Syntheses of BODIPY photosensitizers and their photodynamic effect on tumor cells
10.3785/j.issn.1008-9292.2017.04.04
- VernacularTitle:氟硼二吡咯类光敏剂的制备及对肿瘤细胞的光动力学影响
- Author:
Xingang LIU
1
;
Min WU
;
Suying LI
;
Zhongbao LI
;
Qinglian HU
;
Jun ZHOU
;
Guping TANG
Author Information
1. 浙江大学化学系
- Keywords:
Photochemotherapy;
Photosensitizing agents/pharmacokinetics;
Photosensitizing agents/therapeutic use;
Neoplasms/therapy;
Tumor cells,cultured/ drug effects;
Spectrometry,fluorescence;
Spectrum analysis;
Pyrroles/pharmacology
- From:
Journal of Zhejiang University. Medical sciences
2017;46(2):135-143
- CountryChina
- Language:Chinese
-
Abstract:
Objective:To design and synthesize photosensitizers with different substituents and to identify its physicochemical characteritics and photodynamic effect on tumor cells.Methods:Two kinds of BODIPY photosensitizers BPOI and BPCI were synthesized through condensation reaction between aldehyde and reactive hydrogen of pyrrole,followed with electrophilic substitution reaction.Physicochemical properties were characterized by 1H NMR,FT-IR and UV-visible absorption spectra and fluorescence emission spectra.The ability to produce reactive oxygen species was detected by BPDF and DCFH-DA.Photodynamic therapy effect on rat glioma C6 cells in vitro was determined by MTT method.Results:Two kinds of BODIPY photosensitizers BPOI and BPCI were successfully synthesized with different substituents,which were confirmed by 1H NMR,FT-IR.Both materials had low toxicity and could be readily taken up by tumor cells.The ability of synthesized photosensitizers to produce reactive oxygen species was strongly influenced by solvent polarity when the substituent belongs to electron-donating group,while no effect was found when the substituent belongs to electron-withdrawing group.Conclusion:Photosensitizer BPOI with electron-donating substituent produces reactive oxygen species with a slow rate in a highly polar environment,while the ability to produce reactive oxgen is greatly improved in a low polarity environment,which is expected to be used for environmental-selective photodynamic therapy in tumor cells.
