Evaluation of anti-cancer and anti-enzyme activities of imidazole derivative molecules with theoretical calculations

Cacan A. H., KARATAŞ H., TÜZÜN B., Taslimi P., Cacan E., KÖKBUDAK Z., ...Daha Fazla

Journal of Molecular Structure, cilt.1347, 2025 (SCI-Expanded, Scopus) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1347
  • Basım Tarihi: 2025
  • Doi Numarası: 10.1016/j.molstruc.2025.143264
  • 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: Anti-proliferative activity, Enzyme inhibition, Guanyl hydrazone, In silico analyses
  • Erciyes Üniversitesi Adresli: Evet

Özet

Nitrogen-containing heterocycles, known for their biological activity, were synthesized as four novel imidazole-based compounds via the reaction of guanyl hydrazones with 2-bromoacetyl naphthalene. The aim of this study was to synthesize and characterize these compounds and evaluate their potential as cholinesterase inhibitors and anticancer agents. Structural elucidation was performed using ¹H NMR, ¹³C NMR, FTIR, and MS. All compounds exhibited strong AChE and BChE inhibitory activities, with Ki values ranging from 131.44 to 415.54 nM (AChE) and 95.74 to 154.62 nM (BChE). IC₅₀ values confirmed potent inhibition. MTT assays demonstrated dose-dependent antiproliferative effects, with greater cytotoxicity observed in A2780 ovarian cancer cells than in MIA PaCa-2 pancreatic cells. In silico studies, including Gaussian (B3LYP, HF, M062X/6-31++G(d,p)), molecular docking, and ADME/T analyses, supported the pharmacological potential of these compounds. These findings highlight their promise as candidates for further development in cholinesterase inhibition and cancer therapy.