Synthesis and characterization of heptakis(methylaminoethanol)-β-cyclodextrin, carvacrol complexation and evaluation of antioxidant, antibacterial and antibiofilm activities

Cyclodextrins are widely explored as drug delivery systems for pharmaceutical applications. Here, we synthesized and characterized a novel β-cyclodextrin derivative functionalized with seven methylaminoethanol groups (βCD-MEA). The functionalization effects on water solubility, self-assembly behavior, toxicity, antibacterial activity, and drug complexation were investigated. Dynamic light scattering and microscopy images revealed βCD-MEA forms water soluble quasi -spherical nanoaggregates. Toxicological evaluation on Artemia salina indicated no toxicity of βCD-MEA, while antibacterial biofilm assays demonstrated its ability to reduce preformed Staphylococcus aureus biofilm. The potential of βCD-MEA as a drug delivery system was assessed using carvacrol as a drug model. The inclusion complex of βCD-MEA and carvacrol was prepared via freeze-drying, and key parameters such as apparent stability constant, complexation efficiency, drug loading capacity, drug entrapment efficiency, and dry content were determined. The size and morphology of the βCD-MEA/Carvacrol nanoaggregates were also examined. The complexed carvacrol retained its radical scavenging activity, exhibited antibacterial effects against S. aureus and Escherichia coli , and reduced both the formation and the amount of preformed biofilm S. aureus . The intrinsic ability of the βCD-MEA nanoaggregates to affect the preformed biofilm of S. aureus , combined with its potential as a nanocarrier for drug delivery, suggest βCD-MEA as a promising novel candidate in nanobiotics.