Structure-Activity Relationships in Alkoxylated Resorcinarenes: Synthesis, Structural Features, and Bacterial...

Area of Science:

• Supramolecular Chemistry
• Microbiology
• Organic Synthesis

Background:

• Resorcinarenes are macrocyclic compounds with diverse applications.
• Alkoxylation introduces functional groups that can alter molecular properties.
• Understanding structure-activity relationships is crucial for developing new materials and therapeutics.

Purpose of the Study:

• To synthesize novel alkoxylated resorcinarenes using mild catalytic conditions.
• To characterize the synthesized compounds and investigate their supramolecular properties.
• To evaluate the biological activity of these derivatives against clinically relevant bacterial strains, focusing on biofilm formation.

Main Methods:

• Synthesis of alkoxylated resorcinarenes via secondary and tertiary alcohols with iminodiacetic acid catalyst.
• Structural characterization using single-crystal X-ray diffraction and mass spectrometry.
• Biological evaluation of bacterial growth (OD600) and biofilm biomass (crystal violet assay) for four bacterial strains.

Main Results:

• Successful synthesis and characterization of novel alkoxylated resorcinarenes with branched alkyl chains.
• Mass spectrometry indicated potential for oligomeric species formation with supramolecular characteristics.
• Compound 2c (2-pentanol derivative) promoted biofilm formation in Staphylococcus aureus and Bacillus subtilis with low cytotoxicity.
• Compound 2e showed minimal impact on biofilm development.

Conclusions:

• Alkoxylated resorcinarenes possess dual utility as supramolecular building blocks and modulators of microbial behavior.
• Specific structural features of alkoxy chains influence microbial responses, potentially through membrane stress or quorum sensing interference.
• This study opens avenues for designing functional resorcinarene derivatives for both materials science and antimicrobial strategies.