Design and synthesis of tetrazine bioorthogonal fluorogenic probes
10.16438/j.0513-4870.2020-1897
- VernacularTitle:荧光增强型四嗪生物正交荧光探针的设计与合成
- Author:
Dun-yan SU
1
,
2
;
Jie LI
1
;
Li-li PAN
1
;
Hao-xing WU
1
;
Wu-yu MAO
1
Author Information
1. Department of Nuclear Medicine, West China Hospital, Sichuan University, Chengdu 610041, China
2. Sichuan Polytechnic Technician College, Chengdu 611130, China
- Publication Type:Research Article
- Keywords:
tetrazine;
bioorthogonal reaction;
pyridazine;
turn-on fluorescent probe
- From:
Acta Pharmaceutica Sinica
2021;56(4):1086-1095
- CountryChina
- Language:Chinese
-
Abstract:
Bioorthogonal fluorogenic probes are becoming an ideal tool for live-cell fluorescence imaging. With the tetrazine bioorthogonal fluorogenic probe that displays fluorescence enhancement, the tetrazine plays the dual-role of a bioorthogonal reaction unit and the fluorescence quenching unit. The "off" and "on" states of the fluorescence probe are mainly controlled through inverse electron demand Diels-Alder (IEDDA) bioorthogonal reaction. We designed a series of turn-on tetrazine fluorescent probes with Donor-π-Acceptor (D-π-A) structure to achieve a high signal-to-noise ratio and specificity of fluorescence imaging. This series of probes reacted with the dienophile bicyclononyne, and then generated pyridazine structure in-situ that acted as an electron acceptor, resulting in a new D-π-A effect of fluorescent dyes, turning on the intramolecular charge transfer (ICT) effect. By adjusting the electron-donating groups and the degree of conjugation, tunable fluorescence spectra between 400-647 nm with fluorescence turn-on enhanced up to 500-fold have been achieved. This research lays the foundation for the further optimization of tetrazine bioorthogonal fluorescent probes and their applications in molecular imaging and biomedical fields.
