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Inspiration from Old Dyes: Tris(stilbene) Compounds as Potent Gram‐Positive Antibacterial Agents
Author(s) -
Boulos Ramiz A.,
Man Nikki Y. T.,
Lengkeek Nigel A.,
Hammer Katherine A.,
Foster Niki F.,
Stemberger Natalie A.,
Skelton Brian W.,
Wong Pan Yu,
Martinac Boris,
Riley Thomas V.,
McKinley Allan J.,
Stewart Scott G.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201303119
Subject(s) - staphylococcus aureus , antibacterial activity , moraxella catarrhalis , microbiology and biotechnology , clindamycin , chemistry , vancomycin , antibiotics , minimum inhibitory concentration , bacteria , biology , streptococcus pneumoniae , genetics
Herein we describe the preparation and structure‐activity relationship studies on range of stilbene based compounds and their antibacterial activity. Two related compounds, each bearing carboxylic acid moieties, exhibit good activity against several bacterial strains, including methicillin‐resistant Staphylococcus aureus MRSA (ATCC 33592 and NCTC 10442). Compound 10 was most active against Moraxella catarrhalis with minimum inhibitory concentrations (MICs) of 0.12–0.25 μg mL −1 and against Staphylococcus spp. with MICs ranging from 2–4 μg mL −1 . The derivative 17 showed increased activity with MICs of 0.06–0.25 μg mL −1 against M. catarrhalis and 0.12–1 against Staphylococcus spp . This level of activity is similar to that reported for S. aureus for antibiotics, such as vancomycin, with MICs of ≤2.0 μg mL −1 and clindamycin with MICs of ≤0.5 μg mL −1 . As an indicator of toxicity, 17 was tested for its ability to lyse sheep erythrocytes, and showed low haemolytic activity. Such results highlight the value of tris(stilbene) compounds as antibacterial agents providing suitable properties for further development.