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, cilt.1330, 2025 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1330
  • Basım Tarihi: 2025
  • Doi Numarası: 10.1016/j.molstruc.2025.141487
  • Dergi Adı: Journal of Molecular Structure
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Compendex, INSPEC
  • Anahtar Kelimeler: Cholinesterases, Colorectal cancer, Cytotoxicity, Lung cancer, Phthalocyanine
  • Karadeniz Teknik Üniversitesi Adresli: Evet

Özet

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.