Issue 29, 2017

Near-infrared BODIPY-based two-photon ClO probe based on thiosemicarbazide desulfurization reaction: naked-eye detection and mitochondrial imaging

Abstract

Hypochlorite serves as a significant antimicrobial agent in the human immune system, and its detection is of great importance. Herein, a novel near-infrared BODIPY-based ClO fluorescent probe (NCS-BOD-OCH3) was designed and synthesized. The emission bands of NCS-BOD-OCH3 concentrated at 595 nm and 665 nm. Since the electron withdrawing group 1,3,4-oxadiazole was formed after the desulfurization reaction, the fluorescence intensity of NCS-BOD-OCH3 decreased significantly in THF/H2O (v/v, 1 : 1, buffered with 10 mM PBS pH = 7.4), which is visible to the naked eye with an obvious color change. NCS-BOD-OCH3 can realize the two-photon up-converted fluorescence emission. The low detection limit was calculated from the titration results, with the figure for NCS-BOD-OCH3/ClO being 1.15 × 10−6 M. The result of living cell imaging experiment demonstrated that NCS-BOD-OCH3 can successfully detect ClO in living cells and can serve as a NIR mitochondrial imaging agent. It is an excellent platform for developing NIR ClO fluorescent probes.

Graphical abstract: Near-infrared BODIPY-based two-photon ClO− probe based on thiosemicarbazide desulfurization reaction: naked-eye detection and mitochondrial imaging

Supplementary files

Article information

Article type
Paper
Submitted
16 May 2017
Accepted
26 Jun 2017
First published
26 Jun 2017

J. Mater. Chem. B, 2017,5, 5854-5861

Near-infrared BODIPY-based two-photon ClO probe based on thiosemicarbazide desulfurization reaction: naked-eye detection and mitochondrial imaging

B. Shen, Y. Qian, Z. Qi, C. Lu, Q. Sun, X. Xia and Y. Cui, J. Mater. Chem. B, 2017, 5, 5854 DOI: 10.1039/C7TB01344B

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