Design of N-heterocycle based-phthalonitrile/metal phthalocyanine-silver nanoconjugates for cancer therapies

• Published in: Dalton transactions : an international journal of inorganic chemistry 2023-09, Vol.52 (37), p.13119-13128
• Main Authors: Öney, Özlem psiz, Yenilmez, H. Yasemin, Bahar, Dilek, Öztürk, Nazl Farajzadeh, Altunta Bay r, Zehra
• Format: Article
• Language: English
• Subjects: Anticancer properties; Aqueous solutions; Biological properties; Cancer; Carbazoles; Irradiation; Metal phthalocyanines; Nanoparticles; NMR; Nuclear magnetic resonance; Silver; Synthesis
• ISSN: 1477-9226; 1477-9234
• DOI: 10.1039/d3dt01656k

This study reports the anticancer properties of carbazole-containing phthalonitrile/phthalocyanine-modified silver nanoparticles for the first time. In this study, a new mono-substituted phthalonitrile namely 3-[9 H -carbazole-9-ethoxy]phthalonitrile and its metal phthalocyanines {M = Zn, Co, and Mn(Cl)} were synthesized by template cyclotetramerization of phthalonitrile derivatives. The newly synthesized compounds were characterized using UV-vis, FT-IR, 1 H NMR, 13 C NMR, and mass spectroscopy. The resultant compounds were successfully linked to the surface of silver nanoparticles. The characterization of the surficial modification was carried out by applying the TEM technique. The cytotoxic activities of the studied nanoconjugates were tested against A549, DLD-1, and Wi38 cell lines by performing a (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) (MTT) assay with/without irradiation. Although the functionalization of silver nanoparticles increased the solubility of phthalocyanines in aqueous media, the presence of phthalonitrile/phthalocyanine derivatives on the silver nanoparticles' surface improved their biological properties. All the studied biological candidates exhibited antiproliferative activities against the cell lines. The IC 50 values calculated were between 6.80 and 97.99 μM against the studied cell lines in the dark. However, the IC 50 values determined were between 3.11 and 88.90 μM with irradiation. The highest IC 50 values obtained were 3.11 and 3.52 μM against the DLD-1 cell line for nanoconjugates 1-AgNP and 3-AgNP , respectively. The findings indicated that the compounds may be utilized as anticancer agents after further studies. The cytotoxic activities of the new phthalonitrile/metal phthalocyanine-nanoconjugates were tested against A549, DLD-1, and Wi38 cell lines using a (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) (MTT) assay with/without irradiation.