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Title: Structural modification of nonspecific thiazole orange for ligand-DNA interaction study : understanding the ligand recognition selectivity towards G4-DNA over duplex-DNA
Authors: Zhu, Y
Hou, J
Huang, XH
Zhong, DX
Long, W
Liu, W
Lu, YJ
Zhang, K
Wong, WL 
Issue Date: Oct-2020
Source: Journal of luminescence, Oct. 2020, v. 226, 117488, p. 1-9
Abstract: The study of ligand interactions with nucleic acid structures such as G-quadruplexes versus double-stranded DNA is important because these interactions are fundamental for many intracellular processes. In the investigation of ligand-DNA binding process, achieving high fluorescent signal discrimination with strong binding affinity is challenging. To develop binding ligands with excellent recognition ability towards G4-DNA over duplex-DNA, the design of appropriate molecular scaffolds that are able to match with the G4-DNA binding pocket (G-quartet) is crucial. In the present study, the new fluorescent DNA binding ligands were designed and synthesized through the integration of a small and conjugated substituent group at the 2-position of the 1-methylquinolinium moiety of the nonspecific thiazole orange scaffold. The ligands were investigated in fluorescence binding assays and showed different interaction properties and significant fluorescent recognition selectivity towards G4-DNA over duplex-DNA in vitro. Molecular docking study of the ligands in complex with telo21 G4-DNA and ds26 duplex DNA also revealed different binding modes. In addition, the cytotoxicity of the fluorescent DNA binding ligands was evaluated in MTT assays against two selected cancer cell lines (human prostate cancer cell (PC3) and human hepatoma cell (hepG2)). The IC50 was found in the range of 6.3–12.5 μM, indicating a relatively high cytotoxicity of the ligands towards the cancer cells examined.
Keywords: Fluorescent binding ligand
G-quadruplex DNA recognition
Ligand-DNA interaction
Molecular docking
Publisher: Elsevier
Journal: Journal of luminescence 
EISSN: 0022-2313
DOI: 10.1016/j.jlumin.2020.117488
Rights: © 2020 Elsevier B.V. All rights reserved.
© 2020. This manuscript version is made available under the CC-BY-NC-ND 4.0 license
The following publication Zhu, Y., Hou, J., Huang, X.-H., Zhong, D.-X., Long, W., Liu, W., Lu, Y.-J., Zhang, K., & Wong, W.-L. (2020). Structural modification of nonspecific thiazole orange for ligand-DNA interaction study: Understanding the ligand recognition selectivity towards G4-DNA over duplex-DNA. Journal of Luminescence, 226, 117488 is available at
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