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A model for a biologically active conformation of somatostatin is proposed. This model is based primarily on the biological results obtained with novel bicyclic somatostatin analogs having a covalent bridge replacing the side chains of residues 5 and 10, 6 and 11, and 5 and 12, respectively, rather than on physical measurements on the hormone in solution. The high activity of an analog in which Phe6 and Phe11 are replaced by cystine provides evidence that these phenylalanines stabilize the biologically active conformer through "hydrophobic bonding" but do not directly interact with the receptor. The synthesis of the novel bicyclic analogs of somatostatin and the effects of these on the inhibition of secretion of insulin, glucagon, growth hormone, and gastric acid are described.
D F Veber, and
F W Holly, and
W J Paleveda, and
R F Nutt, and
S J Bergstrand, and
M Torchiana, and
M S Glitzer, and
R Saperstein, and
R Hirschmann
September 2011,
Chemical reviews,
D F Veber, and
F W Holly, and
W J Paleveda, and
R F Nutt, and
S J Bergstrand, and
M Torchiana, and
M S Glitzer, and
R Saperstein, and
R Hirschmann
April 2009,
Organic & biomolecular chemistry,
D F Veber, and
F W Holly, and
W J Paleveda, and
R F Nutt, and
S J Bergstrand, and
M Torchiana, and
M S Glitzer, and
R Saperstein, and
R Hirschmann
January 1985,
Proceedings of the National Academy of Sciences of the United States of America,
D F Veber, and
F W Holly, and
W J Paleveda, and
R F Nutt, and
S J Bergstrand, and
M Torchiana, and
M S Glitzer, and
R Saperstein, and
R Hirschmann
June 2004,
Bioorganic & medicinal chemistry letters,
D F Veber, and
F W Holly, and
W J Paleveda, and
R F Nutt, and
S J Bergstrand, and
M Torchiana, and
M S Glitzer, and
R Saperstein, and
R Hirschmann
January 1993,
Advances in experimental medicine and biology,
D F Veber, and
F W Holly, and
W J Paleveda, and
R F Nutt, and
S J Bergstrand, and
M Torchiana, and
M S Glitzer, and
R Saperstein, and
R Hirschmann
August 1999,
Bioorganic & medicinal chemistry letters,
D F Veber, and
F W Holly, and
W J Paleveda, and
R F Nutt, and
S J Bergstrand, and
M Torchiana, and
M S Glitzer, and
R Saperstein, and
R Hirschmann
October 1990,
International journal of peptide and protein research,
D F Veber, and
F W Holly, and
W J Paleveda, and
R F Nutt, and
S J Bergstrand, and
M Torchiana, and
M S Glitzer, and
R Saperstein, and
R Hirschmann
June 1987,
Die Pharmazie,
D F Veber, and
F W Holly, and
W J Paleveda, and
R F Nutt, and
S J Bergstrand, and
M Torchiana, and
M S Glitzer, and
R Saperstein, and
R Hirschmann
December 2005,
Bioorganic & medicinal chemistry letters,
D F Veber, and
F W Holly, and
W J Paleveda, and
R F Nutt, and
S J Bergstrand, and
M Torchiana, and
M S Glitzer, and
R Saperstein, and
R Hirschmann
March 1991,
International journal of peptide and protein research,
