Tetra-substituted phthalocyanines bearing thiazolidine derivatives: synthesis, anticancer activity on different cancer cell lines, and molecular docking studies
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Date
2021Author
Bilgiçli, Ahmet T.Hepokur, Ceylan
Genc Bilgicli, Hayriye
Tüzün, Burak
Mısır, Sema
Zengina, Mustafa
Yarasir, M. Nilüfer
Günsel, Armağan
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Ahmet T. Bilgiçli, *a Ceylan Hepokur, b Hayriye Genc Bilgicli, a Burak Tüzün, c Armağan Günsel, a Sema Mısır,b Mustafa Zengina andAbstract
In the first step, (4R)-2-(2-hydroxyphenyl)thiazolidine-4-carboxylic acid (c) and 2-(2-(3,4-dicyano phenoxy)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 flu orescence 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 bio logical 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.