title: Silicon(IV) phthalocyanines substituted axially with different nucleoside moieties. Effects of nucleoside type on the photosensitizing efficiencies and in vitro photodynamic activities.
abstract: A series of new silicon(IV) phthalocyanines (SiPcs) di-substituted axially with different nucleoside moieties have been synthesized and evaluated for their singlet oxygen quantum yields (ΦΔ) and in vitro photodynamic activities. The adenosine-substituted SiPc shows a lower photosensitizing efficiency (ΦΔ=0.35) than the uridine- and cytidine-substituted analogs (ΦΔ=0.42-0.44), while the guanosine-substituted SiPc exhibits a weakest singlet oxygen generation efficiency with a ΦΔ value down to 0.03. On the other hand, replacing axial adenosines with chloro-modified adenosines and purines can result in the increase of photogenerating singlet oxygen efficiencies of SiPcs. The formed SiPcs 1 and 2, which contain monochloro-modified adenosines and dichloro-modified purines respectively, appear as efficient photosensitizers with ΦΔ of 0.42-0.44. Both compounds 1 and 2 present high photocytotoxicities against HepG2 and BGC823 cancer cells with IC50 values ranging from 9nM to 33nM. The photocytotoxicities of these two compounds are remarkably higher than the well-known anticancer photosensitizer, chlorin e6 (IC50=752nM against HepG2 cells) in the same condition. As revealed by confocal microscopy, for both cell lines, compound 1 can essentially bind to mitochondria, while compound 2 is just partially localized in mitochondria. In addition, the two compounds induce cell death of HepG2 cells likely through apoptosis.
authors.affiliation: College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou 350108, China.
authors.forename: Bi-Yuan
authors.initials: BY
authors.lastname: Zheng
authors.affiliation: College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou 350108, China.
authors.forename: Xiao-Min
authors.initials: XM
authors.lastname: Shen
authors.affiliation: College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou 350108, China.
authors.forename: Dong-Mei
authors.initials: DM
authors.lastname: Zhao
authors.affiliation: College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou 350108, China.
authors.forename: Yi-Bin
authors.initials: YB
authors.lastname: Cai
authors.affiliation: College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou 350108, China.
authors.forename: Mei-Rong
authors.initials: MR
authors.lastname: Ke
authors.affiliation: College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou 350108, China. Electronic address: jdhuang@fzu.edu.cn.
authors.forename: Jian-Dong
authors.initials: JD
authors.lastname: Huang
mesh_terms: D002460:Cell Line; D006801:Humans; D066298:In Vitro Techniques; D007211:Indoles / Q000737:chemistry / Q000494:pharmacology*; D054833:Isoindoles; D009705:Nucleosides / Q000737:chemistry*; D017319:Photosensitizing Agents / Q000737:chemistry / Q000494:pharmacology*; D066244:Proton Magnetic Resonance Spectroscopy; D012828:Silicones / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D007211:Indoles; D054833:Isoindoles; D009705:Nucleosides; D017319:Photosensitizing Agents; D012828:Silicones; C013647:phthalocyanine
keywords: Nucleoside; Photodynamic therapy; Photosensitizer; Silicon(IV) phthalocyanine; Singlet oxygen quantum yields