Citation: Yue Zhang, Wei Zhou, Ning Xu, Guangying Wang, Jin Li, Kai An, Wenchao Jiang, Xuelian Zhou, Qinglong Qiao, Xindong Jiang, Zhaochao Xu. Aniline as a TICT rotor to derive methine fluorogens for biomolecules: A curcuminoid-BF₂ compound for lighting up HSA/BSA[J]. Chinese Chemical Letters, ;2023, 34(2): 107472. doi: 10.1016/j.cclet.2022.04.070 shu

Aniline as a TICT rotor to derive methine fluorogens for biomolecules: A curcuminoid-BF₂ compound for lighting up HSA/BSA

Yue Zhang ^{a, b} ,
Wei Zhou ^b ,
Ning Xu ^b ,
Guangying Wang ^b ,
Jin Li ^b ,
Kai An ^b ,
Wenchao Jiang ^b ,
Xuelian Zhou ^b ,
Qinglong Qiao ^{b, *,} ,
Xindong Jiang ^{a, *} ,
Zhaochao Xu ^{b, *,}

a.
Liaoning & Shenyang Key Laboratory of Functional Dye and Pigment, Shenyang University of Chemical Technology, Shenyang 110142, China
b.
CAS Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China

qqlqiao@dicp.ac.cn

xdjiang@syuct.edu.cn

zcxu@dicp.ac.cn

Received Date: 18 April 2022
Revised Date: 22 April 2022
Accepted Date: 24 April 2022
Available Online: 28 April 2022

Figures(4)

The unique structure of fluorescent proteins in which the fluorophore is encapsulated by the protein shell to restrict rotation and emit light inspired the screening of chromophores that selectively bind to biomolecules to generate fluorescence. In this paper, we report a curcuminoid-BF₂-like fluorescent dye N-BF₂ containing 4-dimethylaniline as an electron-donating group. When this dye is combined with HSA or BSA, the fluorescence is enhanced 90/112-fold, and the fluorescence quantum yield increases from < 0.001 to 0.16/0.19. Such a large change in fluorescence enhancement is due to the encapsulation of N-BF₂ in the protein cavity by HSA/BSA, which inhibits the intramolecular rotation of the aniline moiety caused by charge transfer after the fluorophore is excited by light. N-BF₂ has fast and strong binding to HSA or BSA and was found to be reversible in solution and intracellularly. Since N-BF₂ also has the ability to target lipid droplets, the complex of N-BF₂/HSA realizes the regulation of reversible lipid droplet staining in cells.
- Fluorogen,
- Aniline,
- TICT,
- HSA,
- Methine dyes
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