Chimeric strategies for the rational design of bioactive analogs of small peptide hormones

FASEB Journal

Volumn 11, Issue 7, 1997, Pages 582-590

  Howl, John ^a   Langel, Ülo ^b   Hawtin, Stuart R ^a   Valkna, Andres ^b   Yarwood, Nicola J ^a   Saar, Külliki ^b   Wheatley, Mark ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Antagonist; Bradykinin; Galanin; Mastoparan; Vasopressin

Indexed keywords

ARGIPRESSIN DERIVATIVE; BRADYKININ B2 RECEPTOR; BRADYKININ DERIVATIVE; CHIMERIC PROTEIN; GALANIN DERIVATIVE; MASTOPARAN; PEPTIDE HORMONE; SYNTHETIC PEPTIDE;

AMINO TERMINAL SEQUENCE; ANIMAL TISSUE; ARTICLE; CATTLE; CHIMERA; CONTROLLED STUDY; HORMONE RECEPTOR INTERACTION; HORMONE SYNTHESIS; KIDNEY MEDULLA; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

ANIMALIA; BOS TAURUS; BOVINAE;

EID: 0030989997     PISSN: 08926638     EISSN: None     Source Type: Journal    
DOI: 10.1096/fasebj.11.7.9212082     Document Type: Article

References (54)

1. Manning, M., Bankowski, K., and Sawyer, W. H. (1987) Selective agonists and antagonists of vasopressin. In Vasopressin (Jard, S., and Jamison, R., eds) pp. 335-368, Plenum, New York
2. 2 receptor characterization. Trends Pharmacol. Sci. 11, 156-161
3. Stewart, J. M. (1995) Bradykinin antagonists: Developments and applications. Biopolymers 37, 143-155
4. László, F. A., László, F., Jr., and DeWeid, D. (1991) Pharmacology and clinical perspectives of vasopressin antagonists. Pharmacol. Rev. 43, 73-108
5. Margolius, H. S. (1989) Tissue kallikreins and kinins: Regulation and roles in hypertensive and diabetic diseases. Annu. Rev. Pharmacol. Toxicol. 29, 343-364
6. Sharma, J. N. (1993) Therapeutic prospects of bradykinin receptor antagonists. Gen. Pharmacol. 24, 267-274
7. Jard, S., Barberis, C., Audigier, S., and Tribollet, E. (1987) Neurohypophysial hormone receptor systems in brain and periphery. Prog. Brain. Res. 72, 173-187
8. 1a vasopressin receptors. Gen. Pharmacol. 26, 1143-1152
9. Regoli, D., Jukic, D., Gobeil, F., and Rhaleb, N.-E. (1993) Receptors for bradykinin and related kinins: A critical analysis. Can. J. Physiol. Pharmacol. 71, 556-567
10. 2 subtypes. Life Sci. 55, 735-749
11. Howl, J., Yarwood, N. J., Davies, A. R. L., and Wheatley, M. (1996) Renal bradykinin and vasopressin receptors: Ligand selectivity and classification. Kidney Int. 50, 586-592
12. Bartfai, T., Hökfelt, T., and Langel, Ü. (1993) Galanin - a neuroendocrine peptide. Crit. Rev. Neurobiol. 7, 229-274
13. 1 antagonists in dimethyl sulfoxide solution derived from two-dimensional NMR spectroscopy and molecular dynamics simulation. Eur. J. Biochem. 201, 355-371
14. Otter, A., Bigler, P., Stewart, J. M., and Kotovych, G. (1993) A proton magnetic resonance study of two synthetic agonist-antagonist pairs of bradykinin analogs. Biopolymers 33, 769-780
15. Rose, J. P., Wu, C.-K., Hsiao, C.-D., Breslow, E., and Wang, B.-C. (1996) Crystal structure of the neurophysin-oxytocin complex. Nature Struct. Biol. 3, 163-169
16. Sejbal, J., Cann, J. R., Stewart, J. M., Gera, L., and Kotovych, G. (1996) A NMR, CD, molecular dynamics, and fluorometric study of the conformation of the bradykinin antagonist B-9340 in water and in aqueous micellar solutions. J. Med. Chem. 39, 1281-1292
17. Cann, J. R., Liu, X., Stewart, J. M., Gera, L., and Kotovych, G. (1994) A CD and NMR study of multiple bradykinin conformations in aqueous trifluoroethanol solutions. Biopolymers 34, 869-878
18. Kyle, D. J., Chakravarty, S., Sinsko, J. C., and Stormann, T. M. (1994) A proposed model of bradykinin bound to the rat B2 receptor and its utility for drug design. J. Med. Chem. 37, 1347-1354
19. Mouillac, B., Chini, B., Balestre, M. N., Elands, J., Trumppkallmeyer, S., Hoflack, J., Hibert, M., Jard, S., and Barberis, C. (1995) The binding-site of neuropeptide vasopressin V1a receptor. Evidence for a major localization within transmembrane domains. J. Biol. Chem. 270, 25711-25777
20. Juréus, A., and Langel, Ü. (1996) Galanin and galanin antagonists. Acta. Chim. Slovenica 43, 51-60
21. Valkna, A., Laidmäe, E., Karelson, E., Zilmer, M., Juréus, A., and Langel, Ü. (1995) Effects of chimeric galanin receptor ligands on basal adenylate cyclase activity in rat ventral hippocampal membranes. Protein Pept. Lett. 2, 267-274
22. Langel, Ü., Land, T., and Bartfai, T. (1992) Design of chimeric peptide ligands to galanin receptors and substance P receptors. Int. J. Pept. Protein. Res. 39, 516-522
23. 1a vasopressin receptors: Selective biotinylated probes. Methods Neurosci. 13, 281-296
24. Howl, J., Ismail, T., Strain, A. J., Kirk, C. J., Anderson, D., and Wheatley, M. (1991) Characterization of the human liver vasopressin receptor. Biochem. J. 276, 189-195
25. 1a vasopressin receptors. Mol. Cell. Endocrinol. 77, 123-131
26. 50) of an enzymic reaction. Biochem. Pharmacol. 22, 3099-3108
27. 2+ in a neural cell line. EMBO J. 6, 49-54
28. 1a vasopressin receptor. Eur. J. Biochem. 213, 711-719
29. Kirk, C.J., Guillon, G., Balestere, M.-N., and Jard, S. (1986) Stimulation, by vasopressin and other agonists, of inositol-lipid breakdown and inositol phosphate accumulation in WRK 1 cells. Biochem. J. 240, 197-204
30. Gitelman, H. J., Klapper, D. G., Alderman, F. R., and Blythe, W. B. (1980) Bovine storage forms of arginine vasopressin with natriuretic activity. Science 207, 893-896
31. Callahan, J. F., Ashton-Shue, D., Bryan, H. G., Bryan, W. M., Heckman, G. D., Kinter, L. B., McDonald, J. E., Moore, M. L., Schmidt, D. B., Silvestri, J. S., Stassen, F. L., Sulat, L., Yim, N. C. F., and Huffman, W. F. (1989) Structure-activity relationships of novel vasopressin antagonists containing C-terminal diaminoalkanes and (aminoalkyl)guanidines. J. Med. Chem. 32, 391-396
32. 1-receptor) responses to arginine-vasopressin. J. Med. Chem. 35, 382-388
33. Manning, M., Przybylski, J. P., Olma, A., Klis, W. A., Kruszynski, M., Wo, N. C., Pelton, G. H., and Sawyer, W. H. (1987) No requirement of cyclic conformation of anatagonists in binding to vasopressin receptors. Nature (London) 329, 839-840
34. 2 agonists: Potential radioiodinated ligands for vasopressin receptors. In Peptides 1990 (Giralt, E., and Andreau, D., eds) pp. 665-667, ESCOM, Leiden, The Netherlands
35. 1a vasopressin receptor binding site with pyroglutamate-substituted linear antagonists. Neuropeptides 30, 73-79
36. Regoli, D., and Barabe, J. (1980) Pharmacology of bradykinin and related kinins. Pharmacol. Rev. 32, 1-46
37. Manning, M., and Sawyer, W. H. (1984) Design and uses of selective agonistic and antagonistic analogs of the neuropeptides oxytocin and vasopressin. Trends Neurosci. 7, 6-9
38. Acher, R. (1993) Neurohypophysial peptide hormone systems: processing machinery, hydroosmotic regulation, adaptation and evolution. Regul. Pept. 45, 1-13
39. Raynor, R. L., Zheng, B., and Kuo, J. F. (1991) Membrane interactions of amphiphilic polypeptides mastoparan, mellitin, polymyxin B, and cardiotoxin. J. Biol. Chem. 266, 2753-2758
40. Mousli, M., Bueb, J.-L., Bronner, C., Rouot, B., and Landry, Y. (1990) G protein activation: a receptor-independent mode of action for cationic amphiphilic neuropeptides and venom peptides. Trends Pharmacol. Sci. 11, 358-362
41. Jones, P. M., Mann, F. M., Persaud, S. J., and Wheeler-Jones, C. P. D. (1993) Mastoparan stimulates insulin secretion from pancreatic β-cells by effects at a late stage in the secretory pathway. Mol. Cell. Endocrinol. 94, 97-103
42. +-ATPase and reverses its inhibition by oubain. Regul. Pept. 62, 47-52
43. Östensson, C.-G., Zaitsev, S., Berggren, P.-O., Efendic, S., Langel, Ü., and Bartfai, T. (1997) Galparan, a powerful insulin releasing chimeric peptide acting at a novel site. Endocrinology In press
44. Mezna, M., Langel, Ü., Hällbrink, M., Wheatley, M., Michelangeli, F., and Howl, J. (1997) Calcium-mobilizing actions of chimeric hormone-mastoparan peptides. Biochem. Soc. Trans. 25, 450S
45. Wei, C.-M., Kim, C. H., Miller, V. M., and Burnett, J. C., Jr. (1993) Vasonatrin peptide: A unique synthetic natriuretic and vasorelaxing peptide. J. Clin. Invest. 92, 2048-2052
46. Wiegandt Long, D. L., Ma, W., and Spatola, A. F. (1996) Homooligomeric and hetro-oligomeric multifunctional peptide analogs. In Peptides: Chemistry, Structure and Biology (Kaumaya, P. T. P., and Hodges, R. S., eds) pp. 595-596, Mayflower Scientific Ltd, Kingswinford
47. Conn, P. M., Rogers, D. C., Stewart, J. M., Niedel, J., and Sheffield, T. (1982) Conversion of a gonadotropin-releasing hormone antagonist to an agonist. Nature (London) 296, 653-655
48. Cheronis, J. C., Whalley, E. T., Nguyen, K. T., Eubanks, S. R., Allen, L. G., Duggan, M. J., Loy, S. D., Bonham, K. A., and Blodgett, J. K. (1992) A new class of bradykinin antagonists: Synthesis and in vitro activity bissuccinimidylalkane peptide dimers. J. Med. Chem. 35, 1563-1572
49. 2 antagonist activity. J. Med. Chem. 37, 348-355
50. Howl, J., and Wheatley, M. (1996) Molecular recognition of peptide and non-peptide ligands by the extracellular domains of neurohypophysial hormone receptors. Biochem. J. 317, 577-582
51. 2 bradykinin receptor decreases affinity for bradykinin. Biochem. Biophys. Res. Commun. 201, 523-530
52. Chini, B., Mouillac, B., Ala, Y., Balestre, M.-N., Trumpp-Kallmeyer, S., Hoflack, J., Elands, J., Hibert, M., Manning, M., Jard, S., and Barberis, C. (1995) Tyr115 is the key residue for determining agonist selectivity in the Via vasopressin receptor. EMBO J. 14, 2176-2182
53. 2, vasopressin receptors. FEBS Lett. 362, 19-23
54. 1a vasopressin receptors: Visualization by a biotinylated ligand. Neuroendocrinology 62, 634-639