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Synthetic mimics of antimicrobial peptides from triaryl scaffolds.

Abstract：

:In this report, we describe the synthesis of a new series of small amphiphilic aromatic compounds that mimic the essential properties of cationic antimicrobial peptides using Suzuki-Miyaura coupling. The new design allowed the easy tuning of the conformational restriction, controlled by introduction of intramolecular hydrogen bonds, and the overall hydrophobicity by modifications to the central ring and the side chains. This approach allowed us to better understand the influence of these features on the antimicrobial activity and selectivity. We found that the overall hydrophobicity had a more significant impact on antimicrobial and hemolytic activity than the conformational stiffness. A novel compound was discovered which has MICs of 0.78 μg/mL against S. Aureus and 6.25 μg/mL against E. Coli, similar to the well-known antimicrobial peptide, MSI-78.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Thaker HD,Sgolastra F,Clements D,Scott RW,Tew GN

doi

10.1021/jm101410t

subject

Has Abstract

pub_date

2011-04-14 00:00:00

pages

2241-54

issue

7

eissn

0022-2623

issn

1520-4804

journal_volume

54

pub_type

杂志文章

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