Warne T, Serrano-Vega MJ, Baker JG, Moukhametzianov R, Edwards PC, Henderson R, et al. Structure of a beta1-adrenergic g-protein-coupled receptor. Nature. 2008;454:486-491 doi: 10.1038/nature07101 PMID: 18594507
36. Levit A, Yarnitzky T, Wiener A, Meidan R, Niv MY. Modeling of human prokineticin receptors: Interactions with novel small-molecule binders and potential off-target drugs. PLoS One. 2011;6:e27990 doi: 10.1371/journal.pone.0027990 PMID: 22132188
37. Jones G, Willett P, Glen RC A genetic algorithm for flexible molecular overlay and pharmacophore elucidation. Journal of computer-aided molecular design. 1995;9:532-549 PMID: 8789195
38. Le Couter J, Kowalski J, Foster J, Hass P, Zhang Z, Dillard-Telm L, et al. Identification of an angiogenic mitogen selective for endocrine gland endothelium. Nature. 2001;412:877-884 PMID: 11528470
39. Le Couter J, Lin R, Tejada M, Frantz G, Peale F, Hillan KJ, et al. The endocrine-gland-derived vegfhomologue bv8 promotes angiogenesis in the testis: Localization of bv8 receptors to endothelial cells. Proc Natl Acad Sci U S A. 2003;100:2685-2690 PMID: 12604792
40. Kisliouk T, Podlovni H, Spanel-Borowski K, Ovadia O, Zhou QY, Meidan R. Prokineticins (endocrine gland-derived vascular endothelial growth factor and bv8) in the bovine ovary: Expression and role as mitogens and survival factors for corpus luteum-derived endothelial cells. Endocrinology. 2005;146:3950-3958 PMID: 15932929
41. Martin C, Balasubramanian R, Dwyer AA, Au MG, Sidis Y, Kaiser UB, Seminara SB, et al. The role of the prokineticin 2 pathway in human reproduction: Evidence from the study of human and murine gene mutations. Endocr Rev. 2011;32:225-246 doi: 10.1210/er.2010-0007 PMID: 21037178
42. Dai W, You Z, Zhou H, Zhang J, Hu Y. Structure-function relationships of the human bitter taste receptor htas2r1: Insights from molecular modeling studies. J Recept Signal Transduct Res. 2011;31:229-240 doi: 10.3109/10799893.2011.578141 PMID: 21619450
43. Wootten D, Christopoulos A, Sexton PM. Emerging paradigms ingpcrallostery: Implications for drug discovery. Nat Rev Drug Discov. 2013;12:630-644 doi: 10.1038/nrd4052 PMID: 23903222
44. Conn PJ, Christopoulos A, Lindsley CW. Allosteric modulators of gpcrs: A novel approach for the treatment of cns disorders. Nat Rev Drug Discov. 2009;8:41-54 doi: 10.1038/nrd2760 PMID: 19116626
45. De Vita RJ. Aminoquinoline melanin-concentrating hormone 1-receptor (mch1-r) antagonists. CurrTop MedChem. 2007;7:1433-1439 PMID: 17897030
46. Wang L, Martin B, Brenneman R, Luttrell LM, Maudsley S. Allosteric modulators of g protein-coupled receptors: Future therapeutics for complex physiological disorders. J Pharmacol Exp Ther. 2009;331:340-348
47. Le Couter J, Zlot C, Tejada M, Peale F, Ferrara N. Bv8 and endocrine gland-derived vascular endothelial growth factor stimulate hematopoiesis and hematopoietic cell mobilization. Proc Natl Acad Sci U S A. 2004;101:16813-16818 PMID: 15548611
48. Szatkowski C, Vallet J, Dormishian M, Messaddeq N, Valet P, Boulberdaa M, et al. Prokineticin receptor 1 as a novel suppressor of preadipocyte proliferation and differentiation to control obesity. PLoS One. 2013;8:81175 doi: 10.1371/journal.pone.0081175 PMID: 24324673