Synthesis and antimicrobial activity of small cationic amphipathic aminobenzamide marine natural product mimics and evaluation of relevance against clinical isolates including ESBL-CARBA producing multi-resistant bacteria
A library of small aminobenzamide derivatives was synthesised to explore a cationic amphipathic motif found in marine natural antimicrobials. The most potent compound E23 displayed minimal inhibitory concentrations (MICs) of 0.5-2 mu g/ml against several Gram-positive bacterial strains, including me...
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| Published in | Bioorganic & medicinal chemistry Vol. 24; no. 22; pp. 5884 - 5894 |
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| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier
15.11.2016
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| Abstract | A library of small aminobenzamide derivatives was synthesised to explore a cationic amphipathic motif found in marine natural antimicrobials. The most potent compound E23 displayed minimal inhibitory concentrations (MICs) of 0.5-2 mu g/ml against several Gram-positive bacterial strains, including methicillin resistant Staphylococcus epidermidis (MRSE). E23 was also potent against 275 clinical isolates including Staphylococcus aureus, Enterococcus spp., Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumoniae, as well as methicillin-resistant S. aureus (MRSA), vancomycin-resistant enterococci (VRE), and ESBL-CARBA producing multi-resistant Gram-negative bacteria. The study demonstrates how structural motifs found in marine natural antimicrobials can be a valuable source for making novel antimicrobial lead-compounds. (C) 2016 Elsevier Ltd. All rights reserved. |
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| AbstractList | A library of small aminobenzamide derivatives was synthesised to explore a cationic amphipathic motif found in marine natural antimicrobials. The most potent compound E23 displayed minimal inhibitory concentrations (MICs) of 0.5-2 mu g/ml against several Gram-positive bacterial strains, including methicillin resistant Staphylococcus epidermidis (MRSE). E23 was also potent against 275 clinical isolates including Staphylococcus aureus, Enterococcus spp., Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumoniae, as well as methicillin-resistant S. aureus (MRSA), vancomycin-resistant enterococci (VRE), and ESBL-CARBA producing multi-resistant Gram-negative bacteria. The study demonstrates how structural motifs found in marine natural antimicrobials can be a valuable source for making novel antimicrobial lead-compounds. (C) 2016 Elsevier Ltd. All rights reserved. A library of small aminobenzamide derivatives was synthesised to explore a cationic amphipathic motif found in marine natural antimicrobials. The most potent compound E23 displayed minimal inhibitory concentrations (MICs) of 0.5-2μg/ml against several Gram-positive bacterial strains, including methicillin resistant Staphylococcus epidermidis (MRSE).E23 was also potent against 275 clinical isolates including Staphylococcus aureus, Enterococcus spp., Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumoniae, as well as methicillin-resistant S. aureus (MRSA), vancomycin-resistant enterococci (VRE), and ESBL-CARBA producing multi-resistant Gram-negative bacteria. The study demonstrates how structural motifs found in marine natural antimicrobials can be a valuable source for making novel antimicrobial lead-compounds. |
| Author | Haug, Tor Strom, Morten B. Lauksund, Silje Mishchenko, Ekaterina Blencke, Hans-Matti Sollid, Johanna U. Ericson Igumnova, Elizaveta M. Fredheim, Elizabeth G. Aarag Stensvag, Klara |
| Author_xml | – sequence: 1 givenname: Elizaveta M. surname: Igumnova fullname: Igumnova, Elizaveta M. organization: UiT, Fac Hlth Sci, Dept Pharm, NO-9037 Tromso, Norway – sequence: 2 givenname: Ekaterina surname: Mishchenko fullname: Mishchenko, Ekaterina organization: UiT, Fac Biosci Fisheries & Econ, Norwegian Coll Fishery Sci, NO-9037 Tromso, Norway – sequence: 3 givenname: Tor orcidid: 0000-0003-1104-5813 surname: Haug fullname: Haug, Tor organization: UiT, Fac Biosci Fisheries & Econ, Norwegian Coll Fishery Sci, NO-9037 Tromso, Norway – sequence: 4 givenname: Hans-Matti surname: Blencke fullname: Blencke, Hans-Matti organization: UiT, Fac Biosci Fisheries & Econ, Norwegian Coll Fishery Sci, NO-9037 Tromso, Norway – sequence: 5 givenname: Johanna U. Ericson surname: Sollid fullname: Sollid, Johanna U. Ericson organization: UiT, Fac Hlth Sci, Dept Med Biol, NO-9037 Tromso, Norway – sequence: 6 givenname: Elizabeth G. Aarag orcidid: 0000-0002-5004-5093 surname: Fredheim fullname: Fredheim, Elizabeth G. Aarag organization: UiT, Fac Hlth Sci, Dept Pharm, NO-9037 Tromso, Norway – sequence: 7 givenname: Silje surname: Lauksund fullname: Lauksund, Silje organization: UiT, Fac Hlth Sci, Dept Pharm, NO-9037 Tromso, Norway – sequence: 8 givenname: Klara orcidid: 0000-0002-4717-6711 surname: Stensvag fullname: Stensvag, Klara organization: UiT, Fac Biosci Fisheries & Econ, Norwegian Coll Fishery Sci, NO-9037 Tromso, Norway – sequence: 9 givenname: Morten B. orcidid: 0000-0003-1973-0778 surname: Strom fullname: Strom, Morten B. organization: UiT, Fac Hlth Sci, Dept Pharm, NO-9037 Tromso, Norway |
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| Keywords | Antimicrobial Multi-resistant bacteria ANTIBACTERIAL PEPTIDES ESBL-CARBA SUSCEPTIBILITY Antibacterial Aminobenzamides Marine natural product mimics BETA(2,2)-AMINO ACID STAPHYLOCOCCUS SPONGE Peptidomimetics PHARMACOPHORE ALKALOIDS ESBL–CARBA |
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| SubjectTerms | Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antimicrobial Cationic Peptides - chemical synthesis Antimicrobial Cationic Peptides - chemistry Antimicrobial Cationic Peptides - pharmacology Benzamides - chemical synthesis Benzamides - chemistry Benzamides - pharmacology Biochemistry & Molecular Biology Biological Products - chemical synthesis Biological Products - chemistry Biological Products - pharmacology Chemistry Chemistry, Medicinal Chemistry, Organic Dose-Response Relationship, Drug Drug Resistance, Multiple, Bacterial - drug effects Gram-Negative Bacteria - drug effects Gram-Positive Bacteria - drug effects Life Sciences & Biomedicine Microbial Sensitivity Tests Molecular Structure Pharmacology & Pharmacy Physical Sciences Science & Technology Structure-Activity Relationship |
| Title | Synthesis and antimicrobial activity of small cationic amphipathic aminobenzamide marine natural product mimics and evaluation of relevance against clinical isolates including ESBL-CARBA producing multi-resistant bacteria |
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