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Novel Flavonoid Photoswitchable “Turn-On” Fluorescent Chemosensors: Synthesis of Bromo Flavonols for Nanomolar Aluminum Ion Detection and Cellular Imaging, among Other Applications

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Abstract

Aluminum (Al), a non-essential element in living systems, can potentially cause chronic toxicity. Therefore, it is crucial to have a specific and sensitive method for detecting Al3+ in order to assess its risk to life. In this study, we designed and synthesized a novel fluorescent probe (IV) based on bromoflavonol. Upon binding to Al3+, probe IV exhibits a blue shift in emission and enhanced fluorescence, making it suitable for Al3+ detection. Our UV-Vis absorption and fluorescence emission spectra demonstrate that probe IV has high selectivity and sensitivity towards Al3+ while being immune to interference from other metal ions. Through fluorescence titration, we determined that the detection limit (LOD) of probe IV for Al3+ is 1.8 × 10−8 mol/L. Job’s curve and 1 H NMR titration further confirmed a 1:1 binding stoichiometry between probe IV and Al3+. Additionally, using DFT (Density Functional Theory), we calculated the energy gap difference between IV and IV + Al3+ and found that the complex formed by probe IV and Al3+ is more stable than IV alone. We successfully detected Al3+ in tap water and river water from the middle regions of the Han River, achieving recoveries of over 96% using this probe. This demonstrates its potential for quantitative detection of Al3+ in environmental water samples. Moreover, we successfully used the probe for imaging Al3+ in MG63 cells, suggesting its potential application in biological imaging.

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Funding

This work was supported by The Brainstorm Project on Social Development by the Department of Science and Technology of Shaanxi Province (2022SF-356), National Natural Science Youth Fund (22101165). Work in Bailin Zhao’s lab was funded by the National Natural Science Foundation of China (22104120).

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Authors and Affiliations

  1. Shaanxi Key Laboratory of Catalysis, School of Chemistry and Environment Science, Shaanxi University of Technology, 723000, Hanzhong, Shaanxi, China

    Chaona An, Cunfang liu, Bo Liu & Guanghui Tian

  2. Key Laboratory of Environment and Disease Genetics, Ministry of Education, Xi’an Jiaotong University, Xi’an, Shaanxi, 710061, China

    Hengyi Li

  3. Institute of Molecular and Translational Medicine (IMTM), Department of Biochemistry and Molecular Biology, Xi’an Jiaotong University Health Science Center, Xi’an, 710061, Shaanxi, China

    Di Liu, Wenlong Wang, Chenyang Zhang & Bailin Zhao

Authors
  1. Chaona An
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  2. Hengyi Li
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  3. Cunfang liu
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  4. Di Liu
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  5. Wenlong Wang
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  6. Chenyang Zhang
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  7. Bailin Zhao
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  8. Bo Liu
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  9. Guanghui Tian
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Contributions

Chaona An contributed to the methodology, investigations, probe preparation, data collection and curation, and writing-original draft preparation. Hengyi Li, Cunfang liu, Di Liu, Wenlong Wang, Chenyang Zhang, Bo Liu contributed to methodology development, data collection, and sample pretreatment. Guanghui Tian and Bailin Zhao performed conceptualization, supervision, writing-review.

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Correspondence to Chaona An.

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An, C., Li, H., liu, C. et al. Novel Flavonoid Photoswitchable “Turn-On” Fluorescent Chemosensors: Synthesis of Bromo Flavonols for Nanomolar Aluminum Ion Detection and Cellular Imaging, among Other Applications. J Fluoresc (2023). https://doi.org/10.1007/s10895-023-03469-9

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