Synthesis of (4R)-2-(3-hydroxyphenyl)thiazolidine 4-carboxylic acid substituted phthalocyanines: Anticancer activity on different cancer cell lines and molecular docking studies
Date
2021Metadata
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Ahmet T. Bilgiçli1 | Hayriye Genc Bilgicli1 | Ceylan Hepokur2 | Burak Tüzün3 | Arma gan Günsel1 | Mustafa Zengin1 | M. Nilüfer Yarasir1 1Department of Chemistry, Sakarya University, Serdivan, Turkey 2Department of Basic Pharmaceutical Sciences, Division of Biochemistry, Faculty of Pharmacy, Sivas Cumhuriyet University, Sivas, Turkey 3Department of Chemistry, Sivas Cumhuriyet University, Sivas, TurkeyAbstract
In this study, firstly, (4R)-2-(3-hydroxyphenyl)thiazolidine-4-carboxylic acid (1)
and (4R)-2-(3-(3,4-dicyanophenoxy)phenyl)thiazolidine-4-carboxylic acid (2)
were prepared. Then, the novel type metallophthalocyanines (ZnPc (3), CuPc
(4), and CoPc (5)) bearing thiazolidine groups in peripheral positions were syn thesized using by compound (2). The synthesized new compounds (1–5) were
characterized by the combination of standard spectroscopic methods such as
FT-IR, 1
H NMR, 13C NMR, UV–Vis spectral data, and MALDI-TOF. Aggrega tion behaviors of peripheral tetra-substituted metallophthalocyanines were
investigated in dimethyl sulfoxide (DMSO) media. Fluorescence properties and
fluorescence quantum yield of the new type zinc phthalocyanine (3) were per formed in DMSO at room temperature. The anticancer activity of novel type
metallophthalocyanines bearing thiazolidine groups in peripheral positions were
investigated on rat glioma cancer (C6), human prostate carcinoma (DU-145),
and normal human lung fibroblast (WI-38) cell lines. Finally, the biological and
chemical activities of (4R)-2-(3-(3,4-dicyanophenoxy)phenyl)thiazolidine 4-carboxylic acid (2) and its novel type metallophthalocyanines (ZnPc (3), CuPc
(4), and CoPc (5)) have been compared with many parameters obtained using
theoretical methods that are the Gaussian software and molecular docking.
