Synthesis and evaluation of potential inhibitors of eIF4E cap binding to 7-methyl GTP

被引：36
作者：
Ghosh, P
Park, C
Peterson, MS
Bitterman, PB
Polunovsky, VA
Wagner, CR [1 ]
机构：
[1] Univ Minnesota, Dept Med Chem, Minneapolis, MN 55455 USA
[2] Univ Minnesota, Dept Med, Minneapolis, MN 55455 USA
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2005年 / 15卷 / 08期
关键词：
D O I：
10.1016/j.bmcl.2005.01.080
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Cap-dependent translation is initiated by the binding of eIF4E to capped mRNA (m(7) GpppN). We have prepared a small library of 7-methyl guanosine nucleoside and nucleotide analogs and evaluated their ability to inhibit eIF4E binding to 7-methyl GTP with a competitive eIF4E binding immunoassay. 5 '-H-Phosphonate derivatives in which the 2 '- and 3 '-riboside hydroxyls were tethered together by an isopropylidene group were shown to be a new class of inhibitors of eIF4E binding to capped mRNA. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2177 / 2180
页数：4
相关论文
共 11 条
  • [1] [Anonymous], J BIOL CHEM
  • [2] Activation of translation complex eIF4F is essential for the genesis and maintenance of the malignant phenotype in human mammary epithelial cells
    Avdulov, S
    Li, S
    Michalek, V
    Burrichter, D
    Peterson, M
    Perlman, DM
    Manivel, JC
    Sonenberg, N
    Yee, D
    Bitterman, PB
    Polunovsky, VA
    [J]. CANCER CELL, 2004, 5 (06) : 553 - 563
  • [3] Quantitative assessment of mRNA cap analogues as inhibitors of in vitro translation
    Cai, A
    Jankowska-Anyszka, M
    Centers, A
    Chlebicka, L
    Stepinski, J
    Stolarski, R
    Darzynkiewicz, E
    Rhoads, RE
    [J]. BIOCHEMISTRY, 1999, 38 (26) : 8538 - 8547
  • [4] Synthesis and biological evaluation of thiazolidine-2,4-dione and 2,4-thione derivatives as inhibitors of translation initiation
    Chen, H
    Fan, YH
    Natarajan, A
    Guo, YH
    Iyasere, J
    Harbinski, F
    Luus, L
    Christ, W
    Aktas, H
    Halperin, JA
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (21) : 5401 - 5405
  • [5] INHIBITION OF EUKARYOTIC TRANSLATION BY NUCLEOSIDE 5'-MONOPHOSPHATE ANALOGS OF MESSENGER-RNA 5'-CAP - CHANGES IN N7 SUBSTITUENT AFFECT ANALOG ACTIVITY
    DARZYNKIEWICZ, E
    STEPINSKI, J
    EKIEL, I
    GOYER, C
    SONENBERG, N
    TEMERIUSZ, A
    JIN, YX
    SIJUWADE, T
    HABER, D
    TAHARA, SM
    [J]. BIOCHEMISTRY, 1989, 28 (11) : 4771 - 4778
  • [6] eIF4E - from translation to transformation
    Mamane, Y
    Petroulakis, E
    Rong, LW
    Yoshida, K
    Ler, LW
    Sonenberg, N
    [J]. ONCOGENE, 2004, 23 (18) : 3172 - 3179
  • [7] 5'-TERMINAL 7-METHYLGUANOSINE IN EUKARYOTIC MESSENGER-RNA IS REQUIRED FOR TRANSLATION
    MUTHUKRISHNAN, S
    BOTH, GW
    FURUICHI, Y
    SHATKIN, AJ
    [J]. NATURE, 1975, 255 (5503) : 33 - 37
  • [8] Biophysical studies of eIF4E cap-binding protein:: Recognition of mRNA 5′ cap structure and synthetic fragments of eIF4G and 4E-BP1 proteins
    Niedzwiecka, A
    Marcotrigiano, J
    Stepinski, J
    Jankowska-Anyszka, M
    Wyslouch-Cieszynska, A
    Dadlez, M
    Gingras, AC
    Mak, P
    Darzynkiewicz, E
    Sonenberg, N
    Burley, SK
    Stolarski, R
    [J]. JOURNAL OF MOLECULAR BIOLOGY, 2002, 319 (03) : 615 - 635
  • [9] Inhibitors of protein synthesis identified by a high throughput multiplexed translation screen
    Novac, O
    Guenier, AS
    Pelletier, J
    [J]. NUCLEIC ACIDS RESEARCH, 2004, 32 (03) : 902 - 915
  • [10] The mRNA 5′ cap-binding protein eIF4E and control of cell growth
    Sonenberg, N
    Gingras, AC
    [J]. CURRENT OPINION IN CELL BIOLOGY, 1998, 10 (02) : 268 - 275
12