Synthesis and in Vitro Photodynamic Activity of Oligomeric Ethylene Glycol–Quinoline Substituted Zinc(II) Phthalocyanine Derivatives

Abstract

A new series of zinc(II) phthalocyanine derivatives have been synthesized and characterized. These macrocycles exhibited a sharp absorption band in the red visible region in DMF, which indicated that they were dissolved well and almost did not aggregate in this solvent. Compared with the unsubstituted zinc(II) phthalocyanine, all these phthalocyanines have a red-shifted Q-band (at 678-699 vs 670 nm) and exhibit a relatively weaker fluorescence emission and a higher efficiency at generating singlet oxygen. The monosubstituted photosensitizers also exhibit high photocytotoxicity toward HepG2 human hepatocarcinoma cells with IC50 values as low as 0.02-0.05 μM (λ = 670 nm, 80 mW·cm(-2), 1.5 J·cm(-2)). The high photodynamic activities of these compounds are in accordance with their low aggregation tendency and high cellular uptake. Their structure-activity relationship was assessed by determining the photophysical properties, cellular uptake, and in vitro photodynamic activities of this series of compounds. As shown by confocal microscopy, monosubstituted phthalocyanines can target the mitochondria and lysosomes of the cells, and tetrasubstituted phthalocyanines tend to target the lysosomes of the cells.

Spectroscopic analysis of the interaction between tetra-(p-sulfoazophenyl-4-aminosulfonyl)-substituted aluminum (III) phthalocyanines and serum albumins

“…It suggested that the AlPc mainly exist as dimer in water. 23,24 Remarkable changes in the Q band region were observed in the presence of BSA ( Fig. 2(a)) and HSA ( Fig.…”

Synthesis and in vitro Anticancer Activity of Zinc(II) Phthalocyanines Conjugated with Coumarin Derivatives for Dual Photodynamic and Chemotherapy

“…For these conjugates, zinc(II) phthalocyanine was used as the photosensitizing unit owing to its strong near-infrared absorption efficiency, high efficiency in generating singlet oxygen, and excellent photostability. [45,46] 7-Hydroxycoumarin or 7-hydroxy-4-trifluoromethylcoumarin were selected as the chemotherapeutic cytostatic portions. The two components were linked by a tri(ethylene glycol) chain, which enhances the amphiphilicity and biocompatibility of the system.…”

Molecular‐Target‐Based Anticancer Photosensitizer: Synthesis and in vitro Photodynamic Activity of Erlotinib–Zinc(II) Phthalocyanine Conjugates

“…[29] Over the past few years, we have been interested in developing efficient photosensitizers for PDT, especially zinc(II) phthalocyanine derivatives. [30,31] We recently reported two erlotinibzinc(II) phthalocyanine conjugates; erlotinib was chosen as the targeting moiety to conjugate with a zinc(II) phthalocyanine core at the a-position via an oligoethylene glycol spacer, which can improve the amphiphilicity and biocompatibility of the conjugate. By introduction of the erlotinib moiety, the two conjugates exhibited high specificity toward HepG2 cancer cells and A431 tumor tissues in nude mice.…”