Journal article
Positional isomers of biphenyl antimicrobial peptidomimetic amphiphiles
ACS Medicinal Chemistry Letters, Vol.12(3), pp.413-419
2021
Abstract
Small-molecule antimicrobial peptidomimetic amphiphiles represent a promising class of novel antimicrobials with the potential for widespread therapeutic application. To investigate the role of spatial positioning for key hydrophobic and hydrophilic groups on the antimicrobial efficacy and selectivity, positional isomers of the lead biphenyl antimicrobial peptidomimetic compound 1 were synthesized and subjected to microbial growth inhibition and mammalian toxicity assays. Positional isomer 4 exhibited 4–8× increased efficacy against the pathogenic Gram-negative bacteria Pseudomonas aeruginosa and Escherichia coli (MIC = 2 μg/mL), while isomers 2, 3, and 7 exhibited a 4× increase in activity against Acinetobacter baumannii (MIC = 4 μg/mL). Changes in molecular shape had a significant impact on Gram-negative antibacterial efficacy and the resultant spectrum of activity, whereas all structural isomers exhibited significant efficacy (MIC = 0.25–8 μg/mL) against Gram-positive bacterial pathogens (e.g., methicillin-resistant Staphylococcus aureus, Streptococcus pneumoniae, and Enterococcus faecalis).
Details
- Title
- Positional isomers of biphenyl antimicrobial peptidomimetic amphiphiles
- Authors/Creators
- A.J. Tague (Author/Creator)P. Putsathit (Author/Creator)T.V. Riley (Author/Creator)P.A. Keller (Author/Creator)S.G. Pyne (Author/Creator)
- Publication Details
- ACS Medicinal Chemistry Letters, Vol.12(3), pp.413-419
- Publisher
- American Chemical Society
- Identifiers
- 991005544741907891
- Copyright
- © 2021 American Chemical Society
- Murdoch Affiliation
- School of Medical, Molecular and Forensic Sciences
- Language
- English
- Resource Type
- Journal article
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- Collaboration types
- Domestic collaboration
- Citation topics
- 2 Chemistry
- 2.190 Surfactants, Lipid Bilayers & Antimicrobial Peptides
- 2.190.857 Antimicrobial Peptides
- Web Of Science research areas
- Chemistry, Medicinal
- ESI research areas
- Chemistry