Fluorinated dendritic silicon (IV) phthalocyanines nanoparticles: Synthesis, photoinduced intramolecular energy transfer and DNA interaction. (February 2021)

• Record Type: Journal Article
• Authors: Xiao, Wenling; Guan, Xinqiao; Huang, Bingcheng; Ye, Qiuhao; Zhang, Tiantian; Chen, Kuizhi; Peng, Yiru; Fu, Fangmeng
• Is Part Of: Dyes and pigments. Volume 186(2021)
• Publication Date: 2021-02
• Subjects: Fluorinated dendrimer -- Phthalocyanine -- Photophysical properties -- Polymeric nanoparticles -- DNA photocleavage -- Photodynamic therapy; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2020.109013
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: Two series of fluorinated and non-fluorinated dendritic silicon (IV) phthalocyanines with cyano/nitro/ester terminal functionalities have been synthesized. Their structures were characterized by elemental analysis, FT-IR, 1 H NMR and ESI-MS. The effects of fluorinated groups and terminal functionalities properties on the photophysical properties, photoinduced intermolecular electron transfer and intramolecular energy transfer of silicon phthalocyanines were compared. In order to endow water soluble and biocompatibility to these silicon phthalocyanines, an amphiphilic diblock copolymer polyethylene glycol monomethyl ether–polycaprolactone was used to encapsulate these silicon phthalocyanines to form fluorinated and non-fluorinated dendritic silicon phthalocyanines nanoparticles. The binding model between the fluorinated dendritic silicon phthalocyanines nanoparticles and calf thymus DNA was studied by UV–Vis and fluorescence spectroscopic method. The photocleavage DNA activities of three fluorinated dendritic silicon phthalocyanines nanoparticles were compared and the possible cleavage mechanism was proposed. Graphical abstract: Image 1 Highlights: Fluorinated and non-fluorinated silicon phthalocyanines with cyano/nitro/ester terminal groups was synthesized The photophysical properties of silicon phthalocyanines exhibited fluorinated substitution and terminal groups dependence. Fluorinated silicon phthalocyanines nanoparticles bind at the outside negative phosphate of DNA via "positive charge". MPEG@SiPc-F-COOCH3 showed the most outstanding photo-degradation ability through produce singlet oxygen.