Synthesis and binding potencies of cyclohexapeptide somatostatin analogs containing naphthylalanine and arylalkyl peptoid residues

Journal of Peptide Science

Volumn 5, Issue 3, 1999, Pages 113-130

  Tran, Thuy Anh ^a   Mattern, Ralph Heiko ^a   Morgan, Barry A ^b   Taylor, John E ^b   Goodman, Murray ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Biomeasure Inc   (United States)

Author keywords

Binding activities; Hsst receptors; Peptoids; Somatostatin analogs; Synthesis

Indexed keywords

ALANINE DERIVATIVE; CYCLO(PROLYLPHENYLALANYL DEXTRO TRYPTOPHYLLYSYLTHREONYLPHENYLALANYL); CYCLOPEPTIDE; HEXAPEPTIDE; SOMATOSTATIN DERIVATIVE; SOMATOSTATIN RECEPTOR; 1 NAPHTHYLALANINE; 1-NAPHTHYLALANINE; ALANINE; CYCLO(PRO PHE TRP LYS THR PHE); CYCLO(PRO-PHE-TRP-LYS-THR-PHE); DRUG DERIVATIVE; PEPTIDE FRAGMENT; PEPTOID; RECOMBINANT PROTEIN; SOMATOSTATIN;

ARTICLE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION; AMINO ACID SEQUENCE; ANIMAL; BINDING SITE; CHEMISTRY; HUMAN; METABOLISM; SYNTHESIS;

ALANINE; AMINO ACID SEQUENCE; ANIMALS; BINDING SITES; HUMANS; PEPTIDE FRAGMENTS; PEPTIDES, CYCLIC; PEPTOIDS; RECEPTORS, SOMATOSTATIN; RECOMBINANT PROTEINS; SOMATOSTATIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032588027     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1387(199903)5:3<113::AID-PSC176>3.0.CO;2-N     Document Type: Article

References (25)

1. (a) P. Brazeau, W. Vale, R. Burgus, N. Ling, M. Bucher, J. Rivier and R. Guillemin (1973). Hypothalamic polypeptide that inhibits the secretion of the immunoreactive growth hormone. Science 179, 77-79.
2. (b) D.J. Koerker, L.A. Harker and C.J. Goodner (1975). Effects of somatostatin on hemostasis in baboons. Engl. J. Med. 96, 749-754.
3. (c) J.E. Gerich, R. Lovinger and G.M. Grodsky (1975). Glucagon and insulin release from the perfused rat pancreas in response to arginine, isoproterenol and theophylline: evidence for a preferential effect on glucagon secretion. Endocrinology 96, 749-754.
4. (a) R. Hall, A.V. Schally, D. Evered, A. J. Kastin, C.H. Mortimer, W.M.G. Tunbridge, G.M. Besser, D.H. Coy, D.J. Goldie, A.S. McNeilly, C. Phenekos and D. Weightmen (1973). Action of growth-hormone-release inhibitory in healthy men and acromegaly. Lancet 2, 581.
5. (b) S.W.J. Lamberts, E.P. Krenning and J.C. Reubi (1991). The role of somatostatin and its analogs in diagnosis and treatment of tumors. Endocrine Rev. 12, 450-482.
6. G.I. Bell and T. Reisine (1993). Molecular biology of somatostatin receptors. Trends Neurosci. 16, 34-38.
7. (a) D. Hoyer, G.I. Bell, M. Berelowitz, J. Epelbaum, W. Feniuk, P.P.A. Humphrey, A.-M. O'Carroll, Y.C. Patel, A. Schonbrunn, J.E. Taylor and T. Reisine (1995). Classification and nomenclature of somatostatin receptors Trends Pharmacol. Sci. 16, 86-88.
8. (b) K. Raynor, W. Murphy, D. Coy, J. Taylor, J.-P. Moreau, K. Yasuda, G.I. Bell and T. Reisine (1993). Cloned somatostatin receptors - identification of subtype-selective peptides and demonstration of high affinity binding of linear peptides. Mol. Pharmacol. 43, 838-844.
9. (c) K. Raynor, A.-M. O'Carroll, H. Kong, K. Yasuda, L. Mahan, G.I. Bell and T. Reisine (1993). Characterization of cloned somatostatin receptors SSTR4 and SSTR5. Mol. Pharmacol. 44, 385-392.
10. (a) L. Buscail, N. Delesque, J.-P. Esteve, N. Saint-Laurent, H. Prats, P. Clerc, D. Robberecht, G.I. Bell, C. Liebow, A.V. Schally, N. Vaysse and C. Susini (1994). Stimulation of tyrosine phosphatase and inhibition of cell proliferation by somatostatin analogues - mediation by human somatostatin receptor subtypes SSTR1 and SSTR2. Proc. Natl. Acad. Sci. USA 91, 2315-2319.
11. (b) L. Buscail, J.-P. Esteve, N. Saint-Laurent, V. Bertrand, T. Reisine, A.-M. O'Carroll, G.I. Bell, A.V. Schally, N. Vaysse and C. Susini (1995). Inhibition of cell proliferation by the somatostatin analogue RC-160 is mediated by somatostatin receptor subtypes SSTR2 and SSTR5 through different mechanisms. Proc. Natl. Acad. Sci. USA 92, 1580-1584.
12. D.F. Veber, R.M. Freidinger, D.S. Perlow, W.J. Jr. Palaveda, F.W. Holly, R.G. Strachan, R.F. Nutt, B.J. Arison, C. Homnick, W.C. Randall, M.S. Glitzer, R. Saperstein and R. Hirschmann (1981). A potent cyclic hexapeptide analogue of somatostatin. Nature 292, 55-58.
13. D.F. Veber in: Peptides, Synthesis, Structure and Function. Proceedings of the Seventh American Peptides Symposium. D.H. Rich and V.J. Gross Eds, p. 345-348. Pierce Chemical Co., Rockford, IL, 1983.
14. D.F. Veber. Design and discovery in the development of peptide analogs, in: Peptides: Chemistry and Biology. Proceedings of the Twelfth American Peptide Symposium. J.A. Smith and J.E. Rivier Eds, p. 3-14, ESCOM, Leiden, 1992.
15. R.M. Freidinger, D.S. Perlow, W.C. Randall, R. Saperstein, B.H. Arison and D.F. Veber (1984). Conformational modifications of cyclic hexapeptide somatostatin analogs. Int. J. Peptide Protein Res. 23, 142-150.
16. (a) Z. Huang, Y.-B. He, K. Raynor, M. Tallent, T. Reisine and M. Goodman (1992). Main chain and side chain chiral methylated somatostatin analogs: Syntheses and conformatlonal analyses. J. Am. Chem. Soc. 114, 9390-9401.
17. (b) Y.-B. He, Z. Huang, K. Raynor, T. Reisine and M. Goodman (1993). Conformations of somatostatin related cyclic hexapeptides incorporating specific α-methylated and β-methylated residues. J. Am. Chem. Soc. 115, 8066-8072.
18. (a) T.-A. Tran, R.-H. Mattern, M. Afargan, O. Amitay, O. Ziv, B.A. Morgan, J.E. Taylor, D. Hoyer and M. Goodman (1998). Design, synthesis, and biological activities of potent and selective somatostatin analogs incorporating novel peptoid residues. J. Med. Chem. 41, 2679-2685.
19. (b) R.-H. Mattern, T.-A. Tran and M. Goodman (1998). Conformational analysis of somatostatin related cyclic hexapeptides containing peptoid residues. J. Med. Chem. 41, 2686-2692.
20. R.-H. Mattern, T-.A. Tran and M. Goodman (1999). Conformational analysis of cyclic hexapeptides related to somatostatin containing arylalkyl peptoid residues and naphthyl alanine residues. J. Peptide Sci., in press.
21. S.M. Miller, R.J. Simon, S. Ng, R.N. Zuckerman, J.M. Kerr and W.H. Moos (1995). Comparison of the proteolytic susceptibilities of homologous L-amino acid, DD-amino acid, and N-substituted glycine peptide and peptoid oligomers. Drug Develop. Res. 35, 20-32.
22. (a) A.M. Mouna, C. Nguyen, I. Rage and J. Xie (1994). Preparation of Boc-N-alkyl glycines for peptoid synthesis. Syn. Commun. 24, 2429-2435.
23. (b) R.J. Simon, R.S. Kania, R.N. Zuckermann, V.D. Huebner, D.A. Jewell, S. Banville, S. Ng, L. Wang, S. Rosenberg, C. K. Marlowe, D.C. Spellmeyer, R. Tan, A.D. Frankel, D.V. Santi, F.E. Cohen and P.A. Bartlett (1992). Peptoids - a modular approach to drug discovery. Proc. Natl. Acad. Sci. USA 89, 9367-9371.
24. J.R. Spencer, N.G.J. Delaet, A. Toy-Palmer, V.V. Antonenko and M. Goodman (1993). Unusual peptide bond cleavage reactions during acidolytic deprotection reactions. J. Org. Chem. 58, 1635-1638.
25. F.M. Ausabel, R. Brent, R.E. Kingston, D.D. Moore, J.G. Seidman, J.A. Smith and K. Struhl in: Current Protocols in Molecular Biology, John Wiley & Sons, New York, 1987.