Synthesis of bioactive quercetin-boronate esters as a novel biological agent: Enzyme inhibition, anti-microbial properties, computational insights and anti-cancer activity


Yildirim M., Kilic A., Cimentepe M., Necip A., Turedi S.

Journal of Molecular Structure, cilt.1321, 2025 (SCI-Expanded, Scopus) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1321
  • Basım Tarihi: 2025
  • Doi Numarası: 10.1016/j.molstruc.2024.140216
  • Dergi Adı: Journal of Molecular Structure
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Chimica, Compendex, INSPEC
  • Anahtar Kelimeler: Anti-cancer activity, Antimicrobial studies, Boronate ester, Enzyme inhibition, Quercetin, Spectroscopy
  • Çukurova Üniversitesi Adresli: Hayır

Özet

This study introduces a novel synthesis for the quercetin-boronate esters (QB1-QB4) for some biological applications. The structure of low-cost, easily synthesized, and functionalizable trigonal planar quercetin-boronate esters was characterized by 1H, 13C, and 11B NMR spectra, FT-IR spectra, UV–Vis spectra, LC-MS/MS spectrometry, elemental analysis, and melting point measurement. Following the successful synthesis studies, quercetin-boronate esters have been tested over glucosidase enzyme inhibition, antimicrobial studies, computational insights, and in vitro anti-cancer activity against pancreatic cancer cells, respectively. QB1 significantly decreased cell viability at a 50 µM concentration compared to other boron compounds. The enzyme inhibition studies on quercetin-boronate esters demonstrated that α-glucosidase enzyme inhibitions were higher than the reference compound. IC50 values of QB1-QB4 against α-glucosidase were 5.92, 5.54, 5.68, and 6.79 μM, repsectivey. As expected, quercetin-boronate esters exhibited respectable activity against the biofilms of some bacteria. The MIC values of QB1-QB4 were 32.5 μg/mL against Enterococcus faecalis. In addition, the binding parameter values and binding sites were determined as a result of docking studies of quercetin-boronate esters. As a result of the scientific findings, quercetin-boronate ester compounds will certainly become important building blocks used in the future from organic synthesis to materials science and medicine.