Biological Performance of Hexadeca-Substituted Metal Phthalocyanine/Reduced Graphene Oxide Nanobioagents.

This study presents a tetra-substituted phthalonitrile derivative, namely, diethyl 2-(3,4-dicyano-2,5-bis(hexyloxy)-6-(4-(trifluoromethoxy)phenoxy)phenyl)malonate (a), cyclotetramerizing in the presence of some metal salts. The resultant hexadeca-substituted metal phthalocyanines [M= Co, Zn, InCl)] (b-d) were used for the modification of reduced graphene oxide for the first time. The effect of the phthalonitrile/metal phthalocyanines on biological features of reduced graphene oxide (rGO) was extensively examined by the investigation of antioxidant, antimicrobial, DNA cleavage, cell viability, and antibiofilm activities of nanobioagents (1-4). The results were compared with those of unmodified rGO (nanobioagent 5), as well. Modification of reduced graphene oxide with the synthesized compounds improved its antioxidant activity. The antioxidant activities of all the tested nanobioagents also enhanced as the concentration increased. The antibacterial activities of all the nanobioagents improved by applying the photodynamic therapeutic (PDT) method. All the phthalonitrile/phthalocyanine-based nanobioagents (especially phthalocyanine-based nanocomposites) exhibited DNA cleavage activities, and complete DNA fragmentation was observed for nanobioagents (1-4) at 200 mg/L. They can be used as potent antimicrobial and antimicrobial photodynamic therapy agents as well as Escherichia coli microbial cell inhibitors. As a result, the prepared nanocomposites can be considered promising candidates for biomedicine.

Antibacterial and antioxidant activity of gold and silver nanoparticles in dextran-polyacrylamide copolymers.

Search for new antimicrobial agents is of great significance due to the issue of antimicrobial resistance, which nowadays has become more important than many diseases. The aim of this study was to evaluate the toxicity and biological effects of a dextran-graft-polyacrylamide (D-PAA) polymer-nanocarrier with/without silver or gold nanoparticles (AgNPs/D-PAA and AuNPs/D-PAA, respectively) to analyze their potential to replace or supplement conventional antibiotic therapy. The toxicity of nanocomplexes against eukaryotic cells was assessed on primary dermal fibroblasts using scratch, micronucleus and proliferation assays. DPPH (2,2-diphenyl-1-picrylhydrazylradical) assay was used to evaluate the antioxidant capacity of D-PAA, AgNPs/D-PAA and AuNPs/D-PAA. DNA cleavage, antimicrobial and biofilm inhibition effects of nanocomplexes were investigated. Nanocomplexes were found to be of moderate toxicity against fibroblasts with no genotoxicity observed. AgNPs/D-PAA reduced motility and proliferation at lower concentrations compared with the other studied nanomaterials. AgNPs/D-PAA and AuNPs/D-PAA showed radical scavenging capacities in a dose-dependent manner. The antimicrobial activity of AgNPs/D-PAA against various bacteria was found to be much higher compared to D-PAA and AuNPs/D-PAA, especially against E. hirae, E. faecalis and S. aureus, respectively. D-PAA, AgNPs/D-PAA and AuNPs/D-PAA showed DNA-cleaving and biofilm inhibitory activity, while AgNPs/D-PAA displayed the highest anti-biofilm activity. AgNPs/D-PAA and AuNPs/D-PAA were characterized by good antimicrobial activity. According to the findings of the study, AgNPs/D-PAA and AuNPs/D-PAA can be evaluated as alternatives for the preparation of new antimicrobial agents, the fight against biofilms, sterilization and disinfection processes. Our findings confirm the versatility of nanosystems based on dextran-polyacrylamide polymers and indicate that AgNPs/D-PAA and AuNPs/D-PAA can be evaluated as alternatives for the preparation of novel antimicrobial agents.

Synthesis and characterization of novel BODIPYs and their antioxidant, antimicrobial, photodynamic antimicrobial, antibiofilm and DNA interaction activities.

In the current study, we synthesized and characterized new BODIPY derivatives (1-4) having pyridine or thienyl-pyridine substituents at meso- position and 4-dibenzothienyl or benzo[b]thien-2-yl moieties at 2-,6- positions. We investigated fluorescence properties and the ability to form singlet oxygen. In addition, various biological activities of BODIPYs such as DPPH scavenging, DNA binding/cleavage ability, cell viability inhibition, antimicrobial activity, antimicrobial photodynamic therapy (aPDT) and biofilm inhibition properties were performed. BODIPY derivatives BDPY-3 (3) and BDPY-4 (4) have high fluorescence quantum yields as 0.50 and 0.61 and 1 O2 quantum yields were calculated as 0.83 for BDPY-1 (1), 0.12 for BDPY-2 (2), 0.11 for BDPY-3 and 0.23 for BDPY-4. BODIPY derivatives BDPY-2, BDPY-3 and BDPY-4 displayed 92.54 ± 5.41%, 94.20 ± 5.50%, and 95.03 ± 5.54% antioxidant ability, respectively. BODIPY compounds showed excellent DNA chemical nuclease activity. BDPY-2, BDPY-3 and BDPY-4 also exhibited 100% APDT activity against E. coli at all tested concentrations. In addition to these, they demonstrated a highly effective biofilm inhibition activity against Staphyloccous aureus and Pseudomans aeruginosa. BDPY-4 showed the most effective antioxidant and DNA cleavage activity, while BDPY-3 exhibited the most effective antimicrobial and antibiofilm activity.

Effect of Axial Ligand Length on Biological and Anticancer Properties of Axially Disubstituted Silicon Phthalocyanines.

In this study, three new axially disubstituted silicon phthalocyanines (SiPc1-3) and their quaternized phthalocyanine derivatives (QSiPc1-3) were prepared and characterized. The biological properties (antioxidant, antimicrobial, antibiofilm, and microbial cell viability activities) of the water-soluble silicon phthalocyanines were examined, as well. A 1 % DMSO diluted with pure water was used as a solvent in biological activity studies. All the compounds exhibited high antioxidant activity. They displayed efficient antimicrobial and antimicrobial photodynamic therapeutic properties against various microorganisms, especially Gram (+) bacteria. Additionally, they demonstrated high antibiofilm activities against S. aureus and P. aeruginosa. In addition, 100 % bacterial reduction was obtained for all the studied phthalocyanines against E. coli viable cells. Besides, the DNA cleavage and binding features of compounds (QSiPc1-3) were studied using pBR322 DNA and CT-DNA, respectively. Furthermore, the human topoisomerase I enzyme inhibition activities of compounds QSiPc1-3 were studied. Anticancer properties of the water-soluble compounds were investigated using cell proliferation MTT assay. They exhibited anticarcinogenic activity against the human colon cancer cell line (DLD-1). Compounds QSiPc1 and QSiPc3 displayed a high anticarcinogenic effect on the DLD-1 cell line. The obtained results indicated that all the studied compounds may be effective biological agents and anticancer drugs after further investigations.

Antimicrobial and antioxidant activity of phenolic extracts from walnut (Juglans regia L.) green husk by using pressure-driven membrane process.

In this study, antioxidant (DPPH and metal chelating), DNA cleavage, biofilm, and antimicrobial properties of extracted phenol from the walnut green husk (WGH) and its different concentrate and permeate samples were evaluated. For maximum phenolic compound extraction from the WGH first, the effects of solvent type (deionized water, methanol, n-hexane, acetone, and ethanol), solvent temperature (25-75 °C), and extraction time (0.5-24 h) were optimized. Then to concentrate phenolic compounds a pressure-driven membrane process was used with four different membrane types. The phenol contents of the concentrate samples were found to be microfiltration (MF) concentrate 4400 mg/L, ultrafiltration (UF) concentrate 4175 mg/L, nanofiltration (NF) concentrate 8155 mg/L, and reverse osmosis (RO) concentrate 8100 mg/L. LC-MSMS was used to determine the quantification of phenolic compounds in permeate and concentrate streams. In addition, all of the concentrate samples with high phenol content showed a high antioxidant activity as 100% with MF concentrate, UF concentrate, NF concentrated and RO concentrated. Likewise, concentrate samples were found to have very high antibiofilm activity as 82.86% for NF concentrate againts S. aureus, 85.80% for NF concentrate against P. aureginosa, 80.95% for RO concentrate against S. aureus, and 83.61% for RO-concentrate against P. aureginosa. When the antimicrobial activity of the extracted phenol from WGH and its different concentrate and permeate samples were evaluated by micro dilution and disk diffusion methods, it was found that the ability of the concentrate samples to inhibit bacterial growth was much higher than permeate ones. In addition, extracted phenol from WGH and its different concentrate and permeate samples showed significant DNA nuclease activity. Supplementary Information: The online version contains supplementary material available at 10.1007/s13197-022-05588-w.

Biological properties of hexadeca-substituted metal phthalocyanines bearing different functional groups.

In this study, a new tetra-substituted phthalonitrile (diethyl 2-(2-chloro-4,5-dicyano-3,6-bis(hexyloxy)phenyl)malonate) bearing three different substituents was synthesized and characterized. Due to the basic medium, transesterification occurred during the synthesis of the target phthalocyanines [M = Zn (II), Cu (II), Co (II), In (III), Lu (III)] in n-pentanol and the ethyl groups were replaced with pentyl groups. The biological features of the resultant compounds were studied for the first time in this study. All the compounds exhibited high antioxidant, antimicrobial, and DNA cleavage activities. The highest antioxidant activity was obtained 90.39% for lutetium phthalocyanine at 100 mg/L. The most effective MIC value was obtained 8 mg/L against Candida parapisilosis. The most effective microbial cell viability inhibition was obtained 100% for cobalt and lutetium phthalocyanines. They exhibited excellent biofilm inhibiton activities. Higher biofilm inhibition was achieved using light irradiation. The compounds exhibited higher biofilm inhibition activities with photodynamic against Staphylococcus aureus compared with Pseudo aureginosa.

Synthesis of two different zinc oxide nanoflowers and comparison of antioxidant and photocatalytic activity.

Nanoflowers are a newly developed class of nanoparticles that show flower-like structures and attract much attention due to their simple preparation methods, high stability, and increased efficiency. The aim of the study is to investigate a strong alternative to reduce the severity of infection and increase the treatment of wastewater by exhibiting biofilm inhibition in medical and environmental applications of the ZnO-NFs with two different shapes. ZnO-NFs were synthesized by two different processes hydrothermal method (named ZnO-NF1) and the precipitation method (named ZnO-NF2). ZnO-NFs produced by two different synthesis methods were compared for the photocatalytic and antioxidant efficiency. The effects of Reactive Red 180 (RR180) and Basic Red 18 (BR18) dyes concentration, photocatalyst amount, and reaction time were investigated on dye removal efficiency for photocatalytic experiments. The color was completely removed for 25 mg/L BR18 and RR180 dyes for 75 min and 90 min, respectively, using 1.5 g/L photocatalyst amount using ZnO-NF1. However, 59.18% dye removal efficiency was obtained for 90 min by using a 1.5 g/L ZnO-NF2 photocatalyst for 25 mg/L BR18 dye removal, while a dye removal efficiency of 90.00% was detected for 90 min using 2 g/L ZnO-NF2 for 25 mg/L RR180 dye. Then, comparison of general properties such as antibacterial, antibiofilm, microbial cell viability, DNA fragmentation, antioxidant activities, and antimicrobial photodynamic therapy of ZnO-NFs were investigated. The antioxidant activity of ZnO-NF2 was found to be higher than ZnO-NF1 at each concentration (82.32% and 87.18% for ZnO-NF1 and ZnO-NF2, respectively, at 200 mg/mL).