Octa‐substituted Zinc(II), Cu(II), and Co(II) phthalocyanines with 1‐(4‐hydroxyphenyl)propane‐1‐one: Synthesis, sensitive protonation behaviors, Ag(I) induced H‐type aggregation properties, antibacterial–antioxidant activity, and molecular docking studies

Abstract

This study shows the synthesis and characterization of 4,5-bis(4-propionylphenoxy)phthalonitrile (2) and its octa-substituted phthalocyanine derivatives [ZnPc(3), CuPc(4), and CoPc(5)]. A combination of standard spectroscopic techniques has characterized the newly synthesized phthalonitrile derivative and phthalocyanines. The aggregation behaviors of new octa-substituted phthalocyanines have been evaluated by ultravioletvisible (UV-vis) spectroscopy. The metal ion-sensitive behaviors of new octa-substituted phthalocyanines in the presence of soft metal ions have been performed by UV-vis and fluorescence spectrophotometer. The quenching efficiency (K sv ) of Ag + ions against ZnPc(3) was found using the Stern-Volmer equation. The binding constant (K a ) and binding stoichiometry (n) of ZnPc(3) with Ag + ions were calculated using the modified Benesi-Hildebrand equation. Sensitive protonation behaviors of octa-substituted phthalocyanines have been investigated by titration experiments as well as computational calculations. The ZnPc(3) and CuPc(4) were exhibited H-type aggregation behaviors toward Ag + ions. However, the protonation of octa-substituted zinc and copper phthalocyanine during the titration with HCl caused J-type selfaggregation properties. In vitro antioxidant properties of the new compounds were investigated by the radical scavenging ability of 1,1-diphenyl-2-picrylhydrazyl (DPPH), chelating ability to ferrous ions, and reducing power methods. Additionally, in vitro antibacterial activities of the octa-substituted phthalocyanines were determined. Finally, optimized structures of novel compounds [(2), ZnPc(3), CuPc(4), and CoPc(5)] were obtained on the HF (Hartree-Fock), B3LYP (Becke, 3-parameter, Lee-Yang-Parr), M06-2X methods with 3-21 g, 6-31 g and SDD basis set. Then, biological activities of

Synthesis, Molecular Docking and Antiproliferative Activity Studies of a Thiazole‐Based Compound Linked to Hydrazone Moiety

“…In Figure 6b, it was observed that hydrogen bond interaction occurs between the nitrogen atom in the nitrobenzene group in the molecule and the ASP 55 protein. In the calculations made, it is expected that the active points of the molecules will interact with ASP 55, GLN 35, GLN 44, and TYR 36 [37] . In Figure 6c, it is seen that the oxygen atom attached to the carboxyl group next to the thiazolidine ring in the molecule makes hydrogen bonds with the ASN 209 protein.…”

“…In the calculations made, it is expected that the active points of the molecules will interact with ASP 55, GLN 35, GLN 44, and TYR 36. [37] In Figure 6c, it is seen that the…”

The Evaluation of Anticancer, Antioxidant, Antidiabetic and Anticholinergic Potentials of Endemic Rhabdosciadium microcalycinum Supported by Molecular Docking Study

“…The molecule with the highest interaction of molecules with anti‐oxidant and enzyme proteins has the most negative docking score value. Chemical interactions that occur between molecules and proteins are hydrogen bonds, polar and hydrophobic interactions, π‐π and halogen [40–44] . These interactions of molecules in RM with anti‐oxidant and enzyme proteins are given in Figures 6, 7, 8, 9, and 10.…”

“…Chemical interactions that occur between molecules and proteins are hydrogen bonds, polar and hydrophobic interactions, π-π and halogen. [40][41][42][43][44] These interactions of molecules in RM with anti-oxidant and enzyme proteins are given in Figures 6, 7, 8, 9, and 10.…”

Quinoline‐fused both non‐peripheral and peripheral ZnIIand MgIIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

“…When the interactions of CN p /CN np , ZnPc p /ZnPc np , and MgPc p /MgPc np with cancer proteins were examined, comparisons to E total energy values were made. [ 73 ] In the calculations made, it was seen that the biological activity of the phthalonitrile derivatives was lower than that of the metallated phthalocyanine compounds. However, for a more detailed analysis, chemical interaction was revealed by PLIP analysis.…”