Citation: Zhang Peng, Guo Zhi-Qian, Yan Chen-Xu, Zhu Wei-Hong. Near-Infrared mitochondria-targeted fluorescent probe for cysteine based on difluoroboron curcuminoid derivatives[J]. Chinese Chemical Letters, ;2017, 28(10): 1952-1956. doi: 10.1016/j.cclet.2017.08.038 shu

Near-Infrared mitochondria-targeted fluorescent probe for cysteine based on difluoroboron curcuminoid derivatives

a.
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Shanghai Key Laboratory of Functional Materials Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China
b.
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China

Corresponding author: Guo Zhi-Qian, guozq@ecust.edu.cn
Received Date: 1 June 2017
Revised Date: 4 August 2017
Accepted Date: 21 August 2017
Available Online: 25 October 2017

Figures(7)

Curcuminoid difluoroboron has attractive performance as a promising near-infrared (NIR) fluorescent dye. In this contribution, we designed and synthesized a mitochondria-targeted NIR fluorescent probe DFB1 based on difluoroboron curcuminoid scaffold for the detection of Cys (cysteine). DFB1 employs a curcumin analog as the NIR fluorophore, an acrylate group containing α, β-unsaturated ketone as a functional trigger moiety for Cys, and a triphenylphosphonium (TPP) cation moiety for specifically targeting mitochondria. The remarkable shift of DFB1 with Cys was observed from 470 nm to 590 nm in absorption spectra and from 560 nm to 680 nm in emission spectra. Notably, DFB1 manifests significantly dual-channel and turn-on NIR fluorescent signals simultaneously in response to Cys concentration, which make it favorable for monitoring endogenous Cys activity in vivo. This probe has high sensitivity and selectivity for the detection of Cys over homocysteine (Hcy) and glutathione (GSH). This specific response for Cys was based on differences kinetics of intramolecular adduct/cyclizations. More importantly, biological experiments indicated that this probe could be utilized for the detection of endogenous mitochondrial Cys in living cells.
- Near-infrared,
- Fluorescent probe,
- Dual-channel,
- Cysteine,
- Curcuminoid
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1.
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