Catechol derivatives interact with bovine serum albumin: Correlation of non-covalent interactions and antioxidant activity

Int J Biol Macromol. 2023 Jul 31:244:125321. doi: 10.1016/j.ijbiomac.2023.125321. Epub 2023 Jun 10.

Abstract

The interactions of catechol derivatives with model transportation protein-bovine serum albumin (BSA) were deciphered by the multispectral techniques, molecular docking and multifunctional wavefunction (Multiwfn). The representative catechol derivatives caffeic acid (CA) and 1-monocaffeoyl glycerol (1-MCG) with an (E)-but-2-enoic acid and a 2,3-dihydroxypropyl(E)-but-2-enoate side chain, respectively, were chosen in present study. The interaction results revealed the extra non-polar interactions and abundant binding sites facilitate the easier and stronger binding of 1-MCG-BSA. The α-helix content of BSA decreased and the hydrophilicity around Tyr and Trp changed due to the different interaction between catechol and BSA. The H2O2-damaged RAW 264.7, HaCat and SH-SY5Y were applied to investigate the anti-ROS properties of the catechol-BSA complexes. The results illuminated that the 2,3-dihydroxypropyl(E)-but-2-enoate side chain of 1-MCG facilitated the preferable biocompatibility and antioxidant property of its binding complex. These results revealed that the interaction of catechol-BSA binding complexes could influence their biocompatibility and antioxidant properties.

Keywords: 1-monocaffeoyl glycerol; Antioxidant property; BSA; Catechol; Multi-spectroscopic analysis; Multifunctional wavefunction.

MeSH terms

  • Antioxidants* / chemistry
  • Binding Sites
  • Catechols / pharmacology
  • Humans
  • Hydrogen Peroxide
  • Molecular Docking Simulation
  • Neuroblastoma*
  • Protein Binding
  • Serum Albumin, Bovine / chemistry
  • Spectrometry, Fluorescence
  • Spectrophotometry, Ultraviolet
  • Thermodynamics

Substances

  • Antioxidants
  • Serum Albumin, Bovine
  • Hydrogen Peroxide
  • Catechols