title: Synthesis of Fluorescent Binaphthyl Amines That Bind c-MYC G-Quadruplex DNA and Repress c-MYC Expression.
abstract: Two novel binaphthyl amines have been designed and synthesized using Buchwald amination and oxidative homocoupling as key steps. The binaphthyl amine containing two triazole rings shows higher affinity for c-MYC G-quadruplex, exhibits fluorescence "turn-on" response with c-MYC, and stains the nucleus in cells. The triazolyl binaphthyl amine shows cytotoxicity for cancer cells by inducing G2/M phase cell cycle arrest and apoptosis. Moreover, both ligands can downregulate c-MYC expression at transcriptional and translational levels.
authors.affiliation: Department of Chemical Sciences, Indian Institute of Science Education and Research , Mohanpur, West Bengal 741252, India.
authors.forename: Ajay
authors.initials: A
authors.lastname: Chauhan
authors.affiliation: Department of Organic Chemistry, Indian Association for the Cultivation of Science , Jadavpur, Kolkata 700032, India.
authors.forename: Rakesh
authors.initials: R
authors.lastname: Paul
authors.affiliation: Department of Organic Chemistry, Indian Association for the Cultivation of Science , Jadavpur, Kolkata 700032, India.
authors.forename: Manish
authors.initials: M
authors.lastname: Debnath
authors.affiliation: Institute of Organic Chemistry and Chemical Biology, Center for Biomolecular Magnetic Resonance (BMRZ), Goethe University Frankfurt , Max-von-Laue Strasse 7, 60438 Frankfurt am Main, Germany.
authors.forename: Irene
authors.initials: I
authors.lastname: Bessi
authors.affiliation: Department of Organic Chemistry, Indian Association for the Cultivation of Science , Jadavpur, Kolkata 700032, India.
authors.forename: Samir
authors.initials: S
authors.lastname: Mandal
authors.affiliation: Institute of Organic Chemistry and Chemical Biology, Center for Biomolecular Magnetic Resonance (BMRZ), Goethe University Frankfurt , Max-von-Laue Strasse 7, 60438 Frankfurt am Main, Germany.
authors.forename: Harald
authors.initials: H
authors.lastname: Schwalbe
authors.affiliation: Department of Chemical Sciences, Indian Institute of Science Education and Research , Mohanpur, West Bengal 741252, India.|Department of Organic Chemistry, Indian Association for the Cultivation of Science , Jadavpur, Kolkata 700032, India.
authors.forename: Jyotirmayee
authors.initials: J
authors.lastname: Dash
mesh_terms: D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects; D001665:Binding Sites / Q000187:drug effects; D058948:Cell Tracking; D004305:Dose-Response Relationship, Drug; D005434:Flow Cytometry; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D054856:G-Quadruplexes; D006367:HeLa Cells; D006801:Humans; D008856:Microscopy, Fluorescence; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D016271:Proto-Oncogene Proteins c-myc / Q000235:genetics*; D013329:Structure-Activity Relationship
chemical_list: D000588:Amines; D005456:Fluorescent Dyes; D009281:Naphthalenes; D016271:Proto-Oncogene Proteins c-myc; C412330:1,1'-binaphthyl