Side Chain Conformations of Somatostatin Analogs when Bound to Receptors

  • Ruth F. Nutt
  • C. Dylion Colton
  • Richard Saperstein
  • Daniel F. Veber
Part of the Serono Symposia, USA book series (SERONOSYMP)


Conformationally based design has resulted in greatly simplified constrained analogs of somatostatin which show a high degree of metabolic stability and improved duration of action.


Upfield Shift Lysine Side Chain Side Chain Conformation Cyclic Hexapeptide Pept Protein 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Veber DF, Saperstein R, Nutt RF, et al. A super active cyclic hexapeptide analog of somatostatin. Life Sci 1984; 34: 1371.PubMedCrossRefGoogle Scholar
  2. 2.
    Bauer W, Briner U, Doepfner W, et al. SMS 201-995: a very potent and selective octapeptide analogue of somatostatin with prolonged action. Life Sci 1982; 31: 1133.PubMedCrossRefGoogle Scholar
  3. 3.
    Vale W, Rivier J, Ling N, Brown M. Metabolism 1978; 27 (suppl 1): 1391.PubMedCrossRefGoogle Scholar
  4. 4.
    Cyclo(Asn-Phe-Phe-D-Trp-Lys-Thr-Phe-Gaba) CGP-15425.Google Scholar
  5. 5.
    Veber DF. Design of a highly active cyclic hexapeptide analog of somatostatin. In: Rich DH, Gross E, eds. Peptides: synthesisstructure—function. Proceedings of the 7th American Peptide Symposium, 1981: 685.Google Scholar
  6. 6.
    Arison BH, Hirschmann R, Veber DF. Inferences about the conformation of somatostatin at a biologic receptor based on NMR studies. Bio-organic Chem 1978; 7: 447.Google Scholar
  7. 7.
    Freidinger RM, Perlow DS, Randall WC, Saperstein R, Arison BH, Veber DF. Conformational modification of cyclic hexapeptide somatostatin analogs. Int J Pept Protein Res 1984; 23: 142.PubMedCrossRefGoogle Scholar
  8. 8.
    Momany FA, Bowers CY, Reynolds GA, Chang D, Hong A, Newlander R. Design, synthesis, and biological activity of peptides which release growth hormone in vitro. Endocrinology 1981; 108: 31.PubMedCrossRefGoogle Scholar
  9. 9.
    Veber DF, Holly FW, Paleveda WJ Jr, et al. Conformationally restricted bicyclic analogs of somatostatin. Proc Natl Acad Sci USA 1978; 75: 2636 - 40.PubMedCrossRefGoogle Scholar
  10. 10.
    Veber DF, Freidinger RM, Perlow DP, et al. A potent cyclic hexapeptide analog of somatostatin. Nature 1981; 292: 55.PubMedCrossRefGoogle Scholar
  11. 11.
    Veber DF, Randall WC, Nutt RF, et al. Circular dichroism aids interpretation of structure-activity relationships of somatostatin analogs. In: Blaha K, Malon P, eds. Proceedings of the 17th European Peptide Symposium, Peptides 1982, 1982: 789.Google Scholar
  12. 12.
    Nutt RF, Veber DF, Curley PE, Saperstein R, Hirschmann R. Somatostatin analogs which define the role of the lysine-9 amino group. Int J Pept Protein Res 1983; 21: 66.PubMedCrossRefGoogle Scholar
  13. 13.
    Freidinger RM, Veber DF. Design of novel cyclic hexapeptide somatostatin analogs from a model of the bioactive conformation. In: Conformationally directed drug design. ACS Symposium Series 251, Am Chem Soc, Washington, DC, 1984.Google Scholar
  14. 14.
    Nutt RF, Saperstein R, Veber DF. Structural and conformational studies regarding tryptophan in a cyclic hexapeptide somatostatin analog. In: Hruby V, Rich D, eds. Peptides: structure and function. Proceedings of the 8th American Peptide Symposium, 1983.Google Scholar
  15. 15.
    Nutt RF, Curley PE, Pitzenberger SM, Freidinger RM, Saperstein R, Veber DF. Novel conformationally constrained amino acids as lysine-9 substitutions in somatostatin analogs. Proc 9th American Pept Symp 1985; 44.Google Scholar

Copyright information

© Springer Science+Business Media New York 1987

Authors and Affiliations

  • Ruth F. Nutt
    • 1
  • C. Dylion Colton
    • 1
  • Richard Saperstein
    • 1
  • Daniel F. Veber
    • 1
  1. 1.Merck Sharp & Dohme Research LaboratoriesWest PointUSA

Personalised recommendations