Glycerol group substituted bis(2-pyridylimino)isoindoline (BPI) complexes: synthesis, characterization and investigation of their biological properties.

In this study, a glycerol group substituted bis(2-pyridylamino)isoindoline (BPI-OH) ligand and its metal complexes (M = Pt, Cu and Co) were synthesized. Characterization of all new compounds was carried out using FT-IR, NMR, UV-Vis, and mass spectroscopy. Various biological activities of BPI derivatives were also tested. The antioxidant activities of BPI-OH, Pt-BPI-OH, Cu-BPI-OH, and Co-BPI-OH were 87.52 ± 4.62%, 98.05 ± 5.61%, 92.20 ± 5.12%, and 89.27 ± 4.74%, at 200 mg L-1 concentration respectively. BPI derivatives displayed perfect DNA cleavage activity and plasmid DNA was completely broken at all tested concentrations. The antimicrobial and antimicrobial photodynamic therapy (APDT) activities of the compounds were investigated and BPI derivatives showed good APDT. E. coli cell viability was inhibited at 125 and 250 mg L-1. BPI-OH, Pt-BPI-OH, Cu-BPI-OH, and Co-BPI-OH also successfully inhibited the biofilm formation of S. aureus and P. aeruginosa. Furthermore, the antidiabetic activity of BPI derivatives was studied. This study also evaluates the binding affinities of four compounds (BPI-OH, Pt-BPI-OH, Cu-BPI-OH, and Co-BPI-OH) to various residues of DNA using hydrogen bond distance measurements and binding energies. The results show that the BPI-OH compound forms hydrogen bonds with residues in the major groove of DNA, while BPI-Pt-OH, BPI-Cu-OH, and BPI-Co-OH compounds form hydrogen bonds with residues in the minor groove. The hydrogen bond distances for each compound range from 1.75 to 2.2 Angstroms.

Synthesis, fabrication and characterization of 2-naphthyloxy group-substituted bis(2-pyridylimino)isoindoline and its derivatives as a positive electrode for vanadium redox flow battery applications.

In recent years, tridentate nitrogen donor ligands have played a vital role in inorganic chemistry. The ease of synthesis, readily modifiable structure and high stability of 1,3-bis(2-pyridylimino)isoindole (BPIs) compounds make them suitable candidates for many potential applications. In this study, a 1,3-bis(2-pyridylimino)isoindoline derivative bearing a naphthoxy unit and its palladium complex (PdBPI) were synthesized and characterized by single crystal X-ray diffraction, NMR, FT-IR, UV-Vis, and mass spectroscopic methods. The BPI- or PdBPI-modified pencil graphite electrodes were clarified via cyclic voltammetry (CV), electrochemical impedance spectroscopy (EIS), scanning electron microscopy (SEM), EDX, X-ray photoelectron spectroscopy (XPS) and Raman spectroscopy. The efficiency of these substances in a vanadium redox flow battery (VRB) system was investigated for the first time. The behaviors of the BPI-modified carbon felt electrode (BPI-CF) and PdBPI-modified carbon felt electrode (PdBPI-CF) were investigated in the redox flow battery (RFB) applications. These modified electrodes were obtained by the electrodeposition method. The respective charge potentials of BPI-CF and PdBPI-CF reached 1.63 V and 1.88 V, respectively. The discharge capacity maxima obtained were ∼301 mA h (1204 mA h L-1) and ∼303 mA h (1212 mA h L-1) for BPI-CF and PdBPI-CF at the VRB system under a charge current density of 4.0 mA cm-2 and discharge current density of 0.4 mA cm-2, respectively.

Comparatively sonophotochemical and photochemical studies of phthalocyanines with cationic substituents on nonperipheral positions.

The term sonophotodynamic therapy (SPDT) refers to a combination of sonodynamic therapy (SDT) and photodynamic therapy (PDT), in which the efficacy of the treatment is boosted by utilizing the proper amount of a sensitizer that is responsive to both light and ultrasound. Although it has been proven in photophysicochemical studies that SPDT enhances singlet oxygen production, related studies in the literature are very limited. Considering this situation, this study aims to investigate the efficacy of synthesized phthalocyanines in terms of PDT and SPDT. The singlet oxygen quantum values calculated as 0.13 for 5, 0.44 for 6, and 0.61 for 7 in photochemical (PDT) application increased to 0.18, 0.86, and 0.92, respectively, with sonophotochemical (SPDT) application. According to the results, singlet oxygen production was more efficient with SPDT. This work will add to the body of knowledge on employing the SPDT approach to increase singlet oxygen generation.

Pegylated metal-free and zinc(II) phthalocyanines: synthesis, photophysicochemical properties and in vitro photodynamic activities against head, neck and colon cancer cell lines.

In this study, a series of peripherally and non-peripherally tetra-substituted metal-free and zinc(II) phthalocyanines were successfully prepared in good yields by cyclotetramerization of the phthalonitrile derivative bearing a tetraethylene glycol methyl ether group at 3- and 4- positions. All newly synthesized compounds were characterized using spectroscopic methods, such as FT-IR, NMR, mass and UV-Vis spectroscopy. To determine the therapeutic potential of the synthesized phthalocyanines, the effects of the substitution pattern (peripheral and non-peripheral) and central metal atom on the photophysicochemical properties were investigated. When comparing their singlet oxygen generation capabilities (ΦΔ), metallo-phthalocyanine derivatives with zinc (0.73 for 1b and 0.70 for 2b) showed higher singlet oxygen yield than metal-free derivatives (0.21 for 1a and 0.12 for 2a) in DMSO. The photodynamic therapy activities of the water-soluble phthalocyanines were tested via in vitro studies using the A253, FaDu (head and neck cancer cell lines), and HT29 (colon cancer) cell lines. The strongest photodynamic activity was found in 1b and 2b molecules with a metal core among the four molecules studied. The results suggested that the non-peripherally tetra-substituted 1b molecule was regarded as a suitable photodynamic therapy agent due to its light cytotoxicity and secondary impact induced by ROS production.

In-situ synthesis of phthalocyanines on electrospun TiO2 nanofiber by solvothermal process for photocatalytic degradation of methylene blue.

Titanium dioxide/phthalocyanine (TiO2/Pc), TiO2/fluor containing phthalocyanine (TiO2/FPc), and TiO2/fluor containing cobalt phthalocyanine (TiO2/FCoPc) had been successfully fabricated by a simple combination of phthalocyanines obtained by in-situ synthesis on the surface of TiO2 nanofibers prepared by electrospinning. Scanning electron microscopy micrographs and X-ray diffraction analysis indicated that the phthalocyanines uniformly immobilized on the surface of TiO2 nanofibers. Photocatalytic activity of TiO2, TiO2/Pc, TiO2/FPc, TiO2/FCoPc nanofibers for methylene blue in water was comparatively investigated firstly by ultraviolet-visible absorption measurements with time, and kinetic parameters were calculated. Results indicated that the obtained TiO2/Pc, TiO2/ FPc and TiO2/FCoPc exhibited high photocatalytic activity for the degradation of methylene blue and TiO2/FCoPc was found the best. It showed similar or higher activities than related studies and can be suggested as a promising candidate for environmental and energy applications.