Synthesis, characterization, in vitro cholinesterase inhibition and cytotoxic activity of silicon(IV) phthalocyanines containing anthraquinone groups against lung and colorectal cancer cells

KELEŞ T., BIYIKLIOĞLU Z., Ali Y. A., AKKAYA D., YALÇIN C. Ö., BARUT B.

Journal of Molecular Structure, vol.1330, 2025 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 1330
  • Publication Date: 2025
  • Doi Number: 10.1016/j.molstruc.2025.141487
  • Journal Name: Journal of Molecular Structure
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Compendex, INSPEC
  • Keywords: Cholinesterases, Colorectal cancer, Cytotoxicity, Lung cancer, Phthalocyanine
  • Karadeniz Technical University Affiliated: Yes

Abstract

This study aimed to examine the synthesis, characterization, in vitro cholinesterase inhibition, and cytotoxic activity of silicon (IV) phthalocyanine containing anthraquinone groups against colorectal and lung cancer cells. First, 2-(3-hydroxypropoxy)anthra-9,10-quinone was obtained from the reaction of 2-hydroxyanthraquinone with 3‑chloro-1-propanol. Then, axially anthraquinone-substituted silicon phthalocyanines were synthesized by reacting SiPcCl2 with ANT-C3-OH and ANT-OH2. These phthalocyanines were characterized by using FT-IR, 1HNMR, 13CNMR, UV–vis, and mass spectra. Next, in vitro cholinesterase inhibition and cytotoxic activity of silicon (IV) phthalocyanine containing anthraquinone groups (ANT-C3-Si and ANT-OH2-Si) on human colorectal carcinoma (HCT-116) and human lung adenocarcinoma (A549) cells were investigated. Results showed that ANT-C3-Si exhibited greater AChE inhibition than ANT-OH2-Si, with IC50 value of 70.42 ± 2.50 µM. According to (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) analysis, ANT-C3-Si demonstrated higher cytotoxic effects in both cell lines after 24 h The study findings suggest that ANT-C3-Si has potential for use in Alzheimer's disease due to its lower IC₅₀ value and cytotoxic potential.