Identification of high-potency neuropeptide Y analogues through systematic lactamization

Journal of Medicinal Chemistry

Volumn 40, Issue 2, 1997, Pages 210-215

  Kirby, Dean A ^a   Britton, Karen T ^b   Aubert, Michel L ^c   Rivier, Jean E ^a  

^a SALK INSTITUTE FOR BIOLOGICAL STUDIES   (United States)

^b VA SAN DIEGO HEALTHCARE SYSTEM   (United States)

^c UNIVERSITY OF GENEVA MEDICAL SCHOOL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIC AMP; NEUROPEPTIDE Y; NEUROPEPTIDE Y DERIVATIVE; NEUROPEPTIDE Y1 RECEPTOR; NEUROPEPTIDE Y2 RECEPTOR; NORADRENALIN;

ARTICLE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NEUROBLASTOMA CELL; RECEPTOR BINDING;

AMINO ACID SEQUENCE; CELL MEMBRANE; HUMANS; KINETICS; LACTAMS; MOLECULAR SEQUENCE DATA; NEUROBLASTOMA; NEUROPEPTIDE Y; RECEPTORS, NEUROPEPTIDE Y;

EID: 0031013481     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960593h     Document Type: Article

References (53)

1. Gray, T. S.; Morley, J. E. Neuropeptide Y: anatomical distribution and possible function in mammalian nervous system. Life Sci. 1986, 38, 389-401.
2. Stanley, B. G.; Kyrkouli, S. E.; Lampert, S.; Leibowitz, S. F. Neuropeptide Y chronically injected into the hypothalamus: A powerful neurochemical inducer of hyperphagia and obesity. Peptides 1986, 7, 1189-1192.
3. Hua, X.-Y.; Boublik, J. H.; Spicer, M. A.; Rivier, J. E.; Brown, M. R.; Yaksh, T. L. The antinociceptive effects of spinally administered neuropeptide Y in the rat: systematic studies on structure activity relationship. J. Pharmacol. Exp. Ther. 1990, 258, 243-248.
4. Heilig, M.; McLeod, S.; Koob, G.; Britton, K. Anxiolytic-like effects of neuropeptide Y (NPY), but not other peptides in an operant conflict test. Reg. Pept. 1992, 41, 61-69.
5. Catzeflis, C.; Pierroz, D. D.; Rohner-Jeanrenaud, F.; Rivier, J. E.; Sizonenko, P. C.; Aubert, M. L. Neuropeptide Y administered chronically into the lateral ventricle profoundly inhibits both the gonadotropic and the somatotropic axis in intact adult female rats. Endocrinology 1993, 132, 224-234.
6. Walker, F.; Burgess, A. W. Reconstitution of the high affinity epidermal growth factor receptor on cell-free membranes after transmodulation by platelet-derived growth factor. J. Biol. Chem. 1991, 266, 2746-2752.
7. Wahlestedt, C.; Edvinsson, L.; Ekblad, E.; Hakanson, R. Neuropeptide Y potentiates noradrenaline-evoked vasoconstriction: Mode of action. J. Pharmacol. Exp. Ther. 1985, 234, 735-741.
8. Allen, J.; Novotny, J.; Martin, J.; Heinrich, G. Molecular structure of mammalian neuropeptide Y: Analysis by molecular cloning and computer-aided comparison with crystal structure of avian homologue. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 2532-2536.
9. Mierke, D. F.; Dürr, H.; Kessler, H.; Jung, G. Neuropeptide Y. Optimized solid-phase synthesis and conformational analysis in tribluoroethanol. Eur. J. Biochem. 1992, 206, 39-48.
10. 1H-NMR spectroscopy. Biopolymers 1995, 35, 583-593.
11. Wettstein, J. G.; Earley, B.; Junien, J. L. Central nervous system pharmacology of neuropeptide Y. Pharmacol. Ther. 1995, 65, 397-414.
12. 2 receptors for neuropeptide Y. Fed. Eur. Biochem. Soc. 1989, 245 (No. 1,2), 209-214.
13. 1 mRNA in forebrain areas of the rat central nervous systems. Eur. J. Neurosci. 1993, 5, 1622-1637.
14. Herzog, H.; Hort, Y. J.; Ball, J. J.; Hayes, G.; Shine, J.; Selbie, L. A. Cloned human neuropeptide Y receptor couples to two different second messenger systems. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 5794-5798.
15. Gehlert, D. R. Subtypes of receptors for neuropeptide Y: Implications for the targeting of therapeutics. Life Sci. 1994, 55, 551-562.
16. Wahlestedt, C.; Regunathan, S.; Reis, D. J. Identification of cultured cells selectively expressing Y1-type, Y2-type or Y3-type receptors for neuropeptide Y/peptide YY. Life Sci. 1992, 50, P17-P112.
17. 3 receptors. Eur. J. Pharmacol. 1995, 278, R3-R5.
18. Bard, J. A.; Walker, M. W.; Branchek, T. A.; Weinshank, R. L. Cloning and functional expression of a human Y4 subtype receptor for pancreatic polypeptide, neuropeptide Y, and peptide YY. J. Biol. Chem. 1995, 270, 26762-26765.
19. Gerald, C.; Walker, M. W.; Criscione, L.; Gustafson, E. L.; Batzl-Hartmann, C.; Smith, K. E.; Vaysse, P.; Durkin, M. M.; Laz, T. M.; Linemeyer, D. L.; Schaffhauser, A. O.; Whitebread, S.; Hofbauer, K. G.; Taber, R. I.; Branchek, T. A.; Weinshank, R. L. A receptor subtype involved in neuropeptide-Y-induced food intake. Nature 1996, 382, 168-171.
20. Lundell, I.; Blomqvist, A. G.; Berglund, M. M.; Schober, D. A.; Johnson, D.; Statnick, M. A.; Gadski, R. A.; Gehlert, D. R.; Larhammar, D. Cloning of a human receptor of the NPY receptor family with high affinity for pancreatic polypeptide and peptide YY. J. Biol. Chem. 1995, 270, 29123-29128.
21. Lundell, I.; Statnick, M. A.; Johnson, D.; Schober, D. A.; Starback, P.; Gehlert, D. R.; Larhammar, D. The cloned rat pancreatic polypeptide receptor exhibits profound differences to the orthologous human receptor. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 5111-5115.
22. Yan, H.; Yang, J.; Marasco, J.; Yamaguchi, K.; Brenner, S.; Collins, F.; Karbon, W. Cloning and functional expression of cDNAs encoding human and rat pancreatic polypeptide receptors. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 4661-4665.
23. Rose, P. M.; Fernandes, P.; Lynch, J. S.; Frazier, S. T.; Fisher, S. M.; Kodukula, K.; Kienzle, B.; Seethala, R. Cloning and functional expression of a cDNA encoding a human type 2 neuropeptide Y receptor. J. Biol. Chem. 1995, 270, 22661-22664.
24. Kirby, D. A.; Feinstein, R. D.; Koerber, S. C.; Brown, M. R.; Rivier, J. E. Structure-activity relationships of conformationally restricted deletion analogs of Neuropeptide Y. In Peptides: Chemistry and Biology; Smith, J., Rivier, J., Eds.; ESCOM Science Publishers, B.V.: Leiden, The Netherlands, 1992; pp 480-481.
25. 2 receptor. Eur. J. Biochem. 1992, 206, 957-964.
26. 2+ channel currents in human neuroblastoma (SH-SY5Y) cells by neuropeptide Y and a novel cyclic neuropeptide Y analogue. Neuropharmacology 1995, 34, 1507-1514.
27. 1 receptor subclass. J. Med. Chem. 1995, 38, 4579-4586.
28. Krstenansky, J. L.; Owen, T. J.; Buck, S. H.; Hagaman, K.; McLean, L. R. Centrally truncated and stablilized porcine neuropeptide Y analogs: Design, synthesis, and mouse brain receptor binding. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 4377-4381.
29. 2 Receptor. J. Med. Chem. 1994, 37, 2242-2248.
30. 1 receptor antagonist: BIBP3226. Eur. J. Pharm. 1994, 271, R11-R13.
31. Serradeil-Le Gal, C.; Valette, G.; Rouby, P.-E.; Pellet, A.; Oury-Donat, F.; Brossard, G.; Lespy, L.; Marty, E.; Neliat, G.; de Cointet, P.; Maffrand, J.-P.; Le Fur, G. SR120819A, an orally-active and selective neuropeptide Y Y1 receptor antagonist. FEBS Lett. 1995, 362, 192-196.
32. Felix, A. M.; Wang, C.-T.; Campbell, R. M.; Toome, V.; Fry, D. C.; Madison, V. S. Biologically active cyclic (lactam) analogs of growth hormone-releasing factor: Effect of ring size and location on conformation and biological activity. In Peptides: Chemistry and Biology; Smith, J. A., Rivier, J. E., Eds.; ESCOM Science Publishers, B.V.: Leiden, The Netherlands, 1992; pp 77-79.
33. Gulyas, J.; Rivier, C.; Perrin, M.; Koerber, S. C.; Sutton, S.; Corrigan, A.; Lahrichi, S. L.; Craig, A. G.; Vale, W.; Rivier, J. Potent, structurally constrained agonists and competitive antagonists of corticotropin-releasing factor. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 10575-10579.
34. 1. J. Med. Chem. 1996, 39, 1136-1141.
35. Boublik, J. H.; Scott, N. A.; Brown, M. R.; Rivier, J. E. Synthesis and hypertensive activity of neuropeptide Y fragments and analogs with modified N- or C-termini or D-substitutions. J. Med. Chem. 1989, 32, 597-601.
36. Beck-Sickinger, A.; Jung, G.; Gaida, W.; Koppen, H.; Lang, R.; Schnorrenberg, G. Highly potent and small neuropeptide Y agonist obtained by linking NPY 1-4 via spacer to alpha-helical NPY 25-36. FEBS Lett. 1989, 244, 119-122.
37. Sautel, M.; Martinez, R.; Munoz, M.; Peitsch, M. C.; Beck-Sickinger, A. G.; Walker, P. Role of a hydrophobic pocket of the human Y1 neuropeptide Y receptor in ligand binding. Mol. Cell. Endocrinol. 1995, 112, 215-222.
38. 1 receptor. Mol. Pharmacol. 1996, 50, 285-292.
39. Strader, C. D.; Fong, T. M.; Graziano, M. P.; Tota, M. R. The family of G-protein-coupled receptors. FASEB J. 1995, 9, 745-754.
40. Abens, J.; Unden, A.; Andell, S.; Tam, J. P.; Bartfai, T. Synthetic fragments and analogs of NPY are ligands at NPY receptors in the rat cerebral cortex. In Neuropeptide Y; Mutt, V., Hökfelt, T., Fuxe, K., Lundberg, J. M., Eds.; Raven Press: New York, 1989; pp 137-142.
41. Forest, M.; Martel, J. C.; St.-Pierre, S.; Quirion, R.; Fournier, A. Structural study of the N-terminal segment of neuropeptide tyrosine. J. Med. Chem. 1990, 33, 1615-1619.
42. 1 receptor agonist. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 182-186.
43. 2 radioligands. J. Pharmacol. Exp. Ther. 1995, 272, 673-680.
44. Jorgensen, J. C.; Fuhlendorff, J.; Schwartz, T. W. Structure-function studies on neuropeptide Y and pancreatic polypeptide - evidence for two PP-fold receptors in vas deferens. Eur. J. Pharmacol. 1990, 186, 105-114.
45. Krstenansky, J. L.; Owen, T. J.; Payne, M. H.; Shatzer, S. A.; Buck, S. H. C-terminal modifications of neuropeptide Y and its analogs leading to selectivity for the mouse brain receptor over the porcine spleen receptor. Neuropeptides 1990, 17, 117-120.
46. Michel, M. C. Receptors for neuropeptide Y: Multiple subtypes and multiple second messengers. TIPS 1991, 12, 389-394.
47. Walker, P.; Munoz, M.; Martinez, R.; Peitsch, M. C. Acidic residues in extracellular loops of the human Y1 neuropeptide Y receptor are essential for ligand binding. J. Biol. Chem. 1994, 269, 2863-2869.
48. 1-type receptor. J. Med. Chem. 1995, 38, 1150-1157.
49. 34]NPY-(31-36)}: A specific NPY Y-1 receptor antagonist. J. Med. Chem. 1996, 39, 811-813.
50. Ihara, M.; Kanatani, A.; Ishihara, A.; Asahi, S.; Tanaka, T.; Ozaki, S. Potent neuropeptide Y Y1 receptor antagonist WP-4: Blockade of NPY-induced food intake. Presented at New Discoveries Within the Pancreatic Polypeptide Family: From Molecules to Medicine, The Physiologist, Newport Beach, CA, Nov 8-11, 1995; 4.32.
51. Leff, P. The two-state model of receptor activation. TIPS 1995, 16, 89-97.
52. Heilig, M.; McLeod, S.; Brot, M.; Heinrichs, S. C.; Menzaghi, F.; Koob, G. F.; Britton, K. T. Anxiolytic-like action of neuropeptide Y: Mediation by Y1 receptors in amygdala, and dissociation from food intake effects. Neuropsychopharmacology 1993, 8, 357-363.
53. 3H]BIBP3226. NeuroReport 1996, 7, 901-904.