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.
MeSH terms
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Amines / chemical synthesis
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Amines / chemistry*
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Amines / pharmacology
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Apoptosis / drug effects
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Binding Sites / drug effects
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Cell Tracking*
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Dose-Response Relationship, Drug
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Flow Cytometry
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Fluorescent Dyes / chemical synthesis
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Fluorescent Dyes / chemistry*
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Fluorescent Dyes / pharmacology
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G-Quadruplexes*
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HeLa Cells
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Humans
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Microscopy, Fluorescence
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Molecular Structure
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Naphthalenes / chemical synthesis
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Naphthalenes / chemistry*
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Naphthalenes / pharmacology
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Proto-Oncogene Proteins c-myc / genetics*
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Structure-Activity Relationship
Substances
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Amines
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Fluorescent Dyes
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Naphthalenes
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Proto-Oncogene Proteins c-myc
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1,1'-binaphthyl