Inhibition of Pseudomonas aeruginosa Biofilm Formation with Bromoageliferin Analogues
- Robert W. Huigens
- ,
- Justin J. Richards
- ,
- Gina Parise
- ,
- T. Eric Ballard
- ,
- Wei Zeng
- ,
- Rajendar Deora
- , and
- Christian Melander
Abstract
Two analogues of the marine natural product bromoageliferin have been synthesized and subsequently assayed for the ability to inhibit the formation of Pseudomonas aeruginosa biofilms. Both compounds inhibited the ability of Pseudomonas aeruginosa strains PAO1 and PA14 to form biofilms; however, they displayed differential toxicity to planktonic bacteria. The cis analogue, CAGE, was found to possess greater toxicity than the trans analogue, TAGE. These compounds have no structural homology to any known inhibitors of Pseudomonas aeruginosa biofilms.
†
North Carolina State University.
‡
Program in Molecular Genetics, Wake Forest University Health Sciences.
§
Department of Microbiology and Immunology, Wake Forest University Health Sciences.
*
In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.
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, 3462-3473. https://doi.org/10.1016/j.bmc.2011.04.026
- Chang Liu, Roberta J. Worthington, Christian Melander, Hui Wu. A New Small Molecule Specifically Inhibits the Cariogenic Bacterium Streptococcus mutans in Multispecies Biofilms. Antimicrobial Agents and Chemotherapy 2011, 55
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, 2679-2687. https://doi.org/10.1128/AAC.01496-10
- Steven A. Rogers, Erick A. Lindsey, Daniel C. Whitehead, Trey Mullikin, Christian Melander. Synthesis and biological evaluation of 2-aminoimidazole/carbamate hybrid anti-biofilm and anti-microbial agents. Bioorganic & Medicinal Chemistry Letters 2011, 21
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, 1257-1260. https://doi.org/10.1016/j.bmcl.2010.12.057
- Lindsay Kalan, Gerard D. Wright. Antibiotic adjuvants: multicomponent anti-infective strategies. Expert Reviews in Molecular Medicine 2011, 13 https://doi.org/10.1017/S1462399410001766
- Kelly C. Peach, Walter M. Bray, Nicholas J. Shikuma, Nadine C. Gassner, R. Scott Lokey, Fitnat H. Yildiz, Roger G. Linington. An image-based 384-well high-throughput screening method for the discovery of biofilm inhibitors in Vibrio cholerae. Molecular BioSystems 2011, 7
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- Ali Al-Mourabit, Manuel A. Zancanella, Supriya Tilvi, Daniel Romo. Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids. Natural Product Reports 2011, 28
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- Samuel Reyes, Robert W. Huigens III, Zhaoming Su, Michel L. Simon, Christian Melander. Synthesis and biological activity of 2-aminoimidazole triazoles accessed by Suzuki–Miyaura cross-coupling. Organic & Biomolecular Chemistry 2011, 9
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- Denis S. Ermolat'ev, Jitender B. Bariwal, Hans P. L. Steenackers, Sigrid C. J. De Keersmaecker, Erik V. Van der Eycken. Concise and Diversity‐Oriented Route toward Polysubstituted 2‐Aminoimidazole Alkaloids and Their Analogues. Angewandte Chemie International Edition 2010, 49
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- Denis S. Ermolat'ev, Jitender B. Bariwal, Hans P. L. Steenackers, Sigrid C. J. De Keersmaecker, Erik V. Van der Eycken. Concise and Diversity-Oriented Route toward Polysubstituted 2-Aminoimidazole Alkaloids and Their Analogues. Angewandte Chemie 2010, 122
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- Cynthia A. Bunders, Justin J. Richards, Christian Melander. Identification of aryl 2-aminoimidazoles as biofilm inhibitors in Gram-negative bacteria. Bioorganic & Medicinal Chemistry Letters 2010, 20
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, 3797-3800. https://doi.org/10.1016/j.bmcl.2010.04.042
- S. A. Rogers, R. W. Huigens, J. Cavanagh, C. Melander. Synergistic Effects between Conventional Antibiotics and 2-Aminoimidazole-Derived Antibiofilm Agents. Antimicrobial Agents and Chemotherapy 2010, 54
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- Dinty J. Musk. Zinc Fingered: New Compounds that Thwart Gram‐Positive Biofilm Formation by Sequestering Zinc. ChemBioChem 2010, 11
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- Katherine M. Schmalzer, Marc A. Benson, Dara W. Frank. Activation of ExoU Phospholipase Activity Requires Specific C-Terminal Regions. Journal of Bacteriology 2010, 192
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- Steven A. Rogers, Joseph D. Bero, Christian Melander. Chemical Synthesis and Biological Screening of 2‐Aminoimidazole‐Based Bacterial and Fungal Antibiofilm Agents. ChemBioChem 2010, 11
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- Robert W. Huigens, Samuel Reyes, Catherine S. Reed, Cynthia Bunders, Steven A. Rogers, Andrew T. Steinhauer, Christian Melander. The chemical synthesis and antibiotic activity of a diverse library of 2-aminobenzimidazole small molecules against MRSA and multidrug-resistant A. baumannii. Bioorganic & Medicinal Chemistry 2010, 18
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, 663-674. https://doi.org/10.1016/j.bmc.2009.12.003
- Zhaoming Su, Steven A. Rogers, W. Steve McCall, Alicia C. Smith, Sindhu Ravishankar, Trey Mullikin, Christian Melander. A nitroenolate approach to the synthesis of 4,5-disubstituted-2-aminoimidazoles. Pilot library assembly and screening for antibiotic and antibiofilm activity. Organic & Biomolecular Chemistry 2010, 8
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- Steven A. Rogers, Daniel C. Whitehead, Trey Mullikin, Christian Melander. Synthesis and bacterial biofilm inhibition studies of ethyl N-(2-phenethyl) carbamate derivatives. Organic & Biomolecular Chemistry 2010, 8
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- Barbara Forte, Beatrice Malgesini, Claudia Piutti, Francesca Quartieri, Alessandra Scolaro, Gianluca Papeo. A Submarine Journey: The Pyrrole-Imidazole Alkaloids. Marine Drugs 2009, 7
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, 705-753. https://doi.org/10.3390/md7040705
- Justin J. Richards, Christian Melander. Controlling Bacterial Biofilms. ChemBioChem 2009, 10
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- Jeffrey L. Veesenmeyer, Alan R. Hauser, Thiago Lisboa, Jordi Rello. Pseudomonas aeruginosa virulence and therapy: Evolving translational strategies*. Critical Care Medicine 2009, 37
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- Robert L. Giles, John D. Sullivan, Andrew M. Steiner, Ryan E. Looper. Addition–Hydroamination Reactions of Propargyl Cyanamides: Rapid Access to Highly Substituted 2‐Aminoimidazoles. Angewandte Chemie 2009, 121
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- Steven A. Rogers, Michael Krayer, Jonathan S. Lindsey, Christian Melander. Tandem dispersion and killing of bacteria from a biofilm. Org. Biomol. Chem. 2009, 7
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- Zhong Jin. Muscarine, imidazole, oxazole and thiazole alkaloids. Natural Product Reports 2009, 26
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