Inspiration from Old Dyes: Tris(stilbene) Compounds as Potent Gram‐Positive Antibacterial Agents |
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| Authors: | Dr Ramiz A Boulos Nikki Y T Man Dr Nigel A Lengkeek Prof Katherine A Hammer Dr Niki F Foster Natalie A Stemberger Prof Brian W Skelton Pan Yu Wong Prof Boris Martinac Prof Thomas V Riley Prof Allan J McKinley Prof Scott G Stewart |
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| Institution: | 1. School of Chemistry and Biochemistry, The University of Western Australia, Crawley, WA 6009 (Australia), Fax: (+61)?8‐6488‐1005;2. Present Addresses: School of Chemical and Physical Sciences, Flinders University, Bedford Park, SA 5042 (Australia);3. School of Pathology and Laboratory Medicine, The University of Western Australia, Crawley, WA 6009 (Australia);4. Path West Laboratory Medicine (WA), Queen Elizabeth II Medical Centre, Nedlands, WA, 6009 (Australia);5. Centre for Microscopy, Characterisation and Analysis, University of Western Australia, Crawley 6009 WA (Australia);6. Victor Chang Cardiac Research Institute, Lowy Packer Building, Darlinghurst, NSW, 2010 (Australia);7. St Vincent's Clinical School, The University of New South Wales, Sydney, NSW 2052 (Australia) |
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| Abstract: | 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. |
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| Keywords: | antibacterial biological activity Heck cross‐coupling MRSA stilbenes |
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