Potent Gastrin-Releasing Peptide (GRP) Antagonists Derived from GRP(19-27) with a C-Terminal DProψ[CH2NH]Phe-NH2 and N-Terminal Aromatic Residues

Journal of Medicinal Chemistry

Volumn 37, Issue 4, 1994, Pages 439-445

  Leban, Johann J ^a   Landavazo, Antonio ^a   McDermed, John D ^a   Diliberto, Emanuel J ^b   Jansen, Marilyn ^b   Stockstill, Beth ^c   Hull, Frederick C ^c  

^a Glaxo Wellcome   (United States)

^b Burroughs Wellcome Co   (United States)

^c Division of Cell Biology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE DERIVATIVE; DEXTRO PHENYLALANINE; GASTRIN RELEASING PEPTIDE DERIVATIVE; GASTRIN RELEASING PEPTIDE[19-27]; HISTIDINE; HYDROCINNAMIC ACID; PEPTIDE HORMONE ANTAGONIST; PHENYLALANINE; PROLINE; STATINE DERIVATIVE; TRYPTOPHAN; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; AMINO TERMINAL SEQUENCE; ANIMAL CELL; ARTICLE; CARBOXY TERMINAL SEQUENCE; DRUG POTENCY; DRUG STABILITY; MITOSIS INHIBITION; MOUSE; NONHUMAN; PEPTIDE SYNTHESIS; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; GASTRIN-RELEASING PEPTIDE; MOLECULAR SEQUENCE DATA; MUTAGENICITY TESTS; OLIGOPEPTIDES; PEPTIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0028293933     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00030a002     Document Type: Article

References (32)

1. Bombesin-like Peptides in Health and Disease; Tache, Y., Melchiorri, P., Negri, L., Eds.; New York Academy of Sciences: New York, 1988; Vol. 547.
2. Lebacq-Verheyden, A. M.; Trepel, J.; Sausville, E. A.; Battey, J. F. Bombesin and gastrin-releasing peptide: neuropeptides, secretogogues, and growth factors. In Peptide Growth Factors and their Receptors II; Sporn, Roberts, Eds.; Springer-Verlag: Berlin, 1990; Vol. 2, pp 70-124.
3. Moody, T. W.; Pert, C. B.; Gazdar, A. F.; Carney, D. N.; Minna, J. D. High levels of intracellular bombesin characterize human small-cell lung carcinoma. Science 1981, 214, 1246-1248.
4. Yamaguchi, K.; Abe, K.; Kameya, T.; Adachi, I.; Taguchi, S.; Otsubo, K.; Yanaihara, N. Production and molecular size heterogeneity of immunoreactive gastrin-releasing peptide in fetal and adult lungs and primary lung tumors. Cancer Res. 1983, 43, 3932-3939.
5. Maruno, K.; Yamaguchi, K.; Abe, K.; Suzuki, M.; Saijo, N.; Mishima, Y.; Yanaihara, N.; Shimosato, Y. Immunoreactive gastrin-releasing peptide as a specific tumor marker in patients with small cell lung carcinoma. Cancer Res. 1989, 49, 629-632.
6. Cuttitta, F.; Carney, D. N.; Mulshine, J.; Moody, T. W.; Fedorko, J.; Fischler, A.; Minna, J. D. Bombesin-like peptides can function as autocrine growth factors in human small-cell lung cancer. Nature 1985, 316, 823-826.
7. Carney, D. N.; Cuttitta, F.; Moody, T. W.; Minna, J. D. Selective stimulation of small cell lung cancer clonal growth by bombesin and gastrin-releasing peptide. Cancer Res. 1987, 47, 821-825.
8. Coy, D. H.; Taylor, J. E.; Jiang, N.-Y.; Kim, S. H.; Wang, L.-H.; Huang, S.; Moreau, J.-P.; Gardner, J. D.; Jensen, R. T. Short-chain pseudopeptide bombesin receptor antagonists with enhanced binding affinities for pancreatic acinar and Swiss 3T3 cells display strong antimitotic activity. J. Biol. Chem. 1989, 264, 14691-14697.
9. Mahmoud, S.; Staley, J.; Taylor, J.; Bogden, A.; Moreau, J.-P.; Coy, D.; Avis, I.; Cuttitta, F.; Mulshine, J.L.; Moody, T. W. [Psi13,14]- Bombesin analogues inhibit growth of small cell lung cancer in vitro and in vivo. Cancer Res. 1991, 51, 1798-1802.
10. Radulovic, S.; Miller, G.; Schally, A. V. Inhibition of growth of HT-29 human colon cancer xenografts in nude mice by treatment with bombesin/gastrin releasing peptide antagonist (RC-3095). Cancer Res. 1991, 51, 6006-6009.
11. Rozengurt, E.; Sinnett-Smith, J. Bombesin stimulation of DNA synthesis and cell division in cultures of Swiss 3T3 cells. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 2936-2940.
12. Rozengurt, E. Early signals in the mitogenic response. Science 1986, 234, 161-166.
13. Narayan, S.; Guo, Y.-S.; Townsend, C. M., Jr.; Singh, P. Specific binding and growth effects of bombesin-related peptides on mouse colon cancer cells in vitro. Cancer Res. 1990, 50, 6772-6778.
14. Girard, F.; Bachelard, H.; St-Pierre, S.; Rioux, F. The contractile effect of bombesin, gastrin releasing peptide and various fragments in the rat stomach strip. Eur. J. Pharm. 1984, 102, 489-497.
15. Leban, J.J.; Kull, F.C., Jr.; Landavazo, A.; Stockstill, B.; McDermed, J. D. Development of potent gastrin-releasing peptide antagonists having a DProline-Ψ (CH2NH)Phenylalanine-amide C-terminus. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 1922-1926.
16. Merrifield, R. B. Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 1963, 85, 2149-2154.
17. Le-Nguyen, D.; Heitz, A.; Castro, B. Renin substrates. Part 2. Rapid solid phase synthesis of the ratine sequence tetradecapeptide using BOP reagent. J. Chem. Soc., Perkin Trans. 1 1987, 1915-1919.
18. Sasaki, Y.; Murphy, W. A.; Heiman, M. L.; Lance, V. A.; Coy, D. H. Solid-phase synthesis and biological properties of Ψ[CH2NH] pseudopeptide analogues of a highly potent somatostatin octapeptide. J. Med. Chem. 1987, 30, 1162-1166.
19. Mancuso, A. J.; Huang, S.-L.; Swern, D. Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide “activated” by oxalyl chloride. J. Org. Chem. 1978, 43, 2480-2482.
20. Martinez, J.; Bali, J.-P.; Rodriguez, M.; Castro, B.; Magous, R.; Laur, J.; Lignon, M.-F. Synthesis and biological activities of some pseudo-peptide analogues of tetragastrin: The importance of the peptide backbone. J. Med. Chem. 1985, 28, 1874-1879.
21. Singh, P.; Guo, Y.-S.; Kull, F. C.; Leban, J. J. A novel bombesin receptor antagonist (2258U89), potently inhibits bombesin evoked release of gastrointestinal hormones from rats and dogs, in vitro and in vivo. Regul. Pept. 1992, 40, 75-86.
22. Kim, S. H.; Taylor, J. E.; Jensen, R. T.; Coy, D. H.; Bogden, A. E.; Moreau, J.-P. C-terminal modified bombesin and litorin analogs with potent in vitro and in vivo antiproliferative activity. In Peptides: Proceedings of the Eleventh American Peptide Symposium; Rivier, J. E., Marshall, G. R., Eds.; Escom: Leiden, The Netherlands, 1990; pp 182-184.
23. Rivier, J. E.; Brown, M. R. Bombesin, bombesin analogs, and related peptides: effects on thermoregulation. Biochemistry 1978, 17, 1766-1771.
24. Camble, R.; Cotton, R.; Dutta, A. S.; Garner, A.; Hayward, C. F.; Moore, V. E.; Scholes, P. B. ICI 216140 and other potent in vivo antagonist analogs of bombesin/gastrin-releasing peptide. In Peptides: Proceedings of the Eleventh American Peptide Symposium; Rivier, J. E., Marshall, G. R., Eds.; Escom: Leiden, The Netherlands, 1990; pp 174-176.
25. Pettibone, D. J.; Totaro, J. A.; Harris, E.; Robinson, F. M. Heterogeneity of [3H] neurotensin binding: studies with dynorphin, L-156,903 and levocabastine. Brain Res. 1988, 457, 212-218.
26. Roberts, N. A.; Martin, J. A.; Kinchington, D.; Broadhurst, A. V.; Craig, J. C.; Duncan, I. B.; Galpin, S. A.; Handa, B. K.; Krohn, A.; Lambert, R. W.; Merrett, J. H.; Mills, J. S.; Parkes, K. E. B.; Redshaw, S.; Ritchie, A. J.; Taylor, D. L.; Thomas, G. I.; Machin, P. J. Rational design of peptide-based HIV proteinase inhibitors. Science 1990, 248, 358-361.
27. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 1970, 34, 595-598.
28. Sakakibara, S.; Shimonishi, Y.; Kishida, Y.; Okada, M.; Sugihara, H. Use of anhydrous hydrogen fluoride in peptide synthesis. I. Behavior of various protecting groups in anhydrous hydrogen fluoride. Bull. Chem. Soc. Jpn. 1967, 40, 2164-2167.
29. Kull, F.C., Jr.; Leban, J. J.; Landavazo, A.; Stockstill, B.; McDermed, J. D. Conveyance of partial agonism/antagonism to bombesin/gastrin releasing peptide analogs on Swiss 3T3 cells by a carboxylterminal leucine insertion. J. Biol. Chem. 1992, 267, 21132-21138.
30. Zachary, I.; Rozengurt, E. High-affinity receptors for peptides of the bombesin family in Swiss 3T3 cells. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 7616-7620.
31. Jensen, R. T.; Moody, T. W.; Pert, C.; Rivier, J. E.; Gardner, J. D. Interaction of bombesin and litorin with specific membrane receptors on pancreatic acinar cells. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 6139-6143.
32. Naldini, L.; Cirillo, D.; Moody, T. W.; Comoglio, P. M.; Schlessinger, J.; Kris, R. Solubilization of the receptor for the neuropeptide gastrin-releasing peptide (bombesin) with functional ligand binding properties. Biochemistry 1990, 29, 5153-5160.