Novel unsymmetrical silicon(IV) phthalocyanines as highly potent anticancer photosensitizers. Synthesis, characterization, and in vitro photodynamic activities. (June 2020)

• Record Type: Journal Article
• Authors: Zheng, Bi-Yuan; Wang, Lei; Hu, Qing-Yan; Shi, Jie; Ke, Mei-Rong; Huang, Jian-Dong
• Is Part Of: Dyes and pigments. Volume 177(2020)
• Publication Date: 2020-06
• Subjects: Silicon(IV) phthalocyanine -- Unsymmetrical -- Tyramine -- Oligomeric ethylene glycol -- Photodynamic therapy; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2020.108286
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: A series of novel unsymmetrical silicon (IV) phthalocyanines (SiPcs) di-substituted axially with tyramine and different oligomeric ethylene glycol moieties have been synthesized by alkoxy exchange reactions, and their singlet oxygen quantum yields ( Φ Δ ) and in vitro photodynamic activities have also been evaluated. The unsymmetrical SiPcs 2 –5 show slightly higher photosensitizing efficiency ( Φ Δ = 0.08–0.12) than the corresponding symmetrical SiPc 1 ( Φ Δ = 0.05), but are less efficient compared to the symmetrical SiPc 6 ( Φ Δ = 0.33). All the compounds exhibit high photocytotoxicities against BGC-823 cancer cells with IC50 values ranging from 3 nM to 20 nM. Particularly for the unsymmetrical SiPc 5, the IC50 value toward BGC-823 cells is significantly lower than its corresponding symmetrical SiPcs 1 and 6, which could be attributed to its higher cellular uptake. In addition, SiPc 5 can essentially bind to mitochondria and induces cell death of BGC-823 cells mainly through apoptosis. So SiPc 5 is a highly promising photosensitizer for photodynamic therapy. Graphical abstract: Image 1 Highlights: Four novel unsymmetrical SiPcs substituted with tyramine and different oligomeric ethylene glycol moieties are synthesized. The structure-activity relationship of these silicon (IV) phthalocyanines was discussed. The unsymmetrical SiPc 5 showed the highest photodynamic activity against BGC-832 cells as a result of high cellular uptake.