Citation: Shi-Jie LI, Xiao-Ting QIAN, Yuan-Lei HUANG, Xu-Ling XUE, Yong QIAN, Zhi SU, Hong-Ke LIU. Click-chemistry synthesis and antitumor properties of cyclometalated iridium(Ⅲ) complex based on oleanolic acid[J]. Chinese Journal of Inorganic Chemistry, ;2023, 39(2): 317-326. doi: 10.11862/CJIC.2022.289 shu

Click-chemistry synthesis and antitumor properties of cyclometalated iridium(Ⅲ) complex based on oleanolic acid

School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210023, China

Corresponding author: Xu-Ling XUE, xuexuling87@163.com Hong-Ke LIU, liuhongke@njnu.edu.cn
Received Date: 20 August 2022
Revised Date: 9 November 2022

Figures(6)

Herein, we modified the natural product oleanolic acid with alkyne to synthesize the ligand OA-alkyne, and tethered it with cyclic metal iridium precursor CycloIr-N₃ to obtain the final complex CycloIr-OA via copper(Ⅰ)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. The ligand and the complex were characterized by ¹H NMR and ESI-MS. The results show that the complex had good lipophilicity, which was helpful to enter the cells quickly. The antitumor activity of CycloIr-OA and the mechanism of inducing tumor cell death were further studied by MTT, confocal imaging, and flow cytometry. After oleanolic acid was linked, the anti - cancer activity of complex CycloIr-OA was greatly improved. CycloIr-OA is enriched in the mitochondria of tumor cells, leading to the production of reactive oxygen species, and at the same time, it blocks the cell cycle in the S phase, ultimately inducing tumor cell necrosis.
- cyclometalated iridium complex,
- oleanolic acid,
- antitumor,
- necrosis
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