Environmental mimic of receptor interaction: conformational analysis of CCK-15 in solution

J Med Chem. 2002 Feb 14;45(4):762-9. doi: 10.1021/jm0109457.

Abstract

CCK-15, a peptide derived from the 115-membered CCK preprohormone, was the object of a comparative conformational analysis by NMR spectroscopy and molecular modeling methods. NMR data in several solvents demonstrate that the propensity of the peptide to fold into a helical conformation is intrinsic, not merely a consequence of the interaction with phosphatidylcholine micelles or with a putative receptor, as suggested by a previous study on CCK-8 (Pellegrini, M.; Mierke, D. Biochemistry 1999, 38, 14775-14783.). The prevailing CCK-15 conformer in a mixture 1,1,1,3,3,3-hexafluoroacetone/water reveals that the residues common to CCK-15 and CCK-8 assume very similar conformations. Our CCK-15 structure is consistent with the model of receptor interaction proposed by Pellegrini and Mierke and discloses possible novel interactions that involve a larger area of the putative receptor. The consensus structure between CCK-15 and CCK-8 shows a good superposition of the side chains of residues 12-14 with crucial moieties of two non-peptidic CCK-A antagonists.

MeSH terms

  • Acetone / analogs & derivatives*
  • Cholecystokinin / chemistry*
  • Circular Dichroism
  • Dimethyl Sulfoxide
  • Fluorocarbons
  • Magnetic Resonance Spectroscopy
  • Micelles
  • Models, Molecular
  • Peptide Fragments / chemistry*
  • Protein Structure, Secondary
  • Receptor, Cholecystokinin A
  • Receptors, Cholecystokinin / chemistry*
  • Solutions
  • Solvents
  • Water

Substances

  • CCK 15
  • Fluorocarbons
  • Micelles
  • Peptide Fragments
  • Receptor, Cholecystokinin A
  • Receptors, Cholecystokinin
  • Solutions
  • Solvents
  • cholecystokinin 8
  • Water
  • Acetone
  • Cholecystokinin
  • hexafluoroacetone
  • Dimethyl Sulfoxide