Near-infrared BODIPY-based two-photon ClO− probe based on thiosemicarbazide desulfurization reaction: naked-eye detection and mitochondrial imaging. Issue 29 (12th July 2017)

• Record Type: Journal Article
• Authors: Shen, Bao-xing; Qian, Ying; Qi, Zheng-qing; Lu, Chang-gui; Sun, Qi; Xia, Xiang; Cui, Yi-ping
• Is Part Of: Journal of materials chemistry. Volume 5:Issue 29(2017)
• Page Start: 5854
• Page End: 5861
• Publication Date: 2017-07-12
• Subjects: Materials -- Periodicals; Chemistry, Analytic -- Periodicals; Biomedical materials -- Research -- Periodicals; 543.0284
• DOI: 10.1039/c7tb01344b
• Languages: English
• ISSNs: 2050-750X

Abstract

Abstract : Near-infrared two-photon ClO − fluorescent probe based on the desulfurization reaction of the thiosemicarbazide group. 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 ofNCS-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 ofNCS-BOD-OCH3 decreased significantly in THF/H2 O (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 forNCS-BOD-OCH3 /ClO − being 1.15 × 10 −6 M. The result of living cell imaging experiment demonstrated thatNCS-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.