Novel cobalt (II), zinc (II) phthalocyanines bearing discrete substituents: Synthesis, characterization, aggregation behavior, electrochemical properties and antioxidant activity

A new phthalonitrile derivative bearing 3,4,5-trimethoxybenzyloxy and chloro-substituents at peripheral position was prepared by a nucleophilic displacement reaction. Cyclotetramerization of phthalonitrile derivative in dimethylsulfoxide (DMSO) gave the metallophthalocyanines. Novel Co(II), Zn(II) phthalocyanines (Pcs) were obtained from the reaction 4-[(3,4,5- trimethoxybenzyloxy]-5-chlorophthalonitrile and metal salts. The novel compounds have been characterized by using elemental analysis, UV-Vis, FTIR, 1H-NMR spectral data. The aggregation behaviors of Co(II), Zn(II) Pcs were also investigated. These metallophthalocyanines do not show any aggregation behavior between 1.2 × 10−5 and 4.0 × 10−6Mconcentration range in DMF. The antioxidant activities of Pcs were investigated antioxidant assays such as free radical scavenging ability of 1,1-diphenyl-2-picryl-hydrazyl (DPPH) and ferrous ion chelating ability. Furthermore, the redox properties of the Pcs complexes were investigated by using cyclic voltammetry

Synthesis, Aggregation, Antioxidant and DNA-Binding Properties of Metallophthalocyanines Bearing 5-Tert-butyl-2-hydroxyphenoxy groups

In this study, the synthesis and characterization of new substituted metallophthalocyanines are described. A new phthalonitrile, 4-(5-tert-butyl-2-hydroxyphenoxy)-5-chlorophthalonitrile (3) was prepared. New compounds were characterized by UV–Vis, IR, 1HNMR, and elemental analysis. The aggregation behavior of the cobalt (II), magnesium (II) and copper (II) phthalocyanines were studied in tetrahydrofuran and in known concentration ranges. The antioxidant activities of compounds were evaluated. Their radical-scavenging capacity, metal chelating activity and reducing power was fully studied. The compound 3 showed 100% chelating activity as EDTA at concentration 50 mg/L. The DNA interaction of copper (II) phthalocyanine compound (6) was studied using UV/Vis titration, gel electrophoresis, cyclic voltammetry. The results indicated that compound 6 interacts with CT-DNA via intercalation binding mode

Synthesis and antioxidant, aggregation, and electronic properties of 6-tert-butyl-1,4-benzodioxine substituted phthalocyanines

As a starting material, 7-tert-butyldibenzo [b,e] [1,4] dioxine-2,3-dicarbonitrile was prepared by the reac- tion of 4-tert-butylcatechol with 4,5-dichlorophthalonitrile. Metallophthalocyanine complexes ( 4 { 7 ) were obtained by cyclotetramerization of 7-tert-butyldibenzo [b,e] [1,4] dioxine-2,3-dicarbonitrile. All compounds were characterized by elemental analysis and other spectroscopic methods (IR, UV/Vis, and 1 H NMR). Phthalocyanine compounds remained nonaggregated in tetrahydrofuran at the studied concentration ranges. Metallophthalocyanines ( 4 { 7 ) were tested for their antioxidant activities. The antioxidant activity processes included evaluation of radical-scavenging activity, chelat- ing activity, and reducing power. These compounds were compared to standard antioxidant ascorbic acid. The electronic data of the new compounds were obtained by computational calculations at the B3LYP/6-31G (d,p) level of theory

Co and Zn Metal Phthalocyanines with Bulky Substituents: Anticancer, Antibacterial Activities and Their Inhibitory Effects on Some Metabolic Enzymes with Molecular Docking Studies

WOS:000630387800001In this study, we reported the synthesis of new cobalt and zinc phthalocyanine compounds with ((ethylenediamine-N,N',N'-triacetic acid-N-2-ethyl)oxy) (ETAEO) substituted groups. Characterization studies and anticancer properties of both synthesized compounds were determined as well. The inhibitory effects of these complexes on some metabolic enzymes were examined and it was observed that the enzymes inhibited by complex molecules at the micromolar levels. In addition, the active sites of the enzymes were determined by molecular modeling programme for screening the enzyme-inhibitor interactions. The molecular docking method was used to calculate the interactions of molecules with enzymes. Also, human prostate and breast cancer cell lines (PC-3 and MCF-7) were used to determine the anticancer properties of the complexes. All doses of the tetrakis (ETAEO) phthalocyaninato Cobalt II (1) did not show any significant changes in PC-3 cell viability, but significantly reduced in MCF-7 cell viability. Similarly, all doses of the tetrakis (ETAEO) phthalocyaninato zinc II (2) significantly reduced MCF-7 cell viability compared to the control and solvent control groups. According to the enzyme inhibition studies, both complexes showed the best inhibition effects for alpha-Glycosidase enzyme with 125.85 +/- 30.35 mu M and 165.30 +/- 27.18 mu M Ki values