Synthesis and biological evaluation of cyclic and branched peptide analogues as ligands for cholecystokinin type I receptor

被引：4
作者：
De Luca, Stefania
De Capua, Antonia
Saviano, Michele
Della Moglie, Raffaella
Aloj, Luigi
Tarallo, Laura
Pedone, Carlo
Morelli, Giancarlo
机构：
[1] CNR, Inst Biostrutture & Bioimmagini, I-80134 Naples, Italy
[2] CIRPeB, I-80134 Naples, Italy
[3] Fdn G Pascale, Ist Nazl Studio & Cura Tumori, Dept Nucl Med, I-80131 Naples, Italy
[4] Fdn G Pascale, Ist Nazl Studio & Cura Tumori, Unit Anim Experimentat, I-80131 Naples, Italy
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2007年 / 15卷 / 17期
关键词：
cholecystokinin; cyclic constraints; cyclic peptides; receptor binding affinity;
D O I：
10.1016/j.bmc.2007.05.067
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A library of cyclic CCK8 analogues, containing unnatural amino acids in the peptide sequence, is prepared using solid-phase synthesis. The structure of these cyclic peptides is based oil a previously synthesised compound, cyclo-CCK8, selective for CCK1 receptor. Structure-activity investigations are performed by evaluating the binding properties of the new analogues. In particular, the binding ability of the cyclic CCK8 analogues is tested by nuclear medicine studies on cell line transfected with CCK1 receptor. Compounds named cyclo-A4-cyclo-A7 show binding constant in the range 6.0-8.0 mu M, with an improved affinity over the previous described cyclo-CCK8, but almost comparable IC50 values among new analogues towards CCK1 were obtained. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5845 / 5853
页数：9
相关论文
共 24 条
[1]   Modeled structure of a G-protein-coupled receptor: The Cholecystokinin-1 receptor [J].
Archer-Lahlou, E ;
Tikhonova, I ;
Escrieut, C ;
Dufresne, M ;
Seva, C ;
Pradayrol, L ;
Moroder, L ;
Maigret, B ;
Fourmy, D .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (01) :180-191
[2]   COHERENCE TRANSFER BY ISOTROPIC MIXING - APPLICATION TO PROTON CORRELATION SPECTROSCOPY [J].
BRAUNSCHWEILER, L ;
ERNST, RR .
JOURNAL OF MAGNETIC RESONANCE, 1983, 53 (03) :521-528
[3]  
*COMP AID RES ASS, 2004, ROCH KELL
[4]   BIOLOGICAL ACTIONS OF CHOLECYSTOKININ [J].
CRAWLEY, JN ;
CORWIN, RL .
PEPTIDES, 1994, 15 (04) :731-755
[5]   New synthetic strategy for o-NBS protected amino acids and their use in synthesis of mono-benzylated peptides [J].
De Luca, S ;
Della Moglie, R ;
De Capua, A ;
Morelli, G .
TETRAHEDRON LETTERS, 2005, 46 (39) :6637-6640
[6]   A cyclic CCK8 analogue selective for the cholecystokinin type A receptor: Design, synthesis, NMR structure and binding measurements [J].
De Luca, S ;
Ragone, R ;
Bracco, C ;
Digilio, G ;
Aloj, L ;
Tesauro, D ;
Saviano, M ;
Pedone, C ;
Morelli, G .
CHEMBIOCHEM, 2003, 4 (11) :1176-1187
[7]  
de Tullio P, 1999, CURR MED CHEM, V6, P433
[8]   CLASSIFICATION AND FUNCTION OF CCK RECEPTORS [J].
DOURISH, CT ;
HILL, DR .
TRENDS IN PHARMACOLOGICAL SCIENCES, 1987, 8 (06) :207-208
[9]   Cholecystokinin and gastrin receptors [J].
Dufresne, Marlene ;
Seva, Catherine ;
Fourmy, Daniel .
PHYSIOLOGICAL REVIEWS, 2006, 86 (03) :805-847
[10]   Structure of cholecystokinin receptor binding sites and mechanism of activation/inactivation by agonists/antagonists [J].
Fourmy, D ;
Escrieut, C ;
Archer, E ;
Galès, C ;
Gigoux, V ;
Maigret, B ;
Moroder, L ;
Silvente-Poirot, S ;
Martinez, J ;
Fehrentz, JA ;
Pradayrol, L .
PHARMACOLOGY & TOXICOLOGY, 2002, 91 (06) :313-320
123