Chinese Journal of Organic Chemistry >
Synthesis of Nopinone-Based Quinazolin-2-amine Fluorescent Probe for Detection of Cu2+ and Its Application Research
Received date: 2020-08-26
Revised date: 2020-10-22
Online published: 2020-11-04
Supported by
National Natural Science Foundation of China(32071707); Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, and the Priority Academic Program Development of Jiangsu Higher Education Institutions
In this study, a novel nopinone-based quinazolin-2-amine fluorescent probe N-benzyl-4-(4-(diethylamino)phenyl)- 7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinazolin-2-amine (BNQ) was synthesized from renewable β-pinene derivative nopinone. The probe BNQ exhibited a high selective fluorescence quenching response toward Cu2+in PBS/THF (V/V=8/2, 10 mmol?L–1, pH=7.4) solution, and could effectively recognize Cu2+ within a wide pH range (4~10). Meanwhile, the fluorescent titration experiment showed that the probe BNQ was high sensitive for detecting Cu2+, and its detection limit was found to be 0.09 μmol?L –1, which was much lower than that of stated by World Health Organization (WHO) in drinking water (<30 μmol?L–1). Furthermore, the coordination mechanism of probe BNQ with Cu2+ was confirmed by high resolution mass spectrum (HRMS) and density functional theory (DFT) calculations. The probe BNQ could detect micromolar Cu2+ in different environmental water samples. The results of bio-imaging experiment demonstrated that the probe BNQwas also successfully used for monitoring Cu2+ in living zebrafish, and showed an excellent fluorescence imaging performance.
Key words： nopinone; quinazolin-2-amine; fluorescent probe; Cu2+ ion; bioimaging
Mingguang Zhang , Mingxin Li , Yiqin Yang , Xu Xu , Jie Song , Zhonglong Wang , Shifa Wang . Synthesis of Nopinone-Based Quinazolin-2-amine Fluorescent Probe for Detection of Cu2+ and Its Application Research[J]. Chinese Journal of Organic Chemistry, 2021 , 41(3) : 1168 -1176 . DOI: 10.6023/cjoc202008049
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