Theoretical and experimental investigation of 1,4-dihydropyridine-based hexahydroquinoline-3-carboxylates: Photophysics and bovine serum albumin binding studies

Camargo da Luz L., Gözde Gündüz M. G., Beal R., Modernell Zanotto G., Ramires Kuhn E., Augusto Netz P., ...More

Journal of Photochemistry and Photobiology A: Chemistry, vol.429, 2022 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 429
  • Publication Date: 2022
  • Doi Number: 10.1016/j.jphotochem.2022.113915
  • Journal Name: Journal of Photochemistry and Photobiology A: Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Agricultural & Environmental Science Database, BIOSIS, Chemical Abstracts Core, Chimica, INSPEC
  • Keywords: 4-dihydropyridine, BSA, DFT calculation, Fluorescence quenching, Molecular docking, CRYSTAL-STRUCTURE, FLUORESCENCE, DERIVATIVES, BSA, NAPHTHALENE, COMPLEXES, SOLVENT, DOCKING
  • Hacettepe University Affiliated: Yes


© 2022 Elsevier B.V.In this article, the binding affinity of 1,4-dihydropyridine-based hexahydroquinoline-3-carboxylates with bovine serum albumin (BSA) was studied by electronic spectroscopies, quantum calculations, and molecular docking. These compounds were obtained by the one-pot microwave-assisted method via a modified Hantzsch reaction. The photophysical characterization showed in organic solutions absorption maxima in the UV region, ascribed to spin and symmetry allowed electronic transitions 1π–π*. In addition, they presented a main fluorescence emission in the violet-blue regions (406–445 nm), with a relatively large Stokes shift (54–81 nm), depending on the structure of the compounds. BSA fluorescence quenching experiments based on the intrinsic fluorescence of the Trp residues were successfully applied to these compounds, indicating strong interaction with BSA by a static mechanism. The docking simulations corroborated the strong interaction between the studied compounds and BSA, where the surroundings of Trp213 seemed to be the preferred interaction site for all compounds and were responsible for the fluorescence quenching effects.