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New synthetic polymers called antibacterial oligothioetheramides (AOTs) show potent antimicrobial activity. These AOTs offer tunable backbone hydrophobicity, leading to effective bacterial membrane permeabilization with low toxicity.

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Area of Science:

  • Biochemistry
  • Materials Science
  • Medicinal Chemistry

Background:

  • Antimicrobial peptides (AMPs) are promising antibiotic alternatives but have limitations like poor toxicology and proteolysis.
  • Synthetic AMP mimics often focus on side-chain charge and hydrophobicity, neglecting backbone effects.
  • Developing protease-resistant synthetic antimicrobials with tunable properties is crucial.

Purpose of the Study:

  • To synthesize and evaluate a new class of antibacterial oligothioetheramides (AOTs) with precisely controlled backbone hydrophobicity.
  • To investigate the relationship between AOT backbone hydrophobicity, conformation, and antimicrobial activity.
  • To assess the safety and efficacy of AOTs against clinically relevant pathogens.

Main Methods:

  • Developed a rapid assembly method for sequence-defined oligothioetheramides (oligoTEAs).
  • Synthesized AOTs with systematic variations in backbone hydrophobicity.
  • Evaluated AOTs for membrane permeabilization, antibacterial activity (MIC), and toxicity against red blood cells (RBCs) and HEK293 cells.

Main Results:

  • AOTs lyse bacterial cells through membrane permeabilization.
  • Backbone hydrophobicity and macromolecular conformation are key determinants of AOT activity.
  • Certain AOTs exhibited potent activity (MIC ~ 0.5-5 μM) against pathogens in serum with minimal toxicity.

Conclusions:

  • Precise control over AOT backbone hydrophobicity enables the design of potent and selective antimicrobial agents.
  • AOTs represent a promising class of synthetic antimicrobials with improved properties over traditional AMPs.
  • Identified key design parameters for next-generation antibacterial oligothioetheramides.