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A Fluorescent Teixobactin Analogue.

Michael A Morris1, Melody Malek1, Mohammad H Hashemian1

  • 1Department of Chemistry, University of California, Irvine, Irvine, California 92697, United States.

ACS Chemical Biology
|February 12, 2020
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a fluorescent teixobactin analogue, Lys(Rhod)9,Arg10-teixobactin, which retains antibiotic activity against Gram-positive bacteria. This labeled compound allows visualization of teixobactin

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Area of Science:

  • Medicinal Chemistry
  • Microbiology
  • Biochemistry

Background:

  • Teixobactin is a potent antibiotic effective against Gram-positive bacteria.
  • Understanding the mechanism of action and cellular targets of antibiotics is crucial for combating resistance.
  • Developing tools to visualize antibiotic-cell interactions aids in drug discovery and development.

Purpose of the Study:

  • To synthesize and characterize a fluorescently labeled teixobactin analogue.
  • To investigate the cellular localization and binding of the fluorescent teixobactin analogue in Gram-positive bacteria.
  • To assess the antibiotic activity and utility of the fluorescent analogue as a research probe.

Main Methods:

  • Solid-phase peptide synthesis was employed to create the fluorescent teixobactin analogue, Lys(Rhod)9,Arg10-teixobactin.
  • Regioselective labeling with a rhodamine fluorophore was performed during synthesis.
  • Minimum inhibitory concentrations (MICs) were determined for bacterial panels.
  • Fluorescence microscopy was used to visualize cellular localization in bacteria, including colocalization studies with vancomycin.

Main Results:

  • The fluorescent teixobactin analogue, Lys(Rhod)9,Arg10-teixobactin, was successfully synthesized and retained partial antibiotic activity (MICs 4-8 μg/mL).
  • Microscopy revealed septal and lateral staining in Gram-positive bacteria treated with the fluorescent analogue, indicating cell wall precursor targeting.
  • Colocalization with vancomycin confirmed binding to cell wall precursors, while controls showed minimal staining.

Conclusions:

  • Lys(Rhod)9,Arg10-teixobactin is a functional fluorescent probe for studying Gram-positive bacteria.
  • The probe provides insights into the mechanism of action of teixobactin by visualizing its interaction with cell wall synthesis.
  • This fluorescent analogue can be a valuable tool for future research on teixobactin and bacterial cell wall biology.