Synthesis, biological evaluation and molecular docking studies of bis-chalcone derivatives as xanthine oxidase inhibitors and anticancer agents

Burmaoglu S., Ozcan S., Balcioglu S., Gencel M., Noma S. A. A., EŞSİZ GÖKHAN Ş., ...Daha Fazla

BIOORGANIC CHEMISTRY, cilt.91, 2019 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 91
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1016/j.bioorg.2019.103149
  • Dergi Adı: BIOORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Anahtar Kelimeler: Bis-chalcone, Synthesis, Claisen-Schmidt condensation, Inhibition, Cytotoxicity, FLUORINE, BINDING, DESIGN, FORM
  • İnönü Üniversitesi Adresli: Evet

Özet

In this study, a series of B-ring fluoro substituted bis-chalcone derivatives were synthesized by Claisen-Schmidt condensation reactions and evaluated for their ability to inhibit xanthine oxidase (XO) and growth inhibitory activity against MCF-7 and Caco-2 human cancer cell lines, in vitro. According to the results obtained, the bis-chalcone with fluoro group at the 2 (4b) or 2,5-position (4g) of B-ring were found to be potent inhibitors of the enzyme with IC50 values in the low micromolar range. The effects of these compounds were about 7 fold higher than allopurinol. The binding modes of the bis-chalcone derivatives in the active site of xanthine oxidase were explained using molecular docking calculations. Also, compound 4g and 4h showed in vitro growth inhibitory activity against a panel of two human cancer cell lines 1.9 and 6.8 mu M of IC50 values, respectively.