Meiqing Zhu1, Lijun Wang1, Xiaoqin Wu2, Risong Na3, Yi Wang4, Qing X Li5, Bruce D Hammock6. 1. Collaborative Innovation Center of Henan Grain Crops, National Key Laboratory of Wheat and Maize Crop Science, College of Plant Protection, Henan Agricultural University, Wenhua Road No. 95, Zhengzhou, 450002, China; Key Laboratory of Agri-food Safety of Anhui Province, School of Resources and Environment, Anhui Agricultural University, Hefei, 230036, China. 2. Key Laboratory of Agri-food Safety of Anhui Province, School of Resources and Environment, Anhui Agricultural University, Hefei, 230036, China. 3. Collaborative Innovation Center of Henan Grain Crops, National Key Laboratory of Wheat and Maize Crop Science, College of Plant Protection, Henan Agricultural University, Wenhua Road No. 95, Zhengzhou, 450002, China. Electronic address: risongna@163.com. 4. Collaborative Innovation Center of Henan Grain Crops, National Key Laboratory of Wheat and Maize Crop Science, College of Plant Protection, Henan Agricultural University, Wenhua Road No. 95, Zhengzhou, 450002, China; Key Laboratory of Agri-food Safety of Anhui Province, School of Resources and Environment, Anhui Agricultural University, Hefei, 230036, China; Department of Entomology and UCD Comprehensive Cancer Center, School of Veterinary Medicine, University of California, Davis, CA, 95616, USA. Electronic address: wangyi1987@cau.edu.cn. 5. Department of Molecular Bioscience and Bioengineering, University of Hawaii, 1955 East-West Road, Honolulu, HI, 96822, USA. 6. Department of Entomology and UCD Comprehensive Cancer Center, School of Veterinary Medicine, University of California, Davis, CA, 95616, USA.
Abstract
Cysteine (Cys), homocysteine (Hcy) and glutathione (GSH) play many crucial physiological roles in organisms. Their abnormal levels can cause and indicate various diseases. In the present study, a small-molecule fluorescent probe 2-(imidazo[1,2-a]pyridin-2-yl)phenyl acrylate (IPPA) was designed, synthesized and characterized by NMR, FT-IR and HRMS. IPPA can selectively detect Cys over other analytes because of an approximately 76 times enhancement in fluorescence intensity. The limit of detection of IPPA for Cys was 0.33 μM. The pseudo-first-order rate constant of the reaction between IPPA and Cys was approximately 10 times that of the reaction between IPPA and Hcy (KCys 3.18 × 10-3 S-1vs KHcy 4.92 × 10-4 S-1), indicating that Cys can be distinguished from Hcy. In addition, IPPA exhibits strong anti-interference ability, small molecular weight, high efficiency, low toxicity and good cell permeability. It was successfully used in imaging HepG2 cells and zebrafish. The fluorescence response of IPPA for calf serum are powerful proofs for practical application. Therefore, IPPA has high potential for bioassay applications.
Cysteine (n class="Chemical">Cys), homocysteine (Hcy) and glutathione (GSH) play many crucial physiological roles in organisms. Their abnormal levels can cause and indicate various diseases. In the present study, a small-molecule fluorescent probe 2-(imidazo[1,2-a]pyridin-2-yl)phenyl acrylate (IPPA) was designed, synthesized and characterized by NMR, FT-IR and HRMS. IPPA can selectively detect Cys over other analytes because of an approximately 76 times enhancement in fluorescence intensity. The limit of detection of IPPA for Cys was 0.33 μM. The pseudo-first-order rate constant of the reaction between IPPA and Cys was approximately 10 times that of the reaction between IPPA and Hcy (KCys 3.18 × 10-3 S-1vs KHcy 4.92 × 10-4 S-1), indicating that Cys can be distinguished from Hcy. In addition, IPPA exhibits strong anti-interference ability, small molecular weight, high efficiency, low toxicity and good cell permeability. It was successfully used in imaging HepG2 cells and zebrafish. The fluorescence response of IPPA for calf serum are powerful proofs for practical application. Therefore, IPPA has high potential for bioassay applications.
Authors: Adam C Sedgwick; Hai-Hao Han; Jordan E Gardiner; Steven D Bull; Xiao-Peng He; Tony D James Journal: Chem Sci Date: 2018-03-16 Impact factor: 9.825
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