Improved Synthesis of Guanine Quadruplex Ligand Phen-DC3

An Improved Route for the Synthesis of Guanine Quadruplex Ligand Phen-DC3: C. E. Miron, A. Petitjean
Synlett 2018, DOI: 10.1055/s-0036-1591994

The guanine quadruplex (G4) is an oligonucleotide structure that has been observed to form in certain guanine-rich DNA or RNA sequences through cation-stabilized π-π stacking of guanine tetrads, each composed of four guanines interacting through hydrogen bonding. Targeting G4 is coming of age as an attractive strategy for anticancer and antiviral applications. Phen-D3 is a bisquinolinium compound exhibiting both high affinity binding to G4 and excellent selectivity for G4 over other architectures, whose improved synthesis has recently been reported by the group of Professor Anne Petitjean from Queen’s University (Kingston, Canada).

Professor Petitjean said: “Phen-DC3, developed by the Teulade-Fichou group, is a selective and robust guanine quadruplex binder, very useful as a benchmark for analysis of new DNA ligands, albeit expensive; this improved synthetic sequence facilitates access to significant quantities with limited cost and environmental impact.”
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