Synthesis of asymmetric cationic zinc porphyrin photosensitizer containing thiophene group for photodynamic therapy in vitro and theoretical calculation of DFT

被引：5

作者：

Zhang, Wen-Yuan ^{[1
]}

Li, Gui-Chen ^{[2
]}

Wang, Bo ^{[1
]}

Fan, Yan ^{[1
]}

Sun, Xue-Qin ^{[1
]}

Yang, Yi-Xin ^{[1
]}

Zhang, Chun-Yan ^{[1
]}

Feng, Xiao-Xia ^{[1
]}

Xu, Wei-Bing ^{[2
]}

Liu, Jia-Cheng ^{[1
]}

机构：

[1] Northwest Normal Univ, Coll Chem Chem Engn, Key Lab Bioelectrochemistry & Environm Anal Gansu, Key Lab Ecoenvironm Related Polymer Mat,Minist Edu, Lanzhou 730070, Peoples R China

[2] Gansu Agr Univ, State Key Lab Aridland Crop Sciencee, Lanzhou 730000, Peoples R China

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2024年 / 1302卷

关键词：

Porphyrin; ROS; Photosensitizer; Photodynamic therapy; PSEUDOPOTENTIALS; SUBSTITUENTS; DERIVATIVES; DELIVERY;

D O I：

10.1016/j.molstruc.2024.137497

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Porphyrins, as photosensitizers for photodynamic therapy, is used to treat various cancers. In this study, three different side-chain variants of thiophene-zinc porphyrins were synthesized (Zn-P1, Zn-P2, and Zn-P3). Among the synthesized compounds, Zn-P1 exhibited the highest activity and demonstrated superior singlet oxygen generation capability according to both density functional theory calculations and singlet oxygen generation experiments. Our cytotoxicity assays revealed that Zn-P1 exhibited remarkable phototoxicity along with a pronounced selectivity for HepG2 cells. This selectivity was confirmed by cell staining experiments, which showed obvious apoptotic processes. Further insight into this anticancer mechanism was provided by cell reactive oxygen species experiments, which explained the induction of cancer cell apoptosis. Light-activated production of reactive oxygen species by photosensitizers initiates the apoptotic cascade in cancer cells. This study highlights the utility of cationic porphyrin photosensitizer complexes in photodynamic therapy and provides new insights for the development of innovative photosensitizers in cancer treatment.

引用

页数：9

共 69 条

[1] Toward reliable density functional methods without adjustable parameters: The PBE0 model [J].