Synthesis, singlet oxygen generation, photocytotoxicity and subcellular localization of azobisporphyrins as potentially photodynamic therapeutic agents in vitro cell study

Yunman Zheng, Sizhe Zhu, Lijun Jiang, Fengshou Wu, Chi Huang, Zaoying Li, Ka-Leung WONG, Zebin Xu, Kai Wang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

Three azobisporphyrins (Por1, Por2 and Por3) were synthesized by coupling two molecules of (4-nitrophenyl/pyridyl) porphyrins in the presence of KOH/butanol. The structures of porphyrins were confirmed by UV, IR, NMR and mass spectra and elemental analysis. With tetraphenylporphyrin (H2TPP) as a control, the singlet oxygen (1O2) generation of porphyrins was evaluated through 1,3-diphenylisobenzofuran (DPBF) method. The order of ability to generate 1O2 for three azobisporphyrins was Por 1 ≈Por 2 > Por 3 ≈H2TPP. The photocytotoxicity and sub-cellular localization of azobisporphyrins over Hela cells were studied through MTT analysis and confocal laser scanning microscope, respectively. The results indicated Por 1 and Por 2 displayed the low dark-cytotoxicity, while Por 3 induced a concentration-dependent cytotoxicity to Hela cells with the concentration of porphyrins ranging from 1 to 100 μM. With the light dose at 4 J/cm2, Por 3 killed more than 60% Hela cells at 2 μM, indicating a high photocytoxicity. As seen from the laser scanning confocal microscopy images, Por 3 was mainly localized in cell membrane, while Por 1 and Por 2 do not displayed significant fluorescent emission in Hela cells. These results suggest the synthesized cationic azobisporphyrin could be used as a potential therapeutic agent for photodynamic therapy of cancers.

Original languageEnglish
Pages (from-to)122-127
Number of pages6
JournalJournal of Porphyrins and Phthalocyanines
Volume21
Issue number2
DOIs
Publication statusPublished - 1 Feb 2017

Scopus Subject Areas

  • Chemistry(all)

User-Defined Keywords

  • Azobisporphyrin
  • Cell localization
  • Pdt
  • Photocytotoxicity
  • Singlet oxygen

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