Literature DB >> 30288228

2-Aminobenzimidazoles as antibiofilm agents against Salmonella enterica serovar Typhimurium.

William M Huggins1, T Vu Nguyen1, Nicholas A Hahn1, James T Baker1, Laura G Kuo2, Darpan Kaur2, Roberta J Melander1, John S Gunn2, Christian Melander1.   

Abstract

Serovars within the species Salmonella enterica are some of the most common food and water-borne pathogens worldwide. Some S. enterica serovars have shown a remarkable ability to persist both inside and outside the human body. Salmonella enterica serovar Typhi can cause chronic, asymptomatic infection of the human gallbladder. This organism's ability to survive inside the gallbladder centers around its ability to form biofilms on gallstone surfaces. Currently, chronic carriage of S. Typhi is treated by invasive methods, which are not well suited to areas where Salmonella carriage is prevalent. Herein, we report 2-aminobenzimidazoles that inhibit S. enterica serovar Typhimurium (a surrogate for S. Typhi) biofilm formation in low micromolar concentrations. Modifications to the head, tail, and linker regions of the original hit compound elucidated new, more effective analogues that inhibit S. Typhimurium biofilm formation while being non-toxic to planktonic bacterial growth.

Entities:  

Year:  2018        PMID: 30288228      PMCID: PMC6151450          DOI: 10.1039/c8md00298c

Source DB:  PubMed          Journal:  Medchemcomm        ISSN: 2040-2503            Impact factor:   3.597


  19 in total

1.  Gallstones play a significant role in Salmonella spp. gallbladder colonization and carriage.

Authors:  Robert W Crawford; Roberto Rosales-Reyes; María de la Luz Ramírez-Aguilar; Oscar Chapa-Azuela; Celia Alpuche-Aranda; John S Gunn
Journal:  Proc Natl Acad Sci U S A       Date:  2010-02-22       Impact factor: 11.205

2.  A 2-aminobenzimidazole that inhibits and disperses gram-positive biofilms through a zinc-dependent mechanism.

Authors:  Steven A Rogers; Robert W Huigens; Christian Melander
Journal:  J Am Chem Soc       Date:  2009-07-29       Impact factor: 15.419

3.  Microwave-assisted one-pot synthesis and anti-biofilm activity of 2-amino-1H-imidazole/triazole conjugates.

Authors:  Hans Steenackers; Denis Ermolat'ev; Tran Thi Thu Trang; Bharat Savalia; Upendra K Sharma; Ami De Weerdt; Anamik Shah; Jozef Vanderleyden; Erik V Van der Eycken
Journal:  Org Biomol Chem       Date:  2014-04-24       Impact factor: 3.876

4.  Structure-activity relationship of 4(5)-aryl-2-amino-1H-imidazoles, N1-substituted 2-aminoimidazoles and imidazo[1,2-a]pyrimidinium salts as inhibitors of biofilm formation by Salmonella typhimurium and Pseudomonas aeruginosa.

Authors:  Hans P L Steenackers; Denis S Ermolat'ev; Bharat Savaliya; Ami De Weerdt; David De Coster; Anamik Shah; Erik V Van der Eycken; Dirk E De Vos; Jozef Vanderleyden; Sigrid C J De Keersmaecker
Journal:  J Med Chem       Date:  2010-12-20       Impact factor: 7.446

5.  The discovery of N-1 substituted 2-aminobenzimidazoles as zinc-dependent S. aureus biofilm inhibitors.

Authors:  Erick A Lindsey; Christopher M Brackett; Trey Mullikin; Cristina Alcaraz; Christian Melander
Journal:  Medchemcomm       Date:  2012-09-18       Impact factor: 3.597

6.  Enhancing the anti-biofilm activity of 5-aryl-2-aminoimidazoles through nature inspired dimerisation.

Authors:  Tran Thi Thu Trang; Lise Dieltjens; Geert Hooyberghs; Kai Waldrant; Denis S Ermolat'ev; Erik V Van der Eycken; Hans P L Steenackers
Journal:  Bioorg Med Chem       Date:  2018-01-31       Impact factor: 3.641

7.  Structure-activity relationship of 2-hydroxy-2-aryl-2,3-dihydro-imidazo[1,2-a]pyrimidinium salts and 2N-substituted 4(5)-aryl-2-amino-1H-imidazoles as inhibitors of biofilm formation by Salmonella Typhimurium and Pseudomonas aeruginosa.

Authors:  Hans P L Steenackers; Denis S Ermolat'ev; Bharat Savaliya; Ami De Weerdt; David De Coster; Anamik Shah; Erik V Van der Eycken; Dirk E De Vos; Jozef Vanderleyden; Sigrid C J De Keersmaecker
Journal:  Bioorg Med Chem       Date:  2011-04-19       Impact factor: 3.641

8.  Concise and diversity-oriented route toward polysubstituted 2-aminoimidazole alkaloids and their analogues.

Authors:  Denis S Ermolat'ev; Jitender B Bariwal; Hans P L Steenackers; Sigrid C J De Keersmaecker; Erik V Van der Eycken
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-03       Impact factor: 15.336

9.  Identification and characterization of 4-[4-(3-phenyl-2-propen-1-yl)-1-piperazinyl]-5H-pyrimido[5,4-b]indole derivatives as Salmonella biofilm inhibitors.

Authors:  Stijn Chris Arnold Robijns; Bart De Pauw; Bram Loosen; Arnaud Marchand; Patrick Chaltin; Sigrid C J De Keersmaecker; Jos Vanderleyden; Hans P L Steenackers
Journal:  FEMS Immunol Med Microbiol       Date:  2012-05-08

10.  Eradication of Salmonella Typhimurium infection in a murine model of typhoid fever with the combination of probiotic Lactobacillus fermentum ME-3 and ofloxacin.

Authors:  Kai Truusalu; Raik-Hiio Mikelsaar; Paul Naaber; Tõnis Karki; Tiiu Kullisaar; Mihkel Zilmer; Marika Mikelsaar
Journal:  BMC Microbiol       Date:  2008-08-04       Impact factor: 3.605

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  5 in total

1.  Natural products as inspiration for the development of bacterial antibiofilm agents.

Authors:  Roberta J Melander; Akash K Basak; Christian Melander
Journal:  Nat Prod Rep       Date:  2020-07-01       Impact factor: 13.423

2.  The Abundance and Organization of Salmonella Extracellular Polymeric Substances in Gallbladder-Mimicking Environments and In Vivo.

Authors:  Mark M Hahn; Juan F González; Regan Hitt; Lauren Tucker; John S Gunn
Journal:  Infect Immun       Date:  2021-08-16       Impact factor: 3.441

3.  Development of small molecules that work cooperatively with ciprofloxacin to clear salmonella biofilms in a chronic gallbladder carriage model.

Authors:  Katherine J Woolard; Jenna L Sandala; Roberta J Melander; John S Gunn; Christian Melander
Journal:  Eur J Med Chem       Date:  2022-02-19       Impact factor: 6.514

Review 4.  Recent Advances in Anti-virulence Therapeutic Strategies With a Focus on Dismantling Bacterial Membrane Microdomains, Toxin Neutralization, Quorum-Sensing Interference and Biofilm Inhibition.

Authors:  Osmel Fleitas Martínez; Marlon Henrique Cardoso; Suzana Meira Ribeiro; Octavio Luiz Franco
Journal:  Front Cell Infect Microbiol       Date:  2019-04-02       Impact factor: 5.293

Review 5.  Strategies and Approaches for Discovery of Small Molecule Disruptors of Biofilm Physiology.

Authors:  Michael A Trebino; Rahul D Shingare; John B MacMillan; Fitnat H Yildiz
Journal:  Molecules       Date:  2021-07-29       Impact factor: 4.411

  5 in total

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