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- Title
Cationic Pentaheteroaryls as Selective G-Quadruplex Ligands by Solvent-Free Microwave-Assisted Synthesis.
- Authors
Petenzi, Michele; Verga, Daniela; Largy, Eric; Hamon, Florian; Doria, Filippo; Teulade-Fichou, Marie-Paule; Guédin, Aurore; Mergny, Jean-Louis; Mella, Mariella; Freccero, Mauro
- Abstract
We report herein a solvent-free and microwaved-assisted synthesis of several water soluble acyclic pentaheteroaryls containing 1,2,4-oxadiazole moieties ( 1- 7). Their binding interactions with DNA quadruplex structures were thoroughly investigated by FRET melting, fluorescent intercalator displacement assay (G4-FID) and CD spectroscopy. Among the G-quadruplexes considered, attention was focused on telomeric repeats together with the proto-oncogenic c-kit sequences and the c-myc oncogene promoter. Compound 1, and to a lesser extent 2 and 5, preferentially stabilise an antiparallel structure of the telomeric DNA motif, and exhibit an opposite binding behaviour to structurally related polyoxazole ( TOxaPy), and do not bind duplex DNA. The efficiency and selectivity of the binding process was remarkably controlled by the structure of the solubilising moieties.
- Publication
Chemistry - A European Journal, 2012, Vol 18, Issue 45, p14487
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201202097