Tetra-substituted phthalocyanines bearing thiazolidine derivatives: synthesis, anticancer activity on different cancer cell lines, and molecular docking studies

Abstract

In the first step, (4R)-2-(2-hydroxyphenyl)thiazolidine-4-carboxylic acid (c) and 2-(2-(3,4-dicyanophenoxy)phenyl)thiazolidine-4-carboxylic acid (1) were prepared. Then, the peripherally tetra-substituted metallophthalocyanines [ZnPc (2), CuPc (3), and CoPc (4)] were synthesized by using 1. The structures of the obtained compounds were characterized by common spectroscopic methods. Aggregation behaviors of the tetra-substituted metallophthalocyanines (2–4) were investigated by UV-Vis and fluorescence spectroscopy in the presence/absence of soft metal ions. The electronic spectra of the newly synthesized metallophthalocyanines [ZnPc (2), CuPc (3), and CoPc (4)] were analyzed by the Bayliss method. The fluorescence quantum yield of diamagnetic ZnPc (2) was obtained in DMSO at room temperature. Also, the anticancer activity of the newly synthesized metallophthalocyanine derivatives was studied on C6, DU-145, and WI-38 cell lines and investigated using six concentrations (3.125; 6.25; 12.5; 50; 75; 100 μg L⁻¹). The cell cycle and apoptosis analyses of CuPc (3) were performed. In addition, the chemical and biological activities of 2-(2-(3,4-dicyanophenoxy)phenyl)thiazolidine-4-carboxylic acid (1) and its novel type metallophthalocyanines [ZnPc (2), CuPc (3), and CoPc (4)] were compared with many parameters obtained from the Gaussian software and molecular docking methods.