Chiral helix amplification and enhanced bioadhesion of two-component low molecular weight hydrogels regulated by OH to eradicate MRSA biofilms

Mater Horiz. 2025 Jan 20;12(2):575-586. doi: 10.1039/d4mh01213e.

Abstract

The supramolecular chemistry of small chiral molecules has attracted widespread attention owing to their similarity to natural assembly codes. Two-component low-molecular-weight (LMW) hydrogels are crucial as they form helical structures via chirality transfer, enabling diverse functions. Herein, we report a pair of two-component chiral LMW hydrogels based on the small molecular drugs baicalin (BA), scutellarin (SCU) and berberine (BBR). The two hydrogels exhibited different helicities and abilities to adhere to methicillin-resistant staphylococcus aureus (MRSA) biofilms. The BA or SCU can each laterally interact with BBR in a tail-to-tail configuration, forming a stable hydrophobic structure, while hydrophilic glucuronide groups are exposed to a water solution to form a hydrogel. However, the tiny variant steric hindrance of the terminal OH moiety of SCU affects π-π stacking in the layered assembly, resulting in SCU-BBR having much stronger chirality deviation and supramolecular chirality amplification than BA-BBR. Thereafter, the OH group in SCU-BBR forms more intermolecular hydrogen bonds with MRSA biofilms, enhancing stronger adhesion and better scavenging effects than BA-BBR. This work provides a unique chiral supramolecular assembly pattern, expands the antibacterial application prospect of a two-component LMW hydrogel accompanying chirality amplification, and provides a new perspective and strategy for biofilm removal.

MeSH terms

  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Apigenin / chemistry
  • Apigenin / pharmacology
  • Bacterial Adhesion / drug effects
  • Berberine / chemistry
  • Berberine / pharmacology
  • Biofilms* / drug effects
  • Flavonoids / chemistry
  • Flavonoids / pharmacology
  • Hydrogels* / chemistry
  • Hydrogels* / pharmacology
  • Methicillin-Resistant Staphylococcus aureus* / drug effects
  • Methicillin-Resistant Staphylococcus aureus* / physiology
  • Molecular Weight

Substances

  • Hydrogels
  • Anti-Bacterial Agents
  • Flavonoids
  • baicalin
  • Apigenin
  • Berberine