“AIE+ESIPT” based naphthothiazole fluorescent probes for live cell imaging

•Naphthothiazole fluorescent probes, HNBT-H and HNBT-G, based on the "AIE+ESIPT" effect, were prepared.•The photophysical properties of HNBT, HNBT-H and HNBT-G were thoroughly studied.•The capability of HNBT-H and HNBT-G for fluorescence visualization in response to β-gal and H2O2 in RAW26...

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Veröffentlicht in:Journal of molecular structure 2025-01, Vol.1319, p.139542, Article 139542
Hauptverfasser: Fu, Chunmei, Li, Junhong, Wang, Yihan, Feng, Shiting, Wang, Sha, Chen, Hongyu, Wu, Peng, Zhang, Haitao, Yan, Xinhao
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Sprache:eng
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Zusammenfassung:•Naphthothiazole fluorescent probes, HNBT-H and HNBT-G, based on the "AIE+ESIPT" effect, were prepared.•The photophysical properties of HNBT, HNBT-H and HNBT-G were thoroughly studied.•The capability of HNBT-H and HNBT-G for fluorescence visualization in response to β-gal and H2O2 in RAW264.7 cells and PC12 cells have been successfully demonstrated. Dual-functional organic fluorophores with aggregation induced emission (AIE) behavior and excited-state intramolecular proton transfer (ESIPT) behavior are of great significance to the design of imaging probes to bioimage systems. However, the pursuit of probes exhibiting dual AIE+ESIPT effects for live cell imaging remains an ongoing research challeng. Herein, we have successfully developed naphthothiazole fluorescent probes, HNBT-H and HNBT-G, based on the "AIE+ESIPT" effect. These probes were designed by incorporating responsive units for β-galactosidase (β-gal) and H2O2 into the pre-existing "AIE+ESIPT" HNBT fluorophore framework. The HNBT-H probe demonstrated the capability to distinguish various levels of H2O2. Furthermore, the applicability of HNBT-H and HNBT-G have been examined in living systems. These probes exhibit a good biocompatibility and low toxicity, the cell imaging experiments demonstrate the capability of HNBT-H and HNBT-G for fluorescence visualization in response to β-gal and H2O2 in RAW264.7 cells and PC12 cells. [Display omitted]
ISSN:0022-2860
DOI:10.1016/j.molstruc.2024.139542