Synthesis of water-soluble curcumin derivatives and their inhibition on lysozyme amyloid fibrillation

摘要

AbstractThe potential application of curcumin was heavily limited in biomedicine because of its poor solubility in pure water. To circumvent the detracting feature, two novel water-soluble amino acid modified curcumin derivatives (MLCandDLC) have been synthesized through the condensation reaction between curcumin and Nα-Fmoc-Nε-Boc-l-lysine. Benefiting from the enhanced solubility of 3.32×10?2g/mL forMLCand 4.66×10?2g/mL forDLC, the inhibition effects of the as-prepared derivatives on the amyloid fibrillation of lysozyme (HEWL) were investigated detaily in water solution. The obtained results showed that the amyloid fibrillation of HEWL was inhibited to a great extent when the concentrations ofMLCandDLCreach to 20.139mM and 49.622mM, respectively. The fluorescence quenching upon the addition of curcumin to HEWL provide a support for static and dynamic recombination quenching process. The binding driving force was assigned to classical hydrophobic interaction between curcumin derivatives and HEWL. In addition, UV–Vis absorption and circular dichroism (CD) spectra confirmed the change of the conformation of HEWL.Graphical Abstract展开▼