Synthesis,G-Quadruplex DNA binding and cytotoxic properties of naphthalimide substituted styryl dyes |
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| Affiliation: | 1. School of Pharmacy, Guilin Medical University, Guilin 541004, China;2. Department of Chemistry & Pharmaceutical Science, Guilin Normal College, Guangxi 541001, China;1. Institute of Inorganic Chemistry, Academy of Sciences of the Czech Republic, v.v.i., Hlavní 1001, CZ-250 68 Řež, Czech Republic;2. Department of Organic Chemistry, Faculty of Sciences, Charles University, Hlavova 2030, 128 42 Prague 2, Czech Republic;3. Institute of Medical Biology, Polish Academy of Sciences, 106 Lodowa St., Lodz 93-232, Poland;4. Institute of Bioorganic Chemistry, Polish Academy of Sciences, 12/14 Z. Noskowskiego St., 61–704 Poznan, Poland;5. Department of Pharmacodynamics, Medical University of Lodz, 1 Muszynskiego St., 90-151 Lodz, Poland;1. Department of Chemistry, Biology and Biotechnology and “Centro di Eccellenza Materiali Innovativi Nonostrutturati” (CEMIN), Via Elce di Sotto 8, 06123, Perugia, Italy;2. Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, 10000, Zagreb, Croatia;1. Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev str., bl. 9, 1113 Sofia, Bulgaria;2. Department of Pharmaceutical and Applied Organic Chemistry, Faculty of Chemistry, University of Sofia, 1164 Sofia, Bulgaria;3. Laboratory for Biomolecular Interactions and Spectroscopy, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička c. 54, 10000 Zagreb, Croatia;4. Laboratory for Molecular Plant Biology and Biotechnology, Division of Molecular Biology, Ruđer Bošković Institute, Bijenička c. 54, 10000 Zagreb, Croatia;1. Biophysics Department, Research and Clinical Center for Physical Chemical Medicine, Malaya Pirogovskaya Str. 1a, Moscow, 119435, Russia;2. Moscow Institute of Physics and Technology, Institutsky Lane 9, Dolgoprudny, 141700, Russia;3. Department of Molecular Virology, FSBI Research Institute of Influenza, Ministry of Health of Russian Federation, Prof. Popov Str. 15/17, Saint-Petersburg, 197376, Russia;4. Computational Oncology Group, I.M. Sechenov First Moscow State Medical University, Bolshaya Pirogovskaya Str. 19/1, Moscow, 119146, Russia;5. Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya Str. 16/10, Moscow, 117997, Russia;6. Institute of Bioengineering, Research Center of Biotechnology of the Russian Academy of Sciences, Leninsky Prospect, 33, Build. 2, Moscow, 119071, Russia;7. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov Str. 32, Moscow, 119991, Russia;1. The State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, China;2. School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR China;3. International Healthcare Innovation Institute (Jiangmen), Jiangmen 529040, PR China;4. Department of Chemistry, Lakehead University and Thunder Bay Regional Health Research Institute, 980 Oliver Road, Thunder Bay, ON P7B 6V4, Canada;5. Institute of Natural Medicine and Green Chemistry, School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, PR China |
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| Abstract: | G-Quadruplex DNAs, formed by G-rich DNA sequences in human genes, are promising targets for design of cancer drugs. In this study, two naphthalimide substituted styryl dyes with different sizes of aromatic groups were synthesized. The spectral analysis showed that the dye X-2 with a large aromatic group formed aggregates in buffer solution displaying very weak fluorescence intensity, and disaggregated in the presence of G-Quadruplex DNAs with large intensity enhancements (up to ~1800 fold). Moreover, X-2 displayed good selectivity to G-Quadruplex DNAs. In contrast, dye X-3 with the smaller aromatic group had much lower fluorescence enhancements and poor selectivity to G-Quadruplex DNAs, suggesting that the suitably sized aromatic ring was essential for the interaction with G-Quadruplex. Further binding studies suggested that X-2 mainly bound on G-quartet surface through end-stacking mode. Cytotoxicity assay showed that both of the two dyes showed good anti-proliferative activities against the cancer cell lines and less cytotoxicity in non-malignant cell lines, which were better than a standard drug 5-fluorouracil. In addition, living cell imaging was also studied and demonstrated the potential applications of the new dye X-2 in bioassays and cell imaging. |
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| Keywords: | G-Quadruplex DNA Naphthalimide Styryl dyes Aggregation Anticancer |
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