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Molecules 2013, 18(4), 4328-4341; doi:10.3390/molecules18044328

Evaluation of the Interaction between Long Telomeric DNA and Macrocyclic Hexaoxazole (6OTD) Dimer of a G-quadruplex Ligand

1
Faculty of Technology, Tokyo University of Agriculture and Technology (TUAT), 2-24-16 Naka-cho, Koganei-shi, Tokyo 185-0031, Japan
2
Cancer Chemotherapy Center, Japanese Foundation for Cancer Research (JFCR), 3-8-31 Ariake, Koto-ku, Tokyo 135-8550, Japan
*
Author to whom correspondence should be addressed.
Received: 12 March 2013 / Revised: 2 April 2013 / Accepted: 9 April 2013 / Published: 12 April 2013
(This article belongs to the Special Issue Macrocyclic Chemistry)
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Abstract

Macrocyclic hexaoxazole dimer of L2H2-6OTD-dimer (3) was newly synthesized as a telomeric G-quadruplex (G4) ligand, and interaction with long telomeric DNAs telo48, 72, and 96 was evaluated by means of electrophoresis mobility shift assay, CD spectra analysis, and CD melting experiments. The L2H2-6OTD-dimer (3) interacted with the long telomeric DNAs by inducing anti-parallel type G4 structure of each unit of 24 bases, i.e., (TTAGGG)4 sequences. Dimer 3 stabilizes long telomeric DNAs more efficiently than the corresponding monomer of L2H2-6OTD (2). It showed potent inhibitory activity against telomerase, with an IC50 value of 7.5 nm.
Keywords: macrocycles; G-quadruplex; telomestatin; telomere; oxazole macrocycles; G-quadruplex; telomestatin; telomere; oxazole
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Iida, K.; Majima, S.; Nakamura, T.; Seimiya, H.; Nagasawa, K. Evaluation of the Interaction between Long Telomeric DNA and Macrocyclic Hexaoxazole (6OTD) Dimer of a G-quadruplex Ligand. Molecules 2013, 18, 4328-4341.

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