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A highly sensitive fluorescent probe based on the Michael addition mechanism with a large Stokes shift for cellular thiols imaging

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Abstract

A novel fluorescent probe IPY-MAL for thiols was developed based on imidazo[1,5-α]pyridine derivative, which was decorated with a maleimide group. The probe IPY-MAL showed a rapid response (30 s), high sensitivity and selectivity for thiols with a large Stokes shift (140 nm), which was triggered by the Michael addition reaction of thiols toward the C=C double bond of the maleimide group. Moreover, this probe IPY-MAL could quantitatively detect the concentrations of thiols ranging from 0 to 50 μM, and the detection limit was found to be as low as 28 nM. Cell imaging results indicated that the probe IPY-MAL could detect and visualize thiols in the living cells.

A novel imidazo[1,5-α]pyridine-based fluorescent probe was developed for sensitively monitoring and imaging thiols in living A549 cells with a large Stokes shift.

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Acknowledgments

The research was supported by University Nursing Program for Young Scholars with Creative Talents in Heilongjiang Province (No. UNPYSCT-2017167), China.

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  1. College of Pharmacy, Qiqihar Medical University, 333 Bukui Street, Qiqihar, 161006, Heilongjiang, China

    Song Chen, Peng Hou, Jing Wang, Shuang Fu & Lei Liu

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  1. Song Chen
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Correspondence to Song Chen.

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Chen, S., Hou, P., Wang, J. et al. A highly sensitive fluorescent probe based on the Michael addition mechanism with a large Stokes shift for cellular thiols imaging. Anal Bioanal Chem 410, 4323–4330 (2018). https://doi.org/10.1007/s00216-018-1082-y

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  • DOI: https://doi.org/10.1007/s00216-018-1082-y

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