PMID: 6172157Dec 18, 1981Paper

Interaction of tryptophan-modified analogues of cholecystokinin-octapeptide with cholecystokinin receptors on pancreatic acini

Biochimica Et Biophysica Acta
H AdachiJ D Gardner

Abstract

None of six different tryptophan-modified analogues of the C-terminal octapeptide of cholecystokinin differed from the unaltered peptide in terms of their efficacies for stimulating amylase secretion from dispersed acini prepared from guinea-pig pancreas. Replacement of hydrogen with fluorine in position 5 or 6 on the indole ring of the tryptophan residue did not alter the potency with which the peptide stimulated amylase secretion; however, replacement of hydrogen by fluorine in positions 4, 5, 6 and 7 of the indole ring, or modifying or replacing the indole nitrogen caused a 30- to 300-fold decrease in potency. Changes in the ability of the peptide to inhibit binding of 125I-labeled cholecystokinin. Our findings indicate that reducing the ability of the tryptophan residue to donate electrons produced a greater decrease in the affinity of the peptide for cholecystokinin receptors than did abolishing the ability of tryptophan to form hydrogen bonds, and modification that altered both abilities caused a greater decrease in affinity than did modification of only one ability. Finally, in the tryptophan residues of cholecystokinin octapeptide, tetrafluorination of the indole ring or replacing the indole nitrogen by oxygen reduced t...Continue Reading

References

Mar 1, 1977·Acta Endocrinologica·J W van NispenL Schenkel-Hulliger
Jan 1, 1975·International Journal of Peptide and Protein Research·J W Van Nispen, G I Tesser
Jul 1, 1979·International Journal of Peptide and Protein Research·H M RajhG I Tesser
Dec 1, 1976·Chemical & Pharmaceutical Bulletin·Y YabeY Baba
May 14, 1968·Proceedings of the Royal Society of London. Series B, Containing Papers of a Biological Character·J S Morley
May 1, 1970·Journal of Medicinal Chemistry·K HofmannL Moroder
Oct 15, 1980·Biochimica Et Biophysica Acta·H M RajhR J Nivard
Apr 1, 1980·Proceedings of the National Academy of Sciences of the United States of America·R T JensenJ D Gardner
Mar 1, 1980·International Journal of Peptide and Protein Research·H M RajhR J Nivard

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