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

Özlem İpsiz Öney, H. Yasemin Yenilmez, Dilek Bahar, Nazlı Farajzadeh Öztürk, Zehra Altuntaş Bayır*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)


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-[9H-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, 1H NMR, 13C 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 IC50 values calculated were between 6.80 and 97.99 μM against the studied cell lines in the dark. However, the IC50 values determined were between 3.11 and 88.90 μM with irradiation. The highest IC50 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.

Original languageEnglish
Pages (from-to)13119-13128
Number of pages10
JournalDalton Transactions
Issue number37
Publication statusPublished - 4 Aug 2023

Bibliographical note

Publisher Copyright:
© 2023 The Royal Society of Chemistry.


Zehra Altuntaş Bayır appreciates the funding by the Research Fund of the Istanbul Technical University (Project Number: TDK-2022-43617).

FundersFunder number
Istanbul Teknik ÜniversitesiTDK-2022-43617


    Dive into the research topics of 'Design of N-heterocycle based-phthalonitrile/metal phthalocyanine-silver nanoconjugates for cancer therapies'. Together they form a unique fingerprint.

    Cite this