Tetrazine bioorthogonal click-to-release reaction for releasing peptides
10.16438/j.0513-4870.2020-0139
- VernacularTitle:四嗪生物正交点击-释放反应释放多肽研究与应用
- Author:
Xiao-meng WANG
1
;
Jie LI
2
;
Guo-hua SHEN
1
;
Li-li PAN
1
;
Rong TIAN
1
;
Hong-bao SUN
2
;
Hao-xing WU
2
Author Information
1. Department of Nuclear Medicine, West China Hospital, Sichuan University, Chengdu 610041, China
2. Huaxi MR Research Center, West China Hospital, Sichuan University, Chengdu 610041, China
- Publication Type:Research Article
- Keywords:
tetrazine;
italic>trans-cyclooctene;
bioorthogonal reaction;
solid-phase peptidesynthesis;
click-to-release reaction
- From:
Acta Pharmaceutica Sinica
2020;55(7):1634-1646
- CountryChina
- Language:Chinese
-
Abstract:
This paper aimed to investigate the release efficiency of peptide at carbon terminal triggered by tetrazine bioorthogonal click-to-release reaction, and further explored the potential application of this reaction in functional modification and mild cleavage in solid-phase peptide synthesis. Thirteen peptide derivatives modified by trans-cyclooctene (TCO) were designed and synthesized, which were reacted with tetrazine to release the peptides. The results showed that the release rates of peptide were 90.0% to 97.7% in one hour. The strategy has good compatibility with the functional side-groups and the length of peptides, which expands the applications scope of tetrazine bioorthogonal click-to-release reaction. At the same time, a novel bifunctional trans-cyclooctene molecule was designed and synthesized. The active peptide GIRLRG was modified by fluorophore on the solid-phase resin, and released through tetrazine click-to-release reaction under mild condition, providing a new strategy for the solid-phase modification and release strategy of the peptide.
