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Design and synthesis of tetrazine bioorthogonal fluorogenic probes
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Dun-yan SU1, 2, Jie LI1, Li-li PAN1, Hao-xing WU1, Wu-yu MAO1, *
Acta Pharmaceutica Sinica | 2021, 56(4) : 1086 - 1095
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Acta Pharmaceutica Sinica | 2021, 56(4): 1086-1095
Original Articles
Design and synthesis of tetrazine bioorthogonal fluorogenic probes
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Dun-yan SU1, 2, Jie LI1, Li-li PAN1, Hao-xing WU1, Wu-yu MAO1, *
Affiliations
  • 1. Department of Nuclear Medicine, West China Hospital, Sichuan University, Chengdu 610041, China
  • 2. Sichuan Polytechnic Technician College, Chengdu 611130, China
Published: 2021-04-12 doi: 10.16438/j.0513-4870.2020-1897
Outline
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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.

tetrazine  /  bioorthogonal reaction  /  pyridazine  /  turn-on fluorescent probe
Dun-yan SU, Jie LI, Li-li PAN, Hao-xing WU, Wu-yu MAO. Design and synthesis of tetrazine bioorthogonal fluorogenic probes[J]. Acta Pharmaceutica Sinica, 2021 , 56 (4) : 1086 -1095 . DOI: 10.16438/j.0513-4870.2020-1897
Year 2021 volume 56 Issue 4
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Article Info
doi: 10.16438/j.0513-4870.2020-1897
  • Receive Date:2020-12-10
  • Online Date:2025-12-18
  • Published:2021-04-12
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History
  • Received:2020-12-10
  • Revised:2021-01-11
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    1. Department of Nuclear Medicine, West China Hospital, Sichuan University, Chengdu 610041, China
    2. Sichuan Polytechnic Technician College, Chengdu 611130, China
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表12种不同金属材料的力学参数

Family
属数
Number of
genus
种数
Number of
species
占总种数比例
Percentage of
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Genus
种数
Number of
species
占总种数比例
Percentage of total
species (%)
鹅膏菌科Amanitaceae 2 11 5.26 鹅膏菌属 Amanita 10 4.78
小菇科 Mycenaceae 2 12 5.74 丝盖伞属 Inocybe 5 2.39
多孔菌科 Polyporaceae 8 14 6.70 蜡蘑属 Laccaria 5 2.39
红菇科 Russulaceae 3 23 11.00 小皮伞属 Marasmius 6 2.87
小菇属 Mycena 11 5.26
光柄菇属 Pluteus 5 2.39
红菇属 Russula 17 8.13
栓菌属 Trametes 5 2.39
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