ABSTRACT
A novel zinc(II) phthalocyanine bearing octa-sulphonates has been prepared, which is non-aggregated in water, highly photoactive and low dark-toxic. More interestingly, it exhibits specific affinity to macrophages via the scavenger receptor-A, and can selectively accumulate in tumour sites.
Subject(s)
Indoles/therapeutic use , Macrophages/drug effects , Organometallic Compounds/therapeutic use , Photochemotherapy , Photosensitizing Agents/therapeutic use , Sulfonic Acids/therapeutic use , Animals , Cell Line , Cell Survival/drug effects , Dose-Response Relationship, Drug , Hep G2 Cells , Humans , Indoles/administration & dosage , Indoles/chemistry , Isoindoles , Macrophages/pathology , Mice , Mice, Nude , Molecular Structure , Neoplasms, Experimental/drug therapy , Neoplasms, Experimental/pathology , Organometallic Compounds/administration & dosage , Organometallic Compounds/chemistry , Photosensitizing Agents/administration & dosage , Photosensitizing Agents/chemistry , Structure-Activity Relationship , Sulfonic Acids/administration & dosage , Sulfonic Acids/chemistry , Zinc CompoundsABSTRACT
Two new tetra- or di-α-substituted zinc(II) phthalocyanines 5 and 6 have been prepared through a "side-strapped" method. In the molecules, the adjacent benzene rings of the phthalocyanine core are linked at α-position through a triethylene glycol bridge to form a hybrid aza-/oxa-crown ether. The tetra-α-substituted phthalocyanine 5 shows an eclipsed self-assembly property in CH2Cl2 and the effect on the di-α-substituted analogue 6 is significantly weakened. Furthermore, the crown ethers of these compounds can selectively complex with Fe(3+) or Cu(2+) ion in DMF, leading to formation of J-aggregated nano-assemblies, which can be disaggregated in the presence of some organic or inorganic ligands, such as triethylamine, tetramethylethylenediamine, CH3COO(-), or OH(-). In addition, both compounds are efficient singlet oxygen generators with the singlet oxygen quantum yields (Φ(Δ)) of 0.54-0.74 in DMF relative to unsubstituted zinc(II) phthalocyanine (Φ(Δ)=0.56). They exhibit photodynamic activities toward HepG2 human hepatocarcinoma cells, but the compound 6, which has more than 40-fold lower IC50 value (0.08 µM) compared to the analogue 5 (IC50=3.31 µM), shows remarkablely higher in vitro photocytotoxicity due to its significantly higher cellular uptake and singlet oxygen generation efficiency. The results suggest that these compounds can serve as promising multifunctional materials both in (opto)electronic field and photodynamic therapy.
