Tetra-substituted phthalocyanines bearing thiazolidine derivatives: synthesis, anticancer activity on different cancer cell lines, and molecular docking studies
Date
5th OctobeMetadata
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aDepartment of Chemistry, Sakarya University, 54140Esentepe, Sakarya, Turkey. bCumhuriyet University, Faculty of Pharmacy, Department of Basic Pharmaceutical Sciences, Division of Biochemistry, Sivas, Turkey cPlant and Animal Production Department, Technical Sciences Vocational School of Sivas, Sivas Cumhuriyet University, 58140 Sivas, TurkeyAbstract
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.
