Structure-activity relationships of a series of analogues of the RFamide-related peptide 26RFa

Journal of Medicinal Chemistry

Volumn 54, Issue 13, 2011, Pages 4806-4814

  Le Marec, Olivier ^a   Neveu, Cindy ^a   Lefranc, Benjamin ^a   Dubessy, Christophe ^a   Boutin, Jean A ^b   Do Régo, Jean Claude ^a   Costentin, Jean ^a   Tonon, Marie Christine ^a   Tena Sempere, Manuel ^c   Vaudry, Hubert ^a   Leprince, Jérôme ^a  

^a UNIVERSITÉ DE ROUEN   (France)

^b IdRS   (France)

^c UNIVERSITY OF CÓRDOBA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

26RFA (20-26); ALANINE; G PROTEIN COUPLED RECEPTOR; G PROTEIN COUPLED RECEPTOR 103; HEPTAPEPTIDE; NORVALINE; REGULATOR PROTEIN; SERINE; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ANIMAL CELL; ARTICLE; CALCIUM MOBILIZATION; CARBOXY TERMINAL SEQUENCE; MOLECULAR WEIGHT; NONHUMAN; NUCLEOTIDE SEQUENCE; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; ANIMALS; CALCIUM; CHO CELLS; CRICETINAE; CRICETULUS; GTP-BINDING PROTEIN BETA SUBUNITS; LIGANDS; NEUROPEPTIDES; RECEPTORS, G-PROTEIN-COUPLED; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSFECTION;

EID: 79960187918     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200418c     Document Type: Article

References (41)

1. Chartrel, N.; Costentin, J.; Tsutsui, K.; Vaudry, H. The RFamide-Related Peptides. In Handbook of Biologically Active Peptides; Kastin, A.J., Ed.; Elsevier: Amsterdam, 2006; pp 779-786.
2. Chartrel, N.; Dujardin, C.; Anouar, Y.; Leprince, J.; Decker, A.; Clerens, S.; Do-Régo, J. C.; Vandesande, F.; Llorens-Cortes, C.; Costentin, J.; Beauvillain, J. C.; Vaudry, H. Identification of 26RFa, a hypothalamic neuropeptide of the RFamide peptide family with orexigenic activity Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 15247-15252 (Pubitemid 37518047)
3. Fukusumi, S.; Yoshida, H.; Fujii, R.; Maruyama, M.; Komatsu, H.; Habata, Y.; Shintani, Y.; Hinuma, S.; Fujino, M. A new peptidic ligand and its receptor regulating adrenal function in rats J. Biol. Chem. 2003, 278, 46387-46395 (Pubitemid 37452209)
4. Jiang, Y.; Luo, L.; Gustafson, E. L.; Yadav, D.; Laverty, M.; Murgolo, N.; Vassileva, G.; Zeng, M.; Laz, T. M.; Behan, J.; Qiu, P.; Wang, L.; Wang, S.; Bayne, M.; Greene, J.; Monsma, F., Jr.; Zhang, F. L. Identification and characterization of a novel RF-amide peptide ligand for orphan G-protein-coupled receptor SP9155 J. Biol. Chem. 2003, 278, 27652-27657 (Pubitemid 36899952)
5. Ukena, K.; Tachibana, T.; Iwakoshi-Ukena, E.; Saito, Y.; Minakata, H.; Kawaguchi, R.; Osugi, T.; Tobari, Y.; Leprince, J.; Vaudry, H.; Tsutsui, K. Identification, localization, and function of a novel avian hypothalamic neuropeptide, 26RFa, and its cognate receptor, G protein-coupled receptor-103 Endocrinology 2010, 151, 2255-2264
6. Takayasu, S.; Sakurai, T.; Iwasaki, S.; Teranishi, H.; Yamanaka, A.; Williams, S. C.; Iguchi, H.; Kawasawa, Y. I.; Ikeda, Y.; Sakakibara, I.; Ohno, K.; Ioka, R. X.; Murakami, S.; Dohmae, N.; Xie, J.; Suda, T.; Motoike, T.; Ohuchi, T.; Yanagisawa, M.; Sakai, J. A neuropeptide ligand of the G protein-coupled receptor GPR103 regulates feeding, behavioral arousal, and blood pressure in mice Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 7438-7443 (Pubitemid 43727851)
7. Bruzzone, F.; Lectez, B.; Tollemer, H.; Leprince, J.; Dujardin, C.; Rachidi, W.; Chatenet, D.; Baroncini, M.; Beauvillain, J.-C.; Vallarino, M.; Vaudry, H.; Chartrel, N. Anatomical distribution and biochemical characterization of the novel RFamide peptide 26RFa in the human hypothalamus and spinal cord J. Neurochem. 2006, 99, 616-627 (Pubitemid 44477216)
8. Kampe, J.; Wiedmer, P.; Pfluger, P. T.; Castaneda, T. R.; Burget, L.; Mondala, H.; Kerr, J.; Liaw, C.; Oldfield, B. J.; Tschöp, M. H.; Bagnol, D. Effect of central administration of QRFP(26) peptide on energy balance and characterization of a second QRFP receptor in rat Brain Res. 2006, 103, 7438-7443
9. Bruzzone, F.; Lectez, B.; Alexandre, D.; Jégou, S.; Mounien, L.; Tollemer, H.; Chatenet, D.; Leprince, J.; Vallarino, M.; Vaudry, H.; Chartrel, N. Distribution of 26RFa binding sites and GPR103 mRNA in the central nervous system of the rat J. Comp. Neurol. 2007, 503, 573-591 (Pubitemid 47051368)
10. Moriya, R.; Sano, H.; Umeda, T.; Ito, M.; Takahashi, Y.; Matsuda, M.; Ishihara, A.; Kanatani, A.; Iwaasa, H. RFamide peptide QRFP43 causes obesity with hyperphagia and reduced thermogenesis in mice Endocrinology 2006, 147, 2916-2922 (Pubitemid 43764627)
11. Do-Régo, J. C.; Leprince, J.; Chartrel, N.; Vaudry, H.; Costentin, J. Behavioral effects of 26RFamide and related peptides Peptides 2006, 27, 2715-2721 (Pubitemid 44739952)
12. Primeaux, S. D.; Blackmon, C.; Barnes, M. J.; Braymer, H. D.; Bray, G. A. Central administration of the RFamide peptides, QRFP-26 and QRFP-43, increases high fat food intake in rats Peptides 2008, 29, 1994-2000
13. Baribault, H.; Danao, J.; Gupte, J.; Yang, L.; Sun, B.; Richards, W.; Tian, H. The G-protein-coupled receptor GPR103 regulates bone formation Mol. Cell. Biol. 2006, 26, 709-717 (Pubitemid 43089780)
14. Navarro, V. M.; Fernández-Fernández, R.; Nogueiras, R.; Vigo, E.; Tovar, S.; Chartrel, N.; Le Marec, O.; Leprince, J.; Aguilar, E.; Pinilla, L.; Dieguez, C.; Vaudry, H.; Tena-Sempere, M. Novel role of 26RFa, a hypothalamic RFamide orexigenic peptide, as putative regulator of the gonadotropic axis J. Physiol. 2006, 573, 237-249 (Pubitemid 43670871)
15. Patel, S. R.; Murphy, K. G.; Thompson, E. L.; Patterson, M.; Curtis, A. E.; Ghatei, M. A.; Bloom, S. R. Pyroglutamylated RFamide peptide 43 stimulates the hypothalamic-pituitary-gonadal axis via gonadotropin-releasing hormone in rats Endocrinology 2008, 149, 4747-4754
16. Egido, E. M.; Hernández, R.; Leprince, J.; Chartrel, N.; Vaudry, H.; Marco, J.; Silvestre, R. A. 26RFa, a novel orexigenic neuropeptide, inhibits insulin secretion in the rat pancreas Peptides 2007, 28, 725-730 (Pubitemid 46349320)
17. Ukena, K.; Vaudry, H.; Leprince, J.; Tsutsui, K. Molecular evolution and functional characterization of the orexigenic peptide 26RFa and its receptor in vertebrates Cell Tissue Res. 2011, 343, 475-481
18. Acharya, K. R.; Sturrock, E. D.; Riordan, J. F.; Ehlers, M. R. ACE revisited: a new target for structure-based drug design Nat. Rev. Drug Discovery 2003, 2, 891-902 (Pubitemid 37407795)
19. Thuau, R.; Guilhaudis, L.; Ségalas-Milazzo, I.; Chartrel, N.; Oulyadi, H.; Boivin, S.; Fournier, A.; Leprince, J.; Davoust, D.; Vaudry, H. Structural studies on 26RFa, a novel human RFamide-related peptide with orexigenic activity Peptides 2005, 26, 779-789 (Pubitemid 40461659)
20. Li, S. C.; Deber, C. M. A measure of helical propensity for amino acids in membrane environments Nat. Struct. Biol. 1994, 1, 368-373 (Pubitemid 24974862)
21. 35S]GTPγS binding Neuropharmacology 2007, 52, 376-386 (Pubitemid 46123357)
22. Labarrère, P.; Chatenet, D.; Leprince, J.; Marionneau, C.; Loirand, G.; Tonon, M. C.; Dubessy, C.; Scalbert, E.; Pfeiffer, B.; Renard, P.; Calas, B.; Pacaud, P.; Vaudry, H. Structure-activity relationships of human urotensin II and related analogs on rat aortic ring contraction J. Enzyme Inhib. Med. Chem. 2003, 18, 77-88 (Pubitemid 36622124)
23. Chatenet, D.; Dubessy, C.; Leprince, J.; Boularan, C.; Carlier, L.; Ségalas-Milazzo, I.; Guilhaudis, L.; Oulyadi, H.; Davoust, D.; Scalbert, E.; Pfeiffer, B.; Renard, P.; Tonon, M. C.; Lihrmann, I.; Pacaud, P.; Vaudry, H. Structure-activity relationships and structural conformation of a novel urotensin II-related peptide Peptides 2004, 25, 1819-1830 (Pubitemid 39346227)
24. Gautier, B.; Goncalves, V.; Diana, D.; Di Stasi, R.; Teillet, F.; Lenoir, C.; Huguenot, C.; Garbay, C.; Fattorusso, R.; D'Andrea, L. D.; Vidal, M.; Inguimbert, N. Biochemical and structural analysis of the binding determinants of a vascular endothelial growth factor receptor peptidic antagonist J. Med. Chem. 2010, 53, 4428-4440
25. Mazarguil, H.; Gouardères, C.; Tafani, J. A.; Marcus, D.; Kotani, M.; Mollereau, C.; Roumy, M.; Zajac, J. M. Structure-activity relationships of neuropeptide FF: role of C-terminal regions Peptides 2001, 22, 1471-1478 (Pubitemid 32770020)
26. Boyle, R. G.; Downham, R.; Ganguly, T.; Humphries, J.; Smith, J.; Travers, S. Structure-activity studies on prolactin-releasing peptide (PrRP). Analogs of PrRP-(19-31)-peptide J. Pept. Sci. 2005, 11, 161-165 (Pubitemid 40347548)
27. Padmanabhan, S.; Marqusee, S.; Ridgeway, T.; Laue, T. M.; Baldwin, R. L. Relative helix-forming tendencies of nonpolar amino acids Nature 2000, 344, 268-270
28. Arfmann, H. A.; Labitzke, R.; Wagner, K. G. Conformational properties of l -leucine, l -isoleucine, and l -norleucine side chains in l -lysine copolymers Biopolymers 1977, 16, 1815-1826 (Pubitemid 8140484)
29. Chin, W.; Piuzzi, F.; Dognon, J. P.; Dimicoli, I.; Mons, M. Gas-phase models of gamma turns: effect of side-chain/backbone interactions investigated by IR/UV spectroscopy and quantum chemistry J. Chem. Phys. 2005, 123 084301
30. Eipper, B. A.; Stoffers, D. A.; Mains, R. E. The biosynthesis of neuropeptides: peptide alpha-amidation Annu. Rev. Neurosci. 1992, 15, 57-85
31. Fauchère, J. L.; Thurieau, C. Evaluation of the stability of peptides and pseudopeptides as a tool in peptide drug design Adv. Drug Res. 1992, 23, 128-159
32. Mukai, H.; Kawai, K.; Suzuki, Y.; Yamashita, K.; Munekata, E. Stimulation of dog gastropancreatic hormone release by neuromedin B and its analogues Am. J. Physiol. 1987, 252, 765-771
33. Cascieri, M. A.; Huang, R. R.; Fong, T. M.; Cheung, A. H.; Sadowski, S.; Ber, E.; Strader, C. D. Determination of the amino acid residues in substance P conferring selectivity and specificity for the rat neurokinin receptors Mol. Pharmacol. 1992, 41, 1096-1099 (Pubitemid 23026110)
34. Escher, E.; Couture, R.; Poulos, C.; Pinas, N.; Mizrahi, J.; Theodoropoulos, D.; Regoli, D. Structure-activity studies on the C-terminal amide of substance P J. Med. Chem. 1982, 25, 1317-1321 (Pubitemid 13222041)
35. Bourgault, S.; Vaudry, D.; Botia, B.; Couvineau, A.; Laburthe, M.; Vaudry, H.; Fournier, A. Novel stable PACAP analogs with potent activity towards the PAC1 receptor Peptides 2008, 29, 919-932
36. Clairmont, K. B.; Buckholz, T. M.; Pellegrino, C. M.; Buxton, J. M.; Barucci, N.; Bell, A.; Ha, S.; Li, F.; Claus, T. H.; Salhanick, A. I.; Lumb, K. J. Engineering of a VPAC2 receptor peptide agonist to impart dipeptidyl peptidase IV stability and enhance in vivo glucose disposal J. Med. Chem. 2006, 49, 7545-7548 (Pubitemid 44913414)
37. O'Donohue, T. L.; Handelmann, G. E.; Miller, R. L.; Jacobowitz, D. M. N-Acetylation regulates the behavioral activity of α-melanotropin in a multineurotransmitter neuron Science 1982, 215, 1125-1127 (Pubitemid 12114097)
38. Yamamoto, T.; Miyazaki, R.; Yamada, T. Intracerebroventricular administration of 26RFa produces an analgesic effect in the rat formalin test Peptides 2009, 30, 1683-1688
39. Leprince, J.; Gandolfo, P.; Thoumas, J. L.; Patte, C.; Fauchère, J. L.; Vaudry, H.; Tonon, M. C. Structure-activity relationships of a series of analogs of the octadecaneuropeptide ODN on calcium mobilization in rat astrocytes J. Med. Chem. 1998, 41, 4433-4438 (Pubitemid 28516442)
40. Chatenet, D.; Dubessy, C.; Boularan, C.; Scalbert, E.; Pfeiffer, B.; Renard, P.; Lihrmann, I.; Pacaud, P.; Tonon, M. C.; Vaudry, H.; Leprince, J. Structure-activity relationships of a novel series of urotensin II analogs: identification of a urotensin II antagonist J. Med. Chem. 2006, 49, 7234-7238 (Pubitemid 44886009)
41. Rodriguez, M.; Beauverger, P.; Naime, I.; Rique, H.; Ouvry, C.; Souchaud, S.; Dromaint, S.; Suply, Y.; Audinot, V.; Boutin, J. A.; Galizzi, J. P. Cloning and molecular characterization of the novel melanin-concentrating hormone receptor (MCH2) Mol. Pharmacol. 2001, 60, 632-639 (Pubitemid 32900243)