Citation: Xu Qu, Baohua Ji, Haocheng Gong, Guangwei Wang, Liang-Liang Gao, Jing Zhang, Jianjian Zhang, Yuan Guo. Dual-emissive near-infrared fluorogenic probe with enhanced cellular uptake capability for sensitive tracking of cellular polarity[J]. Chinese Chemical Letters, ;2025, 36(10): 110766. doi: 10.1016/j.cclet.2024.110766 shu

Dual-emissive near-infrared fluorogenic probe with enhanced cellular uptake capability for sensitive tracking of cellular polarity

Xu Qu ^{a, b, 1} ,
Baohua Ji ^{b, 1} ,
Haocheng Gong ^{b, 1} ,
Guangwei Wang ^b ,
Liang-Liang Gao ^b ,
Jing Zhang ^{a, c, *,} ,
Jianjian Zhang ^{b, *,} ,
Yuan Guo ^{a, b, *,}

a.
School of Chemical Engineering, Engineering Research Center of Western Resource Innovation Medicine Green Manufacturing of the Ministry of Education, Northwest University, Xi'an 710127, China
b.
College of Chemistry and Materials Science, Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, Northwest University, Xi'an 710127, China
c.
Shaanxi Chinese Medicine Institute Shaanxi Pharmaceutical Information Centre, Xi'an 712000, China

1016686871@qq.com

zhangjj@nwu.edu.cn

guoyuan@nwu.edu.cn

Received Date: 22 October 2024
Revised Date: 11 December 2024
Accepted Date: 13 December 2024
Available Online: 16 December 2024

Figures(4)

Polarity, as a crucial environmental characteristic, plays a significant role in numerous cellular physiological processes. Abnormal changes in polarity are closely associated with various diseases. However, existing tools still have certain limitations that hinder accurate detection of polarity. Therefore, there is a pressing need to develop powerful tools for precisely monitoring changes in polarity. In this study, we developed two dual-emissive fluorogenic dyes by innovatively introducing 1,3-dithio-2-heteroarsenic cyclopentane and 1,2-diselenocyclopentane respectively into the near-infrared (NIR) coumarin-benzopyranium skeleton to enhance their cellular uptake capability. Additionally, we synthesized the polarity-sensitive dual-emissive fluorogenic probe CSFNS, which exhibits high cellular uptake rate, by modifying the spironolactone (Aldactone) structure of CBA into spirolactam. CSFNS not only demonstrates excellent polarity sensitivity in vitro but is also successfully applied to visually monitor the polarity changes in various types of living cells, including healthy cells, cancer cells and drug-induced senescent cells.
- Cellular polarity,
- Near-infrared,
- Fluorogenic probe,
- High cellular uptake,
- 1,3-Dithio-2-heteroarsenic
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