Cyclic RGD peptide by ring-closing metathesis

被引:11
作者
Bijani, C
Varray, S
Lazaro, R
Martinez, J
Lamaty, F
Kieffer, N
机构
[1] Univ Montpellier 1, CNRS, LAPP, F-34095 Montpellier 5, France
[2] Univ Montpellier 2, CNRS, LAPP, F-34095 Montpellier, France
[3] CRP Sante, CNRS, Lab Franco Luxembourgeois Rech Biomed, Luxembourg, Luxembourg
关键词
D O I
10.1016/S0040-4039(02)00642-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A cyclic pseudopeptide containing the RGD sequence has been synthesized in high yield by ring-closing metathesis using a Grubbs' catalyst in tetrahydrofuran. Conformational analysis has been correlated to structure modeling and preliminary biological activity as an integrin binding inhibitor has been evaluated. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3765 / 3767
页数:3
相关论文
共 22 条
[1]  
ARNAOUT MA, 1990, IMMUNOL REV, P114
[2]  
BRUGGHE HF, 1994, INT J PEPT PROT RES, V43, P166
[3]   SYNTHESIS AND BINDING AFFINITIES OF CYCLIC AND RELATED LINEAR ANALOGS OF CCK8 SELECTIVE FOR CENTRAL RECEPTORS [J].
CHARPENTIER, B ;
DOR, A ;
ROY, P ;
ENGLAND, P ;
PHAM, H ;
DURIEUX, C ;
ROQUES, BP .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (06) :1184-1190
[4]   Synthesis of symmetrical dimeric N,N′-linked peptides on solid support by olefin metathesis [J].
Conde-Frieboes, K ;
Andersen, S ;
Breinholt, J .
TETRAHEDRON LETTERS, 2000, 41 (47) :9153-9156
[5]   Phenylpropionic acid-based cyclic prodrugs of opioid peptides that exhibit metabolic stability to peptidases and excellent cellular permeation [J].
Gudmundsson, OS ;
Nimkar, K ;
Gangwar, S ;
Siahaan, T ;
Borchardt, RT .
PHARMACEUTICAL RESEARCH, 1999, 16 (01) :16-23
[6]   DOUBLE-BOND ISOSTERES OF THE PEPTIDE-BOND - ENKEPHALIN ANALOG [J].
HANN, MM ;
SAMMES, PG ;
KENNEWELL, PD ;
TAYLOR, JB .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (05) :234-235
[7]   ON THE DOUBLE-BOND ISOSTERE OF THE PEPTIDE-BOND - PREPARATION OF AN ENKEPHALIN ANALOG [J].
HANN, MM ;
SAMMES, PG ;
KENNEWELL, PD ;
TAYLOR, JB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (01) :307-314
[8]  
Haubner R., 1997, ANGEW CHEM INT EDIT, V36, P1374
[9]   CONFORMATION-BASED DESIGN OF 2 CYCLIC PHYSALAEMIN ANALOGS [J].
HOLZEMANN, G ;
JONCZYK, A ;
EIERMANN, V ;
PACHLER, KGR ;
BARNICKEL, G ;
REGOLI, D .
BIOPOLYMERS, 1991, 31 (06) :691-697
[10]   INTEGRINS - VERSATILITY, MODULATION, AND SIGNALING IN CELL-ADHESION [J].
HYNES, RO .
CELL, 1992, 69 (01) :11-25