Biomedical and computational exploration of rationally designed ciprofloxacin tethered β-amino alcohols as anti-cancer agents

Akhtar R., MUHAMMED M. T., Rasul A., Zahoor A. F., Noreen R., Tabassum H., ...Daha Fazla

Journal of Molecular Structure, cilt.1340, 2025 (SCI-Expanded, Scopus)

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1340
  • Basım Tarihi: 2025
  • Doi Numarası: 10.1016/j.molstruc.2025.142592
  • 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 A549, anti Hep-G2, Ciprofloxacin, DFT studies, in silico modeling, MD simulations, β-amino alcohols
  • Süleyman Demirel Üniversitesi Adresli: Evet

Özet

To explore the biological potential of ciprofloxacin-endowed derivatives, herein, we have outlined the synthesis, in vitro and in silico anti-proliferative assessment of a catalog of ciprofloxacin-based β-amino alcohols (3a–h) by using computer-aided drug design (CADD) and MTT assay. The targeted ciprofloxacin derivatives were accessed in good to efficient yields (70–85 %) by the ring opening of substituted epoxides with ciprofloxacin ester (employed as N-nucleophile). The characterization of the synthesized derivatives was accomplished through spectroscopic techniques followed by their in vitro cytotoxic evaluation against the liver cancer cell line (Hep-G2) and lung cancer cell line (A549). The majority of the synthesized ciprofloxacin-based beta-amino alcohols demonstrated noteworthy anti-cancer activities. Particularly, compound 3b emerged as the most promising anticancer agent with 11.35 ± 0.59 % cell viability against the Hep-G2 cell line, and 19.08 ± 0.34 % cell viability against the A549 cell line in comparison with standard reference drugs. DFT studies and the in silico molecular docking studies provided insights into the reactivity of the most bioactive molecule 3b. Moreover, MD simulations results were also found to be in agreement with in vitro findings which validated the anticancer therapeutic efficacy of the compound 3b