Issue 28, 2023

A facile ratiometric near-infrared fluorescent probe using conjugated 1,8-naphthalimide and dicyanoisophorone with a vinylene linker for detection and bioimaging of hypochlorite

Abstract

A new ratiometric near-infrared fluorescent probe 3 for detecting ClO using conjugated 1,8-naphthalimide and dicyanoisophorone with a vinylene linker was reported. Probe 3 exhibited a ratiometric signal (I705/I535), large Stokes shift (205 nm), high selectivity and sensitivity, low detection limit (0.738 μM), rapid response (within 3 s) and good biocompatibility. The sensing mechanism involved the oxidation of the olefin double bond by ClO to release the initial N-butyl-4-hydroxyl-3-formyl-1,8-naphthalimide 1, followed by inhibition of an ICT process from the electron-donor 4-hydroxyl-1,8-naphthalimide to dicyanoisophorone. At the same time, the probe 3-loaded test strips were applied in sensing of ClO with moderate “naked-eye” color changes. Additionally, probe 3 has been successfully used for ratiometric bioimaging of ClO in HeLa cells with low cytotoxicity.

Graphical abstract: A facile ratiometric near-infrared fluorescent probe using conjugated 1,8-naphthalimide and dicyanoisophorone with a vinylene linker for detection and bioimaging of hypochlorite

Supplementary files

Article information

Article type
Paper
Submitted
22 May 2023
Accepted
27 Jun 2023
First published
27 Jun 2023

Anal. Methods, 2023,15, 3420-3425

A facile ratiometric near-infrared fluorescent probe using conjugated 1,8-naphthalimide and dicyanoisophorone with a vinylene linker for detection and bioimaging of hypochlorite

Z. Zhang, L. Ma, Y. Huang, Y. Zhou, H. Zhang, J. Yan and C. Liu, Anal. Methods, 2023, 15, 3420 DOI: 10.1039/D3AY00820G

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