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CCK8 peptide derivatized with diphenylphosphine for rhenium labelling: synthesis and molecular mechanics calculations
Author(s) -
Morelli Giancarlo,
De Luca Stefania,
Tesauro Diego,
Saviano Michele,
Pedone Carlo,
Dolmella Alessandro,
Visentin Roberta,
Mazzi Ulderico
Publication year - 2002
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.400
Subject(s) - chemistry , rhenium , chelation , peptide , moiety , cysteine , phosphine , ligand (biochemistry) , stereochemistry , combinatorial chemistry , receptor , organic chemistry , biochemistry , enzyme , catalysis
A novel CCK8 derivative bearing a chelating agent at its N ‐ end and its oxo‐rhenium(V) complex have been synthesized and characterized. The chelating agent N ‐{ N ‐[3‐(diphenylphosphino)propionyl]glycyl} cysteine (PN 2 S) ligand, the coordination set of which is made by the phosphorus atom of phosphine, the nitrogen atoms of the two amido groups and the sulphur atom of cysteine, has been used due to its high affinity towards the oxo‐rhenium(V) moiety. Molecular modelling studies indicate that the CCK8 peptide adopts the right conformation for cholecystokinin receptor binding, and that modifications on the N ‐terminal side of CCK8 obtained by introducing chelating agents and its metal complexes should not affect the interaction with CCK A receptor. Copyright © 2002 European Peptide Society and John Wiley & Sons, Ltd.