Total synthesis of a biotinylated rocaglate: Selective targeting of the translation factors eIF4AI/II

Bioorganic & Medicinal Chemistry Letters
2016.0

Abstract

The total synthesis of a biotinylated derivative of methyl rocaglate is described. This compound was accessed from synthetic methyl rocaglate (2) via formation of the propargyl amide and subsequent click reaction with a biotin azide. Affinity purification revealed that biotinylated rocaglate (8) and methyl rocaglate (2) bind with high specificity to translation factors eIF4AI/II. This remarkable selectivity is in line with that found for the more complex rocaglate silvestrol (3).

Knowledge Graph

Similar Paper

Total synthesis of a biotinylated rocaglate: Selective targeting of the translation factors eIF4AI/II
Bioorganic & Medicinal Chemistry Letters 2016.0
Design, synthesis, and biological evaluation of biotin-labeled (−)-ternatin, a potent fat-accumulation inhibitor against 3T3-L1 adipocytes
Bioorganic & Medicinal Chemistry Letters 2009.0
Synthesis and antitumor activity of biotinylated camptothecin derivatives as potent cytotoxic agents
Bioorganic & Medicinal Chemistry Letters 2019.0
Design and Synthesis of Biotinylated Bivalent Carboline Derivatives as Potent Antitumor Agents
The Journal of Organic Chemistry 2020.0
Synthesis and Biological Evaluation of a Biotinylated Paclitaxel with an Extra-Long Chain Spacer Arm
ACS Medicinal Chemistry Letters 2012.0
Design of Development Candidate eFT226, a First in Class Inhibitor of Eukaryotic Initiation Factor 4A RNA Helicase
Journal of Medicinal Chemistry 2020.0
Biotin Derivatives Carrying Two Chelating DOTA Units. Synthesis, in Vitro Evaluation of Biotinidases Resistance, Avidin Binding, and Radiolabeling Tests
Journal of Medicinal Chemistry 2010.0
‘Click’ glycosylation of peptides through cysteine propargylation and CuAAC
Bioorganic & Medicinal Chemistry 2014.0
Synthetic Analogue of Rocaglaol Displays a Potent and Selective Cytotoxicity in Cancer Cells: Involvement of Apoptosis Inducing Factor and Caspase-12
Journal of Medicinal Chemistry 2009.0
Diastereoselective synthesis of (2S,4R)-4-Methylglutamic acid (sym 2081): A high affinity and selective ligand at the kainate subtype of glutamate receptors
Bioorganic & Medicinal Chemistry Letters 1995.0