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 [J].

Avdulov, S ;

Li, S ;

Michalek, V ;

Burrichter, D ;

Peterson, M ;

Perlman, DM ;

Manivel, JC ;

Sonenberg, N ;

Yee, D ;

Bitterman, PB ;

Polunovsky, VA .

CANCER CELL, 2004, 5 (06) :553-563

[3] Quantitative assessment of mRNA cap analogues as inhibitors of in vitro translation [J].

Cai, A ;

Jankowska-Anyszka, M ;

Centers, A ;

Chlebicka, L ;

Stepinski, J ;

Stolarski, R ;

Darzynkiewicz, E ;

Rhoads, RE .

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 [J].

Chen, H ;

Fan, YH ;

Natarajan, A ;

Guo, YH ;

Iyasere, J ;

Harbinski, F ;

Luus, L ;

Christ, W ;

Aktas, H ;

Halperin, JA .

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 [J].

DARZYNKIEWICZ, E ;

STEPINSKI, J ;

EKIEL, I ;

GOYER, C ;

SONENBERG, N ;

TEMERIUSZ, A ;

JIN, YX ;

SIJUWADE, T ;

HABER, D ;

TAHARA, SM .

BIOCHEMISTRY, 1989, 28 (11) :4771-4778

[6] eIF4E - from translation to transformation [J].

Mamane, Y ;

Petroulakis, E ;

Rong, LW ;

Yoshida, K ;

Ler, LW ;

Sonenberg, N .

ONCOGENE, 2004, 23 (18) :3172-3179

[7] 5'-TERMINAL 7-METHYLGUANOSINE IN EUKARYOTIC MESSENGER-RNA IS REQUIRED FOR TRANSLATION [J].

MUTHUKRISHNAN, S ;

BOTH, GW ;

FURUICHI, Y ;

SHATKIN, AJ .

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 [J].

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 .

JOURNAL OF MOLECULAR BIOLOGY, 2002, 319 (03) :615-635

[9] Inhibitors of protein synthesis identified by a high throughput multiplexed translation screen [J].

Novac, O ;

Guenier, AS ;

Pelletier, J .

NUCLEIC ACIDS RESEARCH, 2004, 32 (03) :902-915

[10] The mRNA 5′ cap-binding protein eIF4E and control of cell growth [J].

Sonenberg, N ;

Gingras, AC .

CURRENT OPINION IN CELL BIOLOGY, 1998, 10 (02) :268-275