Photophysicochemical and Biological Properties of New Phthalocyanines Bearing 4‐(trifluoromethoxy)phenoxy and 2‐(4‐methylthiazol‐5‐yl)ethoxy Groups on Peripheral Positions

Abstract

As thiazoles and fluorinated groups are well known as active species of hybrid pharmaceutical agents, this study aimed to evaluate the synergic effect of these groups on the biological features of phthalocyanines for the first time in the hope of discovering efficient pharmaceutical agents. Therefore, a new phthalonitrile derivative namely 4‐(2‐(4‐methylthiazol‐5‐yl)ethoxy)‐5‐(4‐(trifluoromethoxy)phenoxy)phthalonitrile (1) and its metal‐free (2)/metal phthalocyanines (3‐5) were prepared and characterized using various spectroscopic techniques. Solubility of new phthalocyanines (2‐5) was examined in a series of polar and nonpolar solvents. Additionally, sono/photochemical methods were applied to examine the photophysical and sono/photochemical properties of new zinc phthalocyanine to measure its potential as a probable material for sono/photodynamic therapies. The antioxidant activities of compounds (1‐5) were evaluated using the DPPH scavenging activity method and the highest radical scavenging activity was obtained 92.13% (200 mg L−1) for manganese phthalocyanine. All the phthalocyanines demonstrated high DNA nuclease activity, as well. The antimicrobial activities of compounds (1‐5) were investigated using disk diffusion and microdilution methods. The phthalocyanines exhibited effective microbial cell inhibition activity against Escherichia coli (E. coli). Antimicrobial photodynamic therapy activity was investigated against E. coli by LED irradiation. Compounds (2‐5) acted as photosynthesizers. Also, they displayed significant biofilm inhibition activity against Staphylococcus aureus (S. aureus) and Pseudomonas aeruginosa (P. aeruginosa).

Novel Graphene Oxide/Zinc Phthalocyanine Composites Bearing 3‐Chloro‐4‐Fluorophenoxy: Potential Usage for Sono/Photochemical Applications

“…When the results were compared, it was seen that all singlet oxygen yields increased significantly by sono‐photochemical studies compare to photochemical studies. ZnPc 2 has very high singlet oxygen quantum yield when compared to literatures including sono‐chemical studies for the Pc derivatives [33,34,54] . GO decorated phthalocyanine composite structures cannot be compared with previous studies due to lack of the literature on this field.…”

Anticancer activity of novel silicon phthalocyanines against the colorectal adenocarcinoma cell line (DLD-1)

“…50,51 The investigation of the DNA cleavage activity of different metal complexes such as metal phthalocyanines can help design novel advanced drugs, especially for the fight against cancers and bacteria. 52,53 In this study, stock samples of compounds (1-3-QSi) were prepared in DMSO and their pBR322 DNA cleavage activities were examined by performing agarose gel electrophoresis. The obtained results are shown in Fig.…”

The design and synthesis of metallophthalocyanine–gold nanoparticle hybrids as biological agents

“…Additionally, a wide range of metal ions can be inserted into the phthalocyanine cavity. [26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41] Some of the metal ions (with oxidation number Z 3) bearing axial ligands in a phthalocyanine cavity can shift the UV-vis spectra of phthalocyanines to near-IR/ IR regions and make the phthalocyanines suitable materials for electrochromic devices, 42 photodynamic therapy 43 (PDT), photovoltaic cells, 44 and photocatalytic systems. 45 All of these modifications reduce p-stacking interactions by increasing the distance between the phthalocyanine rings, which in turn results in the improvement of the phthalocyanines' solubility.…”

“…The formation of these isomeric mixtures and high dipole moments diminishes the p-stacking interactions. 30,35,36,38,50,51 Alkynes are essential functional groups that are extensively found in drugs, natural materials, and organic compounds. [52][53][54] Aromatic p-expanded materials are well-known as suitable materials in various applications including biology, molecular electronics, organic photovoltaic devices, pharmaceuticals, and sensing.…”