Synthesis, optical properties, and cellular imaging of novel quinazolin-2-amine nopinone derivatives. (May 2016)

• Record Type: Journal Article
• Authors: Yang, Jinlai; Xu, Haijun; Xu, Xu; Rui, Jian; Fang, Xianying; Cao, Xiaoqin; Wang, Shifa
• Is Part Of: Dyes and pigments. Volume 128(2016)
• Page Start: 75
• Page End: 83
• Publication Date: 2016-05
• Subjects: Nopinone -- Quinazolin-2-amine derivatives -- Synthesis -- Fluorescence enhancement -- Fluorescence quenching -- Fluorescence bio-imaging; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2016.01.016
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: Quinazolin-2-amine derivatives (4 –6 ) were successfully synthesized from β-pinene derivative nopinone and characterized by Fourier transform infrared spectroscope (FT-IR), nuclear magnetic resonance (NMR), mass spectrometry, and X-ray single crystal diffraction. Then, their optical and thermal properties were characterized with ultraviolet–visible spectroscopy, photoluminescence (PL) spectroscopy, thermogravimetric analysis, and confocal fluorescent microscopic imaging. Three target compounds had enhanced fluorescence in solid and solution states and fluorescent quenching occurred when acid or base was added to the solution. Thermal decomposition temperatures of compounds4 –6 were 138, 290, and 291 °C, respectively and no compound was cytotoxic to normal L02 hepatocyte cells, and confocal fluorescent microscopic imaging in human lung A549 adenocarcinoma cells was realized using these compounds. These new fluorescent compounds may be candidates for future fluorescent bio-imaging agents. Graphical abstract: Highlights: Novel quinazolin-2-amine derivatives were designed and synthesized from nopinone. Quinazolin-2-amine derivatives had fluorescent properties in the solid and solution states. Quinazolin-2-amine derivatives had little cytotoxicity to L02 cells. Quinazolin-2-amine derivatives can be used for cellular imaging.