Covalent modification of γ-cyclodextrin with geraniol: An antibacterial agent with good thermal stability, solubility and biocompatibility

Colloids Surf B Biointerfaces. 2024 May:237:113841. doi: 10.1016/j.colsurfb.2024.113841. Epub 2024 Mar 12.

Abstract

Geraniol (Ger) is an essential oil molecule with excellent biological activity. High hydrophobicity and volatility limit its practical application. Cyclodextrins (CDs) are water-soluble cyclic oligosaccharides with hydrophobic cavities. Physical encapsulation of CDs to improve the solubility and stability of essential oil molecules is not satisfactory. Therefore, this study synthesized the γ-CD derivative (γ-CD-Ger) by grafting Ger onto γ-CD using a bromide-mediated method. Compared to the inclusion complexes (γ-CD/Ger) formed by both, the derivatives exhibit better solubility and thermal stability. The derivative has better antibacterial activity when the ratio of γ-CD to Ger was 1:2. In addition, the derivatives did not exhibit cytotoxic and hemolytic properties. These results indicate that this research provides a water-soluble antibacterial agent with a wide range of promising applications and offers new ideas for the application of alcohol hydrophobic molecules in aqueous systems.

Keywords: Antibacterial activity; Geraniol; Nucleophilic substitution; Thermostability; γ-cyclodextrin.

MeSH terms

  • Acyclic Monoterpenes*
  • Anti-Bacterial Agents / pharmacology
  • Cyclodextrins* / chemistry
  • Cyclodextrins* / pharmacology
  • Oils, Volatile*
  • Solubility
  • Water / chemistry
  • gamma-Cyclodextrins* / chemistry
  • gamma-Cyclodextrins* / pharmacology

Substances

  • gamma-Cyclodextrins
  • geraniol
  • Anti-Bacterial Agents
  • Cyclodextrins
  • Water
  • Oils, Volatile
  • Acyclic Monoterpenes