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■ Design, Synthesis and Evaluation of an L-Dopa-Derived Macrocyclic Hexaoxazole (6otd) as a G-Quadruplex-Selective Ligand

Takahiro Nakamura, Yue Ma, Keisuke Iida, Terumi Ohtake, Hiroyuki Seimiya, and Kazuo Nagasawa*

*Biotechnology and Life Science, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16, Naka-cho, Koganei, Tokyo 184-8588, Japan

Abstract

G-Quadruplex (G4) structures in guanine-rich oligonucleotides are involved in replication, transcription and translation processes in cells, and G4 dysfunction is associated with various diseases. Since G4 stabilization is believed to induce growth inhibition, senescence or apoptosis of cancer cells, various G4-stabilizing agents (G4 ligands) have been synthesized, including our recently developed series of macrocyclic polyoxazoles (OTDs). Among OTD derivatives, those bearing side-chain functional groups that interact with phosphate of the DNA backbone show potent G4-stabilizing ability. Here, we report synthesis of a new macrocyclic hexaoxazole bearing two catechol side chains, i.e., D2H4–6M(4)OTD, based upon our previously reported procedure. D2H4–6M(4)OTD showed moderate and selective stabilizing ability towards G4-forming oligonucleotides without altering their topology. It also showed moderate growth-inhibitory activity towards several cancer cell lines.