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Target identification of a macrocyclic hexaoxazole G-quadruplex ligand using post-target-binding visualization
- Source :
- Chemical communications (Cambridge, England). 56(85)
- Publication Year :
- 2020
-
Abstract
- Macrocyclic hexaoxazoles (6OTDs) are G-quadruplex (G4) ligands, and some derivatives, such as L2H2-6OTD (1a) bearing two aminobutyl side chains, show cytotoxicity towards cancer cells. To identify the cellular target of 1a, we employed a post-target-binding strategy utilizing click reaction (Huisgen cyclization) between the azide-conjugated ligand L2H2-6OTD-Az (1b) and the cell-permeable dye CO-1 bearing a strained alkyne moiety and the BODIPY fluorophore under Cu-free conditions. We confirmed that introduction of the small azide group did not alter the physical or biological properties, including anti-cancer activity, of 1a, and we also demonstrated bias-free localization of CO-1. The post-binding visualization strategy suggested that L2H2-6OTD (1a) colocalized with RNA G4 in living cells.
- Subjects :
- Fluorophore
Macrocyclic Compounds
Stereochemistry
Alkyne
010402 general chemistry
G-quadruplex
Ligands
01 natural sciences
Catalysis
03 medical and health sciences
chemistry.chemical_compound
Cell Line, Tumor
Materials Chemistry
Moiety
Humans
Oxazoles
030304 developmental biology
chemistry.chemical_classification
0303 health sciences
Binding Sites
Molecular Structure
Chemistry
Ligand
Metals and Alloys
General Chemistry
0104 chemical sciences
Surfaces, Coatings and Films
Electronic, Optical and Magnetic Materials
G-Quadruplexes
Ceramics and Composites
Click chemistry
Azide
BODIPY
Subjects
Details
- ISSN :
- 1364548X
- Volume :
- 56
- Issue :
- 85
- Database :
- OpenAIRE
- Journal :
- Chemical communications (Cambridge, England)
- Accession number :
- edsair.doi.dedup.....35ea5868f23d6702801bb86c3af295ed