title: Molecular Engineering of Thiazole Orange Dye: Change of Fluorescent Signaling from Universal to Specific upon Binding with Nucleic Acids in Bioassay.
abstract: The universal fluorescent staining property of thiazole orange (TO) dye was adapted in order to be specific for G-quadruplex DNA structures, through the introduction of a styrene-like substituent at the ortho-position of the TO scaffold. This extraordinary outcome was determined from experimental studies and further explored through molecular docking studies. The molecular docking studies help understand how such a small substituent leads to remarkable fluorescent signal discrimination between G-quadruplex DNA and other types of nucleic acids. The results reveal that the modified dyes bind to the G-quadruplex or duplex DNA in a similar fashion as TO, but exhibit either enhanced or quenched fluorescent signal, which is determined by the spatial length and orientation of the substituent and has never been known. The new fluorescent dye modified with a p-(dimethylamino)styryl substituent offers 10-fold more selectivity toward telomeric G-quadruplexes than double-stranded DNA substrates. In addition, native PAGE experiments, FRET, CD analysis, and live cell imaging were also studied and demonstrated the potential applications of this class of thiazole-orange-based fluorescent probes in bioassays and cell imaging.
authors.affiliation: Institute of Natural Medicine and Green Chemistry, School of Chemical Engineering and Light Industry, Guangdong University of Technology , Guangzhou 510006, Peoples' Republic of China.
authors.forename: Yu-Jing
authors.initials: YJ
authors.lastname: Lu
authors.affiliation: Institute of Natural Medicine and Green Chemistry, School of Chemical Engineering and Light Industry, Guangdong University of Technology , Guangzhou 510006, Peoples' Republic of China.
authors.forename: Qiang
authors.initials: Q
authors.lastname: Deng
authors.affiliation: London Regional Cancer Program , 790 Commissioners Road East, London, Ontario N6A 4L6, Canada.
authors.forename: Jin-Qiang
authors.initials: JQ
authors.lastname: Hou
authors.affiliation: Institute of Natural Medicine and Green Chemistry, School of Chemical Engineering and Light Industry, Guangdong University of Technology , Guangzhou 510006, Peoples' Republic of China.
authors.forename: Dong-Ping
authors.initials: DP
authors.lastname: Hu
authors.affiliation: Institute of Natural Medicine and Green Chemistry, School of Chemical Engineering and Light Industry, Guangdong University of Technology , Guangzhou 510006, Peoples' Republic of China.
authors.forename: Zheng-Ya
authors.initials: ZY
authors.lastname: Wang
authors.affiliation: Institute of Natural Medicine and Green Chemistry, School of Chemical Engineering and Light Industry, Guangdong University of Technology , Guangzhou 510006, Peoples' Republic of China.
authors.forename: Kun
authors.initials: K
authors.lastname: Zhang
authors.affiliation: London Regional Cancer Program , 790 Commissioners Road East, London, Ontario N6A 4L6, Canada.|Departments of Oncology, Chemistry, Medical Imaging, The University of Western Ontario , London, Ontario N6A 3K7, Canada.
authors.forename: Leonard G
authors.initials: LG
authors.lastname: Luyt
authors.affiliation: Department of Science and Environmental Studies, Centre for Education in Environmental Sustainability, The Hong Kong Institute of Education , 10 Lo Ping Road, Tai Po, Hong Kong SAR, Peoples' Republic of China.
authors.forename: Wing-Leung
authors.initials: WL
authors.lastname: Wong
authors.affiliation: Department of Science and Environmental Studies, Centre for Education in Environmental Sustainability, The Hong Kong Institute of Education , 10 Lo Ping Road, Tai Po, Hong Kong SAR, Peoples' Republic of China.
authors.forename: Cheuk-Fai
authors.initials: CF
authors.lastname: Chow
mesh_terms: D052160:Benzothiazoles / Q000737:chemistry*; D001681:Biological Assay; D004591:Electrophoresis, Polyacrylamide Gel; D009690:Nucleic Acid Conformation; D009696:Nucleic Acids / Q000378:metabolism*; D011804:Quinolines / Q000737:chemistry*; D015398:Signal Transduction
chemical_list: D052160:Benzothiazoles; D009696:Nucleic Acids; D011804:Quinolines; C051000:thiazole orange