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Molecules 2019, 24(2), 263; https://doi.org/10.3390/molecules24020263

Synthesis and Telomeric G-Quadruplex-Stabilizing Ability of Macrocyclic Hexaoxazoles Bearing Three Side Chains

1
Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan
2
Department of Chemistry, Chiba University, 1-33 Yayoi, Inage, Chiba 263-8522, Japan
3
Transborder Medical Reserch Center, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8575, Japan
4
Division of Biomedical Science, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8575, Japan
5
Molecular Profiling Research Center for Drug Discovery, National Institute of Advanced Industrial Science and Technology, 2-4-7 Aomi, Koto-ward, Tokyo 135-0064, Japan
6
Laboratoire de Biologie et Pharmacologie appliquée, CNRS UMR 8113, ENS paris-saclay 60 avenue du president Wilson, 94230 Cachan, France
7
Division of Physics and Applied Physics, Nanyang Technological University, Singapore 637371, Singapore
*
Author to whom correspondence should be addressed.
Academic Editor: Danzhou Yang
Received: 13 December 2018 / Revised: 4 January 2019 / Accepted: 10 January 2019 / Published: 11 January 2019
(This article belongs to the Special Issue G-Quadruplex Ligands and Cancer)
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Abstract

G-quadruplexes (G4s), which are structures formed in guanine-rich regions of DNA, are involved in a variety of significant biological functions, and therefore “sequence-dependent” selective G4-stabilizing agents are required as tools to investigate and modulate these functions. Here, we describe the synthesis of a new series of macrocyclic hexaoxazole-type G4 ligand (6OTD) bearing three side chains. One of these ligands, 5b, stabilizes telomeric G4 preferentially over the G4-forming DNA sequences of c-kit and K-ras, due to the interaction of its piperazinylalkyl side chain with the groove of telomeric G4. View Full-Text
Keywords: macrocyclic oxazole; G-quadruplex; telomere; telomestatin macrocyclic oxazole; G-quadruplex; telomere; telomestatin
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Ma, Y.; Iida, K.; Sasaki, S.; Hirokawa, T.; Heddi, B.; Phan, A.T.; Nagasawa, K. Synthesis and Telomeric G-Quadruplex-Stabilizing Ability of Macrocyclic Hexaoxazoles Bearing Three Side Chains. Molecules 2019, 24, 263.

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