Interaction of lignin-derived dimer and eugenol-functionalized silica nanoparticles with supported lipid bilayers

Mahsa Moradipour, Emily K. Chase, M. Arif Khan, Shardrack O. Asare, Bert C. Lynn, Stephen E. Rankin, Barbara L. Knutson

Research output: Contribution to journalArticlepeer-review

19 Scopus citations


The potential to impart surfaces with specific lignin-like properties (i.e. resistance to microbes) remains relatively unexplored due to the lack of well-defined lignin-derived small molecules and corresponding surface functionalization strategies. Here, allyl-modified guaiacyl β-O-4 eugenol (G-eug) lignin-derived dimer is synthesized and attached to mesoporous silica nanoparticles (MSNPs) via click chemistry. The ability of G-eug lignin-dimer functionalized particles to interact with and disrupt synthetic lipid bilayers is compared to that of eugenol, a known natural antimicrobial. Spherical MSNPs (∼150 nm diameter with 4.5 nm pores) were synthesized using surfactant templating. Post-synthesis thiol (SH) attachment was performed using (3-mercaptopropyl) trimethoxysilane and quantified by Ellman's test. The resultant SH-MSNPs were conjugated with the G-eug dimers or eugenol by a thiol-ene reaction under ultraviolet light in the presence of a photo initiator. From thermogravimetric analysis (TGA), attachment densities of approximately 0.22 mmol eugenol/g particle and 0.13 mmol G-eug dimer/g particle were achieved. The interaction of the functionalized MSNPs with a phospholipid bilayers of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (representing model cell membranes) supported on gold surface was measured using Quartz Crystal Microbalance with Dissipation monitoring (QCM-D). Eugenol-grafted MSNPs in PBS (up to 1 mg/mL) associated with the bilayer and increased the mass adsorbed on the QCM-D sensor. In contrast, MSNPs functionalized with G-eug dimer show qualitatively different behavior, with more uptake and evidence of bilayer disruption at and above a particle concentration of 0.5 mg/mL. These results suggest that bio-inspired materials with conjugated lignin-derived small molecules can serve as a platform for novel antimicrobial coatings and therapeutic carriers.

Original languageEnglish
Article number111028
JournalColloids and Surfaces B: Biointerfaces
StatePublished - Jul 2020

Bibliographical note

Publisher Copyright:
© 2020


  • Eugenol
  • Lignin
  • Model cell membranes
  • Quartz crystal microbalance
  • Silica nanoparticle
  • Supported lipid bilayer

ASJC Scopus subject areas

  • Biotechnology
  • Surfaces and Interfaces
  • Physical and Theoretical Chemistry
  • Colloid and Surface Chemistry


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