Activation of neuropeptide FF receptors by kisspeptin receptor ligands

ACS Medicinal Chemistry Letters

Volumn 2, Issue 1, 2011, Pages 53-57

  Oishi, Shinya ^a   Misu, Ryosuke ^a   Tomita, Kenji ^a   Setsuda, Shohei ^a   Masuda, Ryo ^a   Ohno, Hiroaki ^a   Naniwa, Yousuke ^b   Ieda, Nahoko ^b   Inoue, Naoko ^b   Ohkura, Satoshi ^b   Uenoyama, Yoshihisa ^b   Tsukamura, Hiroko ^b   Maeda, Kei Ichiro ^b   Hirasawa, Akira ^a   Tsujimoto, Gozoh ^a   Fujii, Nobutaka ^a  

^a KYOTO UNIVERSITY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

GPR54; kisspeptin; Neuropeptide FF receptors; NPFFR1; NPFFR2

Indexed keywords

G PROTEIN COUPLED RECEPTOR 54; GONADORELIN; KISSPEPTIN 10; NEUROPEPTIDE FF RECEPTOR 1; NEUROPEPTIDE FF RECEPTOR 2; RECEPTOR PROTEIN; UNCLASSIFIED DRUG;

ARTICLE; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN INTERACTION; PROTEIN LOCALIZATION;

EID: 78651519422     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml1002053     Document Type: Article

References (30)

1. For a recent review on kisspeptins, see Oakley, A. E.; Clifton, D. K.; Steiner, R. A. Kisspeptin Signaling in the Brain Endocr. Rev. 2009, 30, 713-743
2. Ohtaki, T.; Shintani, Y.; Honda, S.; Matsumoto, H.; Hori, A.; Kanehashi, K.; Terao, Y.; Kumano, S.; Takatsu, Y.; Masuda, Y.; Ishibashi, Y.; Watanabe, T.; Asada, M.; Yamada, T.; Suenaga, M.; Kitada, C.; Usuki, S.; Kurokawa, T.; Onda, H.; Nishimura, O.; Fujino, M. Metastasis Suppressor Gene KiSS-1 Encodes Peptide Ligand of a G-protein-coupled Receptor Nature 2001, 411, 613-617
3. Dhillo, W. S.; Chaudhri, O. B.; Patterson, M.; Thompson, E. L.; Murphy, K. G.; Badman, M. K.; McGowan, B. M.; Amber, V.; Patel, S.; Ghatei, M. A.; Bloom, S. R. Kisspeptin-54 Stimulates the Hypothalamic-pituitary Gonadal Axis in Human Males J. Clin. Endocrinol. Metab. 2005, 90, 6609-6615
4. Matsui, H.; Takatsu, Y.; Kumano, S.; Matsumoto, H.; Ohtaki, T. Peripheral Administration of Metastin Induces Marked Gonadotropin Release And Ovulation in the Rat Biochem. Biophys. Res. Commun. 2004, 320, 383-388
5. Shahab, M.; Mastronardi, C.; Seminara, S. B.; Crowley, W. F.; Ojeda, S. R.; Plant, T. M. Increased Hypothalamic GPR54 Signaling: A Potential Mechanism for Initiation of Puberty in Primates Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 2129-2134
6. Seminara, S. B.; Messager, S.; Chatzidaki, E. E.; Thresher, R. R.; Acierno, J. S., Jr.; Shagoury, J. K.; Bo-Abbas, Y.; Kuohung, W.; Schwinof, K. M.; Hendrick, A. G.; Zahn, D.; Dixon, J.; Kaiser, U. B.; Slaugenhaupt, S. A.; Gusella, J. F.; O'Rahilly, S.; Carlton, M. B. L.; Crowley, W. F., Jr.; Aparicio, S. A. J. R.; Colledge, W. H. The GPR54 Gene as a Regulator of Puberty N. Engl. J. Med. 2003, 349, 1614-1627
7. De Roux, N.; Genin, E.; Carel, J.-C.; Matsuda, F.; Chaussain, J.-L.; Milgrom, E. Hypogonadotropic Hypogonadism Due to Loss of Function of the KiSS1-derived Peptide Receptor GPR54 Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 10972-10976
8. Funes, S.; Hedrick, J. A.; Vassileva, G.; Markowitz, L.; Abbondanzo, S.; Golovko, A.; Yang, S.; Monsma, F. J.; Gustafson, E. L. The KiSS-1 Receptor GPR54 Is Essential for the Development of the Murine Reproductive System Biochem. Biophys. Res. Commun. 2003, 312, 1357-1363
9. Gutiérrez-Pascual, E.; Leprince, J.; Martínez-Fuentes, A. J.; Ségalas-Milazzo, I.; Pineda, R.; Roa, J.; Duran-Prado, M.; Guilhaudis, L.; Desperrois, E.; Lebreton, A.; Pinilla, L.; Tonon, M. C.; Malagón, M. M.; Vaudry, H.; Tena-Sempere, M.; Castaño, J. P. In Vivo And In Vitro Structure-activity Relationships And Structural Conformation of Kisspeptin-10-related Peptides Mol. Pharmacol. 2009, 76, 58-67
10. Pheng, V.; Uenoyama, Y.; Homma, T.; Inamoto, Y.; Takase, K.; Yoshizawa-Kumagaye, K.; Isaka, S.; Watanabe, T. X.; Ohkura, S.; Tomikawa, J.; Maeda, K.; Tsukamura, H. Potencies of Centrally-or Peripherally-injected Full-length Kisspeptin Or Its C-terminal Decapeptide on LH Release in Intact Male Rats J. Reprod. Dev. 2009, 55, 378-382
11. Orsini, M. J.; Klein, M. A.; Beavers, M. P.; Connolly, P. J.; Middleton, S. A.; Mayo, K. H. Metastin (KiSS-1) Mimetics Identified from Peptide Structure-Activity Relationship-derived Pharmacophores And Directed Small Molecule Database Screening J. Med. Chem. 2007, 50, 462-471
12. Roseweir, A. K.; Kauffman, A. S.; Smith, J. T.; Guerriero, K. A.; Morgan, K.; Pielecka-Fortuna, J.; Pineda, R.; Gottsch, M. L.; Tena-Sempere, M.; Moenter, S. M.; Terasawa, E.; Clarke, I. J.; Steiner, R. A.; Millar, R. P. Discovery of Potent Kisspeptin Antagonists Delineate Physiological Mechanisms of Gonadotropin Regulation J. Neurosci. 2009, 29, 3920-3929
13. Kobayashi, T.; Sasaki, S.; Tomita, N.; Fukui, S.; Nakayama, M.; Kiba, A.; Kusaka, M.; Matsumoto, S. I.; Yamaguchi, M.; Itoh, F.; Baba, A. 2-Acylamino-4,6-diphenylpyridine Derivatives as Novel GPR54 Antagonists with Good Brain Exposure And In Vivo Efficacy for Plasma LH Level in Male Rats Bioorg. Med. Chem. 2010, 18, 5157-5171 and the references therein.
14. Niida, A.; Wang, Z.; Tomita, K.; Oishi, S.; Tamamura, H.; Otaka, A.; Navenot, J.-M.; Broach, J. R.; Peiper, S. C.; Fujii, N. Design Aand Synthesis of Downsized Metastin(45-54) Analogs with Maintenance of High GPR54 Agonistic Activity Bioorg. Med. Chem. Lett. 2006, 16, 134-137
15. Tomita, K.; Oishi, S.; Cluzeau, J.; Ohno, H.; Navenoto, J.-M.; Wang, Z.; Peiper, S. C.; Akamatsu, M.; Fujii, N. SAR And QSAR Studies on the N-Terminally Acylated Pentapeptide Agonists for GPR54 J. Med. Chem. 2007, 50, 3222-3228
16. Tomita, K.; Oishi, S.; Ohno, H.; Peiper, S. C.; Fujii, N. Development of Novel G-protein-coupled Receptor 54 Agonists with Resistance to Degradation by Matrix Metalloproteinase J. Med. Chem. 2008, 51, 7645-7649
17. Takino, T.; Koshikawa, N.; Miyamori, H.; Tanaka, M.; Takuma, S.; Okada, Y.; Seiki, M.; Sato, H. Cleavage of Metastasis Suppressor Gene Product KiSS-1 Protein/metastin by Matrix Metalloproteinases Oncogene 2003, 22, 4617-4626
18. Inoue, N.; Tomikawa, J.; Sasaki, Y.; Uchida, A.; Oishi, S.; Fujii, N.; Uenoyama, Y.; Yamamoto, N.; Maeda, K. I.; Tsukamura, H. Kiss1 cDNA Cloning And Induction of Ovulation by Peripheral Administration of Various Kisspeptins in the Musk Shrew (Suncus murinus), a Reflex Ovulator. Presented at the 43rd annual meeting of the society for the study of reproduction, Milwaukee. WI, July 30-August 3, 2010; Abstract; p 128.
19. Lyubimov, Y.; Engstrom, M.; Wurster, S.; Savola, J. M.; Korpi, E. R.; Panula, P. Human Kisspeptins Activate Neuropeptide FF2 Receptor Neuroscience 2010, 170, 117-122
20. Lee, D. K.; Nguyen, T.; O'Neill, G. P.; Cheng, R.; Liu, Y.; Howard, A. D.; Coulombe, N.; Tan, C. P.; Tang-Nguyen, A.-T.; George, S. R.; O'Dowd, B. F. Discovery of a Receptor Related to the Galanin Receptors FEBS Lett. 1999, 446, 103-107
21. Hirasawa, A.; Tsumaya, K.; Awaji, T.; Katsuma, S.; Adachi, T.; Yamada, M.; Sugimoto, Y.; Miyazaki, S.; Tsujimoto, G. Free Fatty Acids Regulate Gut Incretin Glucagon-like Peptide-1 Secretion through GPR120 Nat. Med. 2005, 11, 90-94
22. 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
23. Elshourbagy, N. A.; Ames, R. S.; Fitzgerald, L. R.; Foley, J. J.; Chambers, J. K.; Szekeres, P. G.; Evans, N. A.; Schmidt, D. B.; Buckley, P. T.; Dytko, G. M.; Murdock, P. R.; Milligan, G.; Groarke, D. A.; Tan, K. B.; Shabon, U.; Nuthulaganti, P.; Wang, D. Y.; Wilson, S.; Bergsma, D. J.; Sarau, H. M. Receptor for the Pain Modulatory Neuropeptides FF And AF Is an Orphan G Protein-coupled Receptor J. Biol. Chem. 2000, 275, 25965-25971
24. 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
25. Payza, K.; Akar, C. A.; Yang, H. Y. Neuropeptide FF Receptors: Structure-activity Relationship And Effect of Morphine J. Pharmacol. Exp. Ther. 1993, 267, 88-94
26. Recently, RF9-mediated LH secretion was reported. Moderate bioactivity for GPR54 may also be involved in the physiological effects: Pineda, R.; Garcia-Galiano, D.; Sanchez-Garrido, M. A.; Romero, M.; Ruiz-Pino, F.; Aguilar, E.; Dijcks, F. A.; Blomenröhr, M.; Pinilla, L.; van Noort, P. I.; Tena-Sempere, M. Characterization of the Potent Gonadotropin-releasing Activity of RF9, a Selective Antagonist of RFamide-related Peptides and Neuropeptide FF Receptors: Physiological and Pharmacological Implications Endocrinology 2010, 151, 1902-1913
27. 1 Receptor Antagonists Eur. J. Pharmacol. 2002, 451, 245-256
28. Kriegsfeld, L. J.; Gibson, E. M.; Williams, W. P., III; Zhao, S.; Mason, A. O.; Bentley, G. E.; Tsutsui, K. The Roles of RFamide-related Peptide-3 in Mammalian Reproductive Function and Behaviour J. Neuroendocrinol. 2010, 22, 692-700 and the references therein.
29. Quennell, J. H.; Rizwan, M. Z.; Relf, H. L.; Anderson, G. M. Developmental and Steroidogenic Effects on the Gene Expression of RFamide Related Peptides and Their Receptor in the Rat Brain and Pituitary Gland J. Neuroendocrinol. 2010, 22, 309-316
30. Chan, Y. M.; Broder-Fingert, S.; Wong, K. M.; Seminara, S. B. Kisspeptin/Gpr54-independent Gonadotrophin-releasing Hormone Activity in Kiss1 and Gpr54 Mutant Mice J. Neuroendocrinol. 2009, 21, 1015-1023