Selective mode of action of guanidine-containing non-peptides at human NPFF receptors

Journal of Medicinal Chemistry

Volumn 55, Issue 13, 2012, Pages 6124-6136

  Findeisen, Maria ^a   Würker, Cäcilia ^a   Rathmann, Daniel ^a   Meier, René ^a   Meiler, Jens ^b   Olsson, Roger ^c,d   Beck Sickinger, Annette G ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c ACADIA PHARMACEUTICALS INC   (United States)

^d UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

1 ADAMANTANECARBONYLARGINYLPHENYLALANYLAMIDE; AC 093; AC 099; AC 216; AC 970; GUANIDINE DERIVATIVE; LIGAND; NALPHA (DIPHENYLACETYL) N (4 HYDROXYBENZYL) DEXTRO ARGININAMIDE; NEUROPEPTIDE FF; NEUROPEPTIDE FF 1 RECEPTOR; NEUROPEPTIDE FF 2 RECEPTOR; NEUROPEPTIDE RECEPTOR; PEPTIDOMIMETIC AGENT; RF 9; UNCLASSIFIED DRUG; VALYLPROLYLASPARAGINYLLEUCYLPROLYLGLUTAMINYLARGINYLPHENYLALANYLAMIDE;

ACIDITY; ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG BINDING SITE; DRUG MECHANISM; DRUG POTENCY; DRUG RECEPTOR BINDING; HUMAN; HUMAN CELL; MOLECULAR DOCKING; MOLECULAR MODEL; MUTANT; NONHUMAN; PEPTIDE SYNTHESIS; SIGNAL TRANSDUCTION;

ADAMANTANE; AMINO ACID SUBSTITUTION; ANIMALS; ARGININE; BINDING SITES; BIOLOGICAL ASSAY; CERCOPITHECUS AETHIOPS; COS CELLS; DIPEPTIDES; DRUG DESIGN; GUANIDINE; HEK293 CELLS; HUMANS; LIGANDS; MICROSCOPY, FLUORESCENCE; MOLECULAR CONFORMATION; PEPTIDOMIMETICS; RECEPTORS, G-PROTEIN-COUPLED; RECEPTORS, NEUROPEPTIDE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84863853873     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm300535s     Document Type: Article

References (55)

1. Yang, H. Y.; Fratta, W.; Majane, E. A.; Costa, E. Isolation, sequencing, synthesis, and pharmacological characterization of two brain neuropeptides that modulate the action of morphine Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 7757-7761 (Pubitemid 16204428)
2. Huang, E. Y.; Li, J. Y.; Tan, P. P.; Wong, C. H.; Chen, J. C. The cardiovascular effects of PFRFamide and PFR(Tic)amide, a possible agonist and antagonist of neuropeptide FF (NPFF) Peptides 2000, 21, 205-210 (Pubitemid 30182482)
3. Laguzzi, R.; Nosjean, A.; Mazarguil, H.; Allard, M. Cardiovascular effects induced by the stimulation of neuropeptide FF receptors in the dorsal vagal complex: an autoradiographic and pharmacological study in the rat Brain Res. 1996, 711, 193-202 (Pubitemid 26081846)
4. Fang, Q.; Wang, Y. Q.; He, F.; Guo, J.; Chen, Q.; Wang, R. Inhibition of neuropeptide FF (NPFF)-induced hypothermia and anti-morphine analgesia by RF9, a new selective NPFF receptors antagonist Regul. Pept. 2008, 147, 45-51
5. Mouledous, L.; Barthas, F.; Zajac, J. M. Opposite control of body temperature by NPFF1 and NPFF2 receptors in mice Neuropeptides 2010, 44, 453-456
6. Kalliomaki, M. L.; Panula, P. Neuropeptide FF, but not prolactin-releasing peptide, mRNA is differentially regulated in the hypothalamic and medullary neurons after salt loading Neuroscience 2004, 124, 81-87 (Pubitemid 38186619)
7. Majane, E. A.; Yang, H. Y. Mammalian FMRF-NH2-like peptide in rat pituitary: decrease by osmotic stimulus Peptides 1991, 12, 1303-1308
8. Findeisen, M.; Rathmann, D.; Beck-Sickinger, A. G. RFamide peptides: structure, function, mechanisms and pharmaceutical potential Pharmaceuticals 2011, 4, 1248-1280
9. Gouarderes, C.; Tafani, J. A.; Zajac, J. M. Affinity of neuropeptide FF analogs to opioid receptors in the rat spinal cord Peptides 1998, 19, 727-730 (Pubitemid 28255009)
10. Raffa, R. B.; Kim, A.; Rice, K. C.; de Costa, B. R.; Codd, E. E.; Rothman, R. B. Low affinity of FMRFamide and four FaRPs (FMRFamide-related peptides), including the mammalian-derived FaRPs F-8-Famide (NPFF) and A-18-Famide, for opioid mu, delta, kappa 1, kappa 2a, or kappa 2b receptors Peptides 1994, 15, 401-404
11. Bonini, J. A.; Jones, K. A.; Adham, N.; Forray, C.; Artymyshyn, R.; Durkin, M. M.; Smith, K. E.; Tamm, J. A.; Boteju, L. W.; Lakhlani, P. P.; Raddatz, R.; Yao, W. J.; Ogozalek, K. L.; Boyle, N.; Kouranova, E. V.; Quan, Y.; Vaysse, P. J.; Wetzel, J. M.; Branchek, T. A.; Gerald, C.; Borowsky, B. Identification and characterization of two G protein-coupled receptors for neuropeptide FF J. Biol. Chem. 2000, 275, 39324-39331 (Pubitemid 32058954)
12. Hinuma, S.; Shintani, Y.; Fukusumi, S.; Iijima, N.; Matsumoto, Y.; Hosoya, M.; Fujii, R.; Watanabe, T.; Kikuchi, K.; Terao, Y.; Yano, T.; Yamamoto, T.; Kawamata, Y.; Habata, Y.; Asada, M.; Kitada, C.; Kurokawa, T.; Onda, H.; Nishimura, O.; Tanaka, M.; Ibata, Y.; Fujino, M. New neuropeptides containing carboxy-terminal RFamide and their receptor in mammals Nat. Cell Biol. 2000, 2, 703-708
13. Liu, Q.; Guan, X. M.; Martin, W. J.; McDonald, T. P.; Clements, M. K.; Jiang, Q.; Zeng, Z.; Jacobson, M.; Williams, D. L., Jr.; Yu, H.; Bomford, D.; Figueroa, D.; Mallee, J.; Wang, R.; Evans, J.; Gould, R.; Austin, C. P. Identification and characterization of novel mammalian neuropeptide FF-like peptides that attenuate morphine-induced antinociception J. Biol. Chem. 2001, 276, 36961-36969
14. Perry, S. J.; Yi-Kung Huang, E.; Cronk, D.; Bagust, J.; Sharma, R.; Walker, R. J.; Wilson, S.; Burke, J. F. A human gene encoding morphine modulating peptides related to NPFF and FMRFamide FEBS Lett. 1997, 409, 426-430 (Pubitemid 27285899)
15. Vilim, F. S.; Aarnisalo, A. A.; Nieminen, M. L.; Lintunen, M.; Karlstedt, K.; Kontinen, V. K.; Kalso, E.; States, B.; Panula, P.; Ziff, E. Gene for pain modulatory neuropeptide NPFF: induction in spinal cord by noxious stimuli Mol. Pharmacol. 1999, 55, 804-811 (Pubitemid 29214599)
16. Gouarderes, C.; Quelven, I.; Mollereau, C.; Mazarguil, H.; Rice, S. Q.; Zajac, J. M. Quantitative autoradiographic distribution of NPFF1 neuropeptide FF receptor in the rat brain and comparison with NPFF2 receptor by using [125I]YVP and [(125)I]EYF as selective radioligands Neuroscience 2002, 115, 349-361 (Pubitemid 35284753)
17. Lameh, J.; Bertozzi, F.; Kelly, N.; Jacobi, P. M.; Nguyen, D.; Bajpai, A.; Gaubert, G.; Olsson, R.; Gardell, L. R. Neuropeptide FF receptors have opposing modulatory effects on nociception J. Pharmacol. Exp. Ther. 2010, 334, 244-254
18. Gaubert, G.; Bertozzi, F.; Kelly, N. M.; Pawlas, J.; Scully, A. L.; Nash, N. R.; Gardell, L. R.; Lameh, J.; Olsson, R. Discovery of selective nonpeptidergic neuropeptide FF2 receptor agonists J. Med. Chem. 2009, 52, 6511-6514
19. Fang, Q.; Guo, J.; He, F.; Peng, Y. L.; Chang, M.; Wang, R. In vivo inhibition of neuropeptide FF agonism by BIBP3226, an NPY Y1 receptor antagonist Peptides 2006, 27, 2207-2213 (Pubitemid 44189628)
20. Mollereau, C.; Mazarguil, H.; Marcus, D.; Quelven, I.; Kotani, M.; Lannoy, V.; Dumont, Y.; Quirion, R.; Detheux, M.; Parmentier, M.; Zajac, J. M. Pharmacological characterization of human NPFF(1) and NPFF(2) receptors expressed in CHO cells by using NPY Y(1) receptor antagonists Eur. J. Pharmacol. 2002, 451, 245-256 (Pubitemid 35254027)
21. Simonin, F.; Schmitt, M.; Laulin, J. P.; Laboureyras, E.; Jhamandas, J. H.; MacTavish, D.; Matifas, A.; Mollereau, C.; Laurent, P.; Parmentier, M.; Kieffer, B. L.; Bourguignon, J. J.; Simonnet, G. RF9, a potent and selective neuropeptide FF receptor antagonist, prevents opioid-induced tolerance associated with hyperalgesia Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 466-471 (Pubitemid 43122424)
22. Findeisen, M.; Rathmann, D.; Beck-Sickinger, A. G. Structure-activity studies of RFamide peptides reveal subtype-selective activation of neuropeptide FF1 and FF2 receptors ChemMedChem 2011, 6, 1081-1093
23. Lindner, D.; van Dieck, J.; Merten, N.; Morl, K.; Gunther, R.; Hofmann, H. J.; Beck-Sickinger, A. G. GPC receptors and not ligands decide the binding mode in neuropeptide Y multireceptor/multiligand system Biochemistry 2008, 47, 5905-5914 (Pubitemid 351770021)
24. Merten, N.; Lindner, D.; Rabe, N.; Rompler, H.; Morl, K.; Schoneberg, T.; Beck-Sickinger, A. G. Receptor subtype-specific docking of Asp6.59 with C-terminal arginine residues in Y receptor ligands J. Biol. Chem. 2007, 282, 7543-7551 (Pubitemid 47093642)
25. Ballesteros, J. A.; Weinstein, H. Integrated methods for the construction of three-dimensional models and computational probing of structure-function relations in G protein-coupled receptors Methods Neurosci. 1995, 25, 366-428
26. Davis, I. W.; Baker, D. RosettaLigand docking with full ligand and receptor flexibility J. Mol. Biol. 2009, 385, 381-392
27. Mollereau, C.; Gouarderes, C.; Dumont, Y.; Kotani, M.; Detheux, M.; Doods, H.; Parmentier, M.; Quirion, R.; Zajac, J. M. Agonist and antagonist activities on human NPFF(2) receptors of the NPY ligands GR231118 and BIBP3226 Br. J. Pharmacol. 2001, 133, 1-4 (Pubitemid 32500444)
28. Engstrom, M.; Wurster, S.; Savola, J. M.; Panula, P. Functional properties of Pfr(Tic)amide and BIBP3226 at human neuropeptide FF2 receptors Peptides 2003, 24, 1947-1954 (Pubitemid 38177631)
29. Rudolf, K.; Eberlein, W.; Engel, W.; Wieland, H. A.; Willim, K. D.; Entzeroth, M.; Wienen, W.; Beck-Sickinger, A. G.; Doods, H. N. The first highly potent and selective non-peptide neuropeptide Y Y1 receptor antagonist: BIBP3226 Eur. J. Pharmacol. 1994, 271, R11-R13
30. Sautel, M.; Rudolf, K.; Wittneben, H.; Herzog, H.; Martinez, R.; Munoz, M.; Eberlein, W.; Engel, W.; Walker, P.; Beck-Sickinger, A. G. Neuropeptide Y and the nonpeptide antagonist BIBP 3226 share an overlapping binding site at the human Y1 receptor Mol. Pharmacol. 1996, 50, 285-292 (Pubitemid 26265132)
31. McAllister, S. D.; Tao, Q.; Barnett-Norris, J.; Buehner, K.; Hurst, D. P.; Guarnieri, F.; Reggio, P. H.; Nowell Harmon, K. W.; Cabral, G. A.; Abood, M. E. A critical role for a tyrosine residue in the cannabinoid receptors for ligand recognition Biochem. Pharmacol. 2002, 63, 2121-2136 (Pubitemid 34756677)
32. Berg, K. A.; Maayani, S.; Goldfarb, J.; Scaramellini, C.; Leff, P.; Clarke, W. P. Effector pathway-dependent relative efficacy at serotonin type 2A and 2C receptors: evidence for agonist-directed trafficking of receptor stimulus Mol. Pharmacol. 1998, 54, 94-104 (Pubitemid 28337591)
33. McLaughlin, J. N.; Shen, L.; Holinstat, M.; Brooks, J. D.; Dibenedetto, E.; Hamm, H. E. Functional selectivity of G protein signaling by agonist peptides and thrombin for the protease-activated receptor-1 J. Biol. Chem. 2005, 280, 25048-25059 (Pubitemid 40934596)
34. Urban, J. D.; Clarke, W. P.; von Zastrow, M.; Nichols, D. E.; Kobilka, B.; Weinstein, H.; Javitch, J. A.; Roth, B. L.; Christopoulos, A.; Sexton, P. M.; Miller, K. J.; Spedding, M.; Mailman, R. B. Functional selectivity and classical concepts of quantitative pharmacology J. Pharmacol. Exp. Ther. 2007, 320, 1-13 (Pubitemid 46025713)
35. Raehal, K. M.; Schmid, C. L.; Groer, C. E.; Bohn, L. M. Functional selectivity at the mu-opioid receptor: implications for understanding opioid analgesia and tolerance Pharmacol. Rev. 2011, 63, 1001-1019
36. Robb, S.; Cheek, T. R.; Hannan, F. L.; Hall, L. M.; Midgley, J. M.; Evans, P. D. Agonist-specific coupling of a cloned Drosophila octopamine/tyramine receptor to multiple second messenger systems EMBO J. 1994, 13, 1325-1330 (Pubitemid 24090213)
37. Rihakova, L.; Quiniou, C.; Hamdan, F. F.; Kaul, R.; Brault, S.; Hou, X.; Lahaie, I.; Sapieha, P.; Hamel, D.; Shao, Z.; Gobeil, F., Jr.; Hardy, P.; Joyal, J. S.; Nedev, H.; Duhamel, F.; Beauregard, K.; Heveker, N.; Saragovi, H. U.; Guillon, G.; Bouvier, M.; Lubell, W. D.; Chemtob, S. VRQ397 (CRAVKY): a novel noncompetitive V2 receptor antagonist Am. J. Physiol.: Regul., Integr. Comp. Physiol. 2009, 297, R1009-1018
38. Kilts, J. D.; Connery, H. S.; Arrington, E. G.; Lewis, M. M.; Lawler, C. P.; Oxford, G. S.; OMalley, K. L.; Todd, R. D.; Blake, B. L.; Nichols, D. E.; Mailman, R. B. Functional selectivity of dopamine receptor agonists. II. Actions of dihydrexidine in D2L receptor-transfected MN9D cells and pituitary lactotrophs J. Pharmacol. Exp. Ther. 2002, 301, 1179-1189 (Pubitemid 34595112)
39. Mottola, D. M.; Kilts, J. D.; Lewis, M. M.; Connery, H. S.; Walker, Q. D.; Jones, S. R.; Booth, R. G.; Hyslop, D. K.; Piercey, M.; Wightman, R. M.; Lawler, C. P.; Nichols, D. E.; Mailman, R. B. Functional selectivity of dopamine receptor agonists. I. Selective activation of postsynaptic dopamine D2 receptors linked to adenylate cyclase J. Pharmacol. Exp. Ther. 2002, 301, 1166-1178 (Pubitemid 34595111)
40. Ghanouni, P.; Gryczynski, Z.; Steenhuis, J. J.; Lee, T. W.; Farrens, D. L.; Lakowicz, J. R.; Kobilka, B. K. Functionally different agonists induce distinct conformations in the G protein coupling domain of the beta 2 adrenergic receptor J. Biol. Chem. 2001, 276, 24433-24436
41. Ebersole, B. J.; Visiers, I.; Weinstein, H.; Sealfon, S. C. Molecular basis of partial agonism: orientation of indoleamine ligands in the binding pocket of the human serotonin 5-HT2A receptor determines relative efficacy Mol. Pharmacol. 2003, 63, 36-43 (Pubitemid 36043806)
42. Kurrasch-Orbaugh, D. M.; Watts, V. J.; Barker, E. L.; Nichols, D. E. Serotonin 5-hydroxytryptamine 2A receptor-coupled phospholipase C and phospholipase A2 signaling pathways have different receptor reserves J. Pharmacol. Exp. Ther. 2003, 304, 229-237 (Pubitemid 36008933)
43. Gouarderes, C.; Mazarguil, H.; Mollereau, C.; Chartrel, N.; Leprince, J.; Vaudry, H.; Zajac, J. M. Functional differences between NPFF1 and NPFF2 receptor coupling: high intrinsic activities of RFamide-related peptides on stimulation of [35S]GTPgammaS binding Neuropharmacology 2007, 52, 376-386 (Pubitemid 46123357)
44. Lebon, G.; Warne, T.; Edwards, P. C.; Bennett, K.; Langmead, C. J.; Leslie, A. G.; Tate, C. G. Agonist-bound adenosine A2A receptor structures reveal common features of GPCR activation Nature 2011, 474, 521-525
45. Wu, B.; Chien, E. Y.; Mol, C. D.; Fenalti, G.; Liu, W.; Katritch, V.; Abagyan, R.; Brooun, A.; Wells, P.; Bi, F. C.; Hamel, D. J.; Kuhn, P.; Handel, T. M.; Cherezov, V.; Stevens, R. C. Structures of the CXCR4 chemokine GPCR with small-molecule and cyclic peptide antagonists Science 2010, 330, 1066-1071
46. Cherezov, V.; Rosenbaum, D. M.; Hanson, M. A.; Rasmussen, S. G.; Thian, F. S.; Kobilka, T. S.; Choi, H. J.; Kuhn, P.; Weis, W. I.; Kobilka, B. K.; Stevens, R. C. High-resolution crystal structure of an engineered human beta2-adrenergic G protein-coupled receptor Science 2007, 318, 1258-1265 (Pubitemid 350172884)
47. Okada, T.; Sugihara, M.; Bondar, A. N.; Elstner, M.; Entel, P.; Buss, V. The retinal conformation and its environment in rhodopsin in light of a new 2.2 Å crystal structure J. Mol. Biol. 2004, 342, 571-583 (Pubitemid 39149759)
48. Warne, T.; Moukhametzianov, R.; Baker, J. G.; Nehme, R.; Edwards, P. C.; Leslie, A. G.; Schertler, G. F.; Tate, C. G. The structural basis for agonist and partial agonist action on a beta(1)-adrenergic receptor Nature 2011, 469, 241-244
49. Shimamura, T.; Shiroishi, M.; Weyand, S.; Tsujimoto, H.; Winter, G.; Katritch, V.; Abagyan, R.; Cherezov, V.; Liu, W.; Han, G. W.; Kobayashi, T.; Stevens, R. C.; Iwata, S. Structure of the human histamine H1 receptor complex with doxepin Nature 2011, 475, 65-70
50. Murakami, M.; Kouyama, T. Crystal structure of squid rhodopsin Nature 2008, 453, 363-367 (Pubitemid 351693128)
51. Chien, E. Y.; Liu, W.; Zhao, Q.; Katritch, V.; Han, G. W.; Hanson, M. A.; Shi, L.; Newman, A. H.; Javitch, J. A.; Cherezov, V.; Stevens, R. C. Structure of the human dopamine D3 receptor in complex with a D2/D3 selective antagonist Science 2010, 330, 1091-1095
52. Canutescu, A. A.; Dunbrack, R. L., Jr. Cyclic coordinate descent: a robotics algorithm for protein loop closure Protein Sci. 2003, 12, 963-972 (Pubitemid 36505431)
53. Barth, P.; Schonbrun, J.; Baker, D. Toward high-resolution prediction and design of transmembrane helical protein structures Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 15682-15687 (Pubitemid 350035360)
54. Fleishman, S. J.; Leaver-Fay, A.; Corn, J. E.; Strauch, E. M.; Khare, S. D.; Koga, N.; Ashworth, J.; Murphy, P.; Richter, F.; Lemmon, G.; Meiler, J.; Baker, D. RosettaScripts: a scripting language interface to the Rosetta macromolecular modeling suite PLoS One 2011, 6, e20161
55. Baxter, C. A.; Murray, C. W.; Clark, D. E.; Westhead, D. R.; Eldridge, M. D. Flexible docking using Tabu search and an empirical estimate of binding affinity Proteins 1998, 33, 367-382 (Pubitemid 28516342)