1-1-diphenyl-2-picrylhydrazyl and phthalocyanine

This study presents the preparation of a novel tetra-substituted phthalonitrile (1), namely, 3,6-bis(hexyloxy)-4,5-bis(4-(trifluoromethoxy)phenoxy)phthalonitrile (1) and its metal-free (2)/metal {M = Zn (3), Cu (4), Co (5), Lu(CH

Topics: Anti-Infective Agents; Antioxidants; Bacteria; Biofilms; Biphenyl Compounds; Candida parapsilosis; Candida tropicalis; Deoxyribonucleases; Halogenation; Isoindoles; Metals; Photochemotherapy; Photosensitizing Agents; Picrates; Singlet Oxygen

The emergence of nanoscience and its effect on the development of diverse scientific fields, particularly materials chemistry, are well known today. In this study, a new di-substituted phthalonitrile derivative, namely 4,5-bis((4-(dimethylamino)phenyl)ethynyl)phthalonitrile (1), and its octa-substituted metal phthalocyanines {M = Co (2), Zn (3)} were prepared. All the newly synthesized compounds were characterized using a number of spectroscopic approaches, including FT-IR, mass, NMR, and UV-vis spectroscopy. The resultant compounds modified the surface of the gold nanoparticles (NG-1-3). Characterization of the newly synthesized conjugates was carried out by transmission electron microscopy. The antioxidant activity of compounds 1-3, NG-1-3, and NG was evaluated using the DPPH scavenging process and the highest radical scavenging activity was obtained with compounds 1, NG-1, 2, and NG-2 (100%). The antimicrobial activity of compounds 1-3, NG-1-3, and NG was studied using a microdilution assay and the most effective antimicrobial activity was obtained for NG-3 against all the tested microorganisms. The newly synthesized compounds demonstrated high DNA cleavage activity. Compounds 1-3, NG-1-3, and NG significantly inhibited the microbial cell viability of

Topics: Anti-Bacterial Agents; Antioxidants; Biphenyl Compounds; Cell Survival; Coordination Complexes; Escherichia coli; Isoindoles; Metal Nanoparticles; Metals, Heavy; Microbial Sensitivity Tests; Picrates

This study presents the synthesis of a series of new tetra-substituted phthalocyanines bearing 3,5-bis(trifluoromethyl)phenoxy groups at non-peripheral positions. The resulting macromolecules were characterized by performing different spectroscopic methods including 1H NMR, UV-Vis, FT-IR, and mass spectroscopy. In this study, the synergistic effect of phthalocyanines used as colorants in ink formulas with other chemicals available was probed for the first time. The synergistic effect of methyl laurate on the biological and antioxidant activities of the compounds (2-5) was investigated. Moreover, the therapeutic properties of the complexes (3, 6, and 7) were investigated using photochemical methods. Upon comparison, complex 7 (ΦΔ = 0.42) was found to be more effective than complex 6 (ΦΔ = 0.40) and complex 3 (ΦΔ = 0.27) in terms of producing singlet oxygen. The results confirmed that the heavy atom effect improves the therapeutic effects.

Topics: Anti-Bacterial Agents; Antioxidants; Bacillus subtilis; Biphenyl Compounds; Coordination Complexes; Escherichia coli; Halogenation; Isoindoles; Microbial Sensitivity Tests; Molecular Structure; Photochemical Processes; Photosensitizing Agents; Picrates; Staphylococcus aureus

In this study, firstly, 3-(2,3-bis(hexadecylthio)propoxy)phthalonitrile (2) as a new phthalonitrile derivative was prepared. Then, new types of non-peripheral phthalocyanine derivatives [CuPc (3), ZnPc (4), and CoPc (5)] were synthesized by using this ligand. The synthesized new compounds were characterized by common spectroscopic methods such as FTIR, 1H-NMR, 13C-NMR, MALDI-TOF, UV-Vis and fluorescence spectroscopy. The H- or J-type aggregation behaviors of novel type metallophthalocyanines in the presence of valuable metal ions such as Ag(i) and Pd(ii) were investigated by UV-Vis and fluorescence spectroscopy. The quenching efficiency of the Ag(i) and Pd(ii) ions for ZnPc (4) was obtained using the Stern-Volmer equation and the quenching constant of ZnPc (4) towards Ag(i) and Pd(ii) ions was found to be 2.9 × 105 mol L-1 and 1.2 × 105 mol L-1, respectively. The binding constant (Ka) and binding stoichiometry (n) of Ag(i) and Pd(ii) ions for ZnPc (5) were calculated using a modified Benesi-Hildebrand equation, and were found to be 1.4 × 108 M-1 and 3.4 × 107 M-1, respectively. The binding ratio and free energy change of Ag(i) and Pd(ii) ions for ZnPc (4) were found to be 1.86, 1.54, -46.49 kJ mol-1 and -42.9 kJ mol-1, respectively. Also, the antioxidant properties of the synthesized novel type metallophthalocyanines and their Ag(i) and Pd(ii) ion doped aggregates were determined using three different methods: DPPH free radical scavenging activity, ferrous ion chelating activity and reducing power activity. Finally, the antibacterial and antifungal activities of phthalocyanine compounds synthesized within the scope of this study were determined by disc diffusion and macrobroth dilution methods and the effect of the doping of Ag(i) and Pd(ii) ions on the antibacterial activities of phthalocyanines was investigated.

Topics: Anti-Bacterial Agents; Antifungal Agents; Antioxidants; Bacillus subtilis; Biphenyl Compounds; Candida albicans; Escherichia coli; Fluorescence; Ions; Isoindoles; Microbial Sensitivity Tests; Palladium; Picrates; Silver; Staphylococcus aureus

The synthesis, characterization, spectral, antioxidant and antibacterial properties of dimethyl 5-(phenoxy)-isophthalate substituted Zinc, Cobalt, Copper, and Nickel phthalocyanines are reported. The novel compounds have been characterized by using electronic absorption, nuclear magnetic resonance spectroscopy, infrared, elemental analysis and mass spectrometry. The antioxidant and antibacterial activities of newly synthesized phthalocyanines and its starting material are tested. The DPPH free radical scavenging ability of phthalocyanine Co(II) and Zn(II) complexes on DPPH are 44.8% and 40.1% at 100 mg/L concentration, respectively. The phthalocyanine Co(II) and Cu(II) complexes show very strong ferrous ion chelating activity of 91.2% and 89.3% at concentration of 100 mg/L, respectively. Compound 3 displays strong reducing power like α-tocopherol. Antibacterial activities of phthalocyanine Co(II) and Amikacin (30 μg/disk) against Micrococcus luteus (ATCC 9341) are 16 mm in diameter.

Topics: Anti-Bacterial Agents; Antioxidants; Biphenyl Compounds; Chelating Agents; Free Radical Scavengers; Indoles; Isoindoles; Metals; Microbial Sensitivity Tests; Oxidation-Reduction; Phthalic Acids; Picrates; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization