Design, synthesis and biological evaluation of carbohydrate-based mimetics of cRGDFV

被引:77
作者
Nicolaou, KC
Trujillo, JI
Chibale, K
机构
[1] Scripps Res Inst, SKAGGS INST CHEM BIOL, LA JOLLA, CA 92037 USA
[2] UNIV CALIF SAN DIEGO, DEPT CHEM & BIOCHEM, LA JOLLA, CA 92093 USA
关键词
D O I
10.1016/S0040-4020(97)00567-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The design, synthesis and preliminary biological evaluation of carbohydrate-based non-peptide mimetics of the potent peptidic antagonist of alpha(v) beta(3), and alpha(v) beta(5), pentapeptide cRGDFV (1) is presented. The design was based on the NMR-determined structure of 1. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:8751 / 8778
页数:28
相关论文
共 36 条
  • [1] ARG-GLY-ASP CONSTRAINED WITHIN CYCLIC PENTAPEPTIDES - STRONG AND SELECTIVE INHIBITORS OF CELL-ADHESION TO VITRONECTIN AND LAMININ FRAGMENT-P1
    AUMAILLEY, M
    GURRATH, M
    MULLER, G
    CALVETE, J
    TIMPL, R
    KESSLER, H
    [J]. FEBS LETTERS, 1991, 291 (01) : 50 - 54
  • [2] 1H-PYRAZOLE-1-CARBOXAMIDINE HYDROCHLORIDE - AN ATTRACTIVE REAGENT FOR GUANYLATION OF AMINES AND ITS APPLICATION TO PEPTIDE-SYNTHESIS
    BERNATOWICZ, MS
    WU, YL
    MATSUEDA, GR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) : 2497 - 2502
  • [3] Billington D C, 1991, Drug Des Discov, V8, P3
  • [4] DIRECT PREPARATION OF 2-DEOXY-D-GLUCOPYRANOSIDES FROM GLUCALS WITHOUT FERRIER REARRANGEMENT
    BOLITT, V
    MIOSKOWSKI, C
    LEE, SG
    FALCK, JR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) : 5812 - 5813
  • [5] REQUIREMENT OF VASCULAR INTEGRIN ALPHA(V)BETA(3) FOR ANGIOGENESIS
    BROOKS, PC
    CLARK, RAF
    CHERESH, DA
    [J]. SCIENCE, 1994, 264 (5158) : 569 - 571
  • [6] INTEGRIN ALPHA(V)BETA(3) ANTAGONISTS PROMOTE TUMOR-REGRESSION BY INDUCING APOPTOSIS OF ANGIOGENIC BLOOD-VESSELS
    BROOKS, PC
    MONTGOMERY, AMP
    ROSENFELD, M
    REISFELD, RA
    HU, TH
    KLIER, G
    CHERESH, DA
    [J]. CELL, 1994, 79 (07) : 1157 - 1164
  • [7] CHERESH DA, 1994, INTEGRINS MOL BIOL R
  • [8] Glycals in organic synthesis: The evolution of comprehensive strategies for the assembly of oligosaccharides and glycoconjugates of biological consequence
    Danishefsky, SJ
    Bilodeau, MT
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (13-14): : 1380 - 1419
  • [9] REGIOSELECTIVE MANIPULATION OF HYDROXYL-GROUPS VIA ORGANOTIN DERIVATIVES
    DAVID, S
    HANESSIAN, S
    [J]. TETRAHEDRON, 1985, 41 (04) : 643 - 663
  • [10] DUGGAN ME, 1996, 211 ACS NAT M NEW OR