Carbazole-based fluorescent probes for G-quadruplex DNA targeting with superior selectivity and low cytotoxicity |
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| Affiliation: | 1. Department of Chemistry, College of Science, Huazhong Agricultural University, Wuhan, 430070, PR China;2. College of Veterinary Medicine, Huazhong Agricultural University, Wuhan, 430070, PR China;3. State Key Laboratory of Agricultural Microbiology, Huazhong Agricultural University, Wuhan, 430070, PR China;1. Drug Design and Synthesis Lab, Department of Chemistry, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, India;2. Laboratory of Functional Genomics and Molecular Toxicology, CSIR-Central Drug Research Institute, (CSIR-CDRI), Jankipuram Extension, Sitapur Road, Lucknow 226031, India;1. School of Chemistry and Chemical Engineering & Center for Atomic Engineering of Advanced Materials, Anhui University, Hefei 230039, PR China;2. Department of Materials and Chemical Engineering, Chizhou University, Chizhou 247000, PR China;1. School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen, 518060, China;2. Zhuhai Institute for Food and Drug Control, Zhuhai, 519000, China;3. School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, China |
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| Abstract: | G-quadruplex DNA plays a very important role in clinical diagnosis and fluorescence analysis has attracted extensive attention. A class of carbazole-based fluorescent probes for the detection of G-quadruplex DNA was established in this work. In this system, the installation of an oligo(ethylene glycol) chain on the scaffold will improve the water-solubility and biocompatibility. The presence of styrene-like different side groups could tune the selectivity toward G-quadruplex DNA binding. Results revealed that the substitution pattern and position gave a great influence on the ability for the discrimination of the G-quadruplex from other DNA structures. Especially, probe E1 bound to G-quadruplex DNA with superior selectivity, which exhibiting almost no fluorescence response in the presence of non-G-quadruplex DNA structures. Comprehensive analyses revealed that E1 could bind both ends of the G-quadruplex, resulting in a significant increase of fluorescence emission intensity. Cellular uptake assay suggested that E1 could pass through membrane and enter living cells with low cytotoxicity. |
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| Keywords: | G-quadruplex DNA Fluorescent probe Carbazole Cell imaging Cytotoxicity |
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