Literature DB >> 32296251

More QACs, more questions: Recent advances in structure activity relationships and hurdles in understanding resistance mechanisms.

Kelly R Morrison1, Ryan A Allen1, Kevin P C Minbiole2, William M Wuest1,3.   

Abstract

Quaternary ammonium compounds (QACs) are a class of antimicrobials that have been around for over a century; nevertheless, they have found continued renewal in the structures to which they can be appended. Ranging from antimicrobial polymers to adding novel modes of action to existing antibiotics, QACs have found ongoing use due to their potent properties. However, resistance against QACs has begun to emerge, and the mechanism of resistance is still only partially understood. In this review, we aim to summarize the current state of the field and what is known about the mechanisms of resistance so that the QACs of the future can be designed to be evermore efficacious and utilized to unearth the remaining mysteries that surround bacteria's resistance to them.

Entities:  

Keywords:  Antibiotic resistance; Disinfectants; Efflux Pumps; MultiQACs; Quaternary ammonium compounds

Year:  2019        PMID: 32296251      PMCID: PMC7158862          DOI: 10.1016/j.tetlet.2019.07.026

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  45 in total

1.  Scaffold-Hopping of Multicationic Amphiphiles Yields Three New Classes of Antimicrobials.

Authors:  Myles A Mitchell; Anthony A Iannetta; Megan C Jennings; Madison H Fletcher; William M Wuest; Kevin P C Minbiole
Journal:  Chembiochem       Date:  2015-09-11       Impact factor: 3.164

Review 2.  Cationic antiseptics: diversity of action under a common epithet.

Authors:  P Gilbert; L E Moore
Journal:  J Appl Microbiol       Date:  2005       Impact factor: 3.772

3.  Multistep Inhibition of α-Synuclein Aggregation and Toxicity in Vitro and in Vivo by Trodusquemine.

Authors:  Michele Perni; Patrick Flagmeier; Ryan Limbocker; Roberta Cascella; Francesco A Aprile; Céline Galvagnion; Gabriella T Heller; Georg Meisl; Serene W Chen; Janet R Kumita; Pavan K Challa; Julius B Kirkegaard; Samuel I A Cohen; Benedetta Mannini; Denise Barbut; Ellen A A Nollen; Cristina Cecchi; Nunilo Cremades; Tuomas P J Knowles; Fabrizio Chiti; Michael Zasloff; Michele Vendruscolo; Christopher M Dobson
Journal:  ACS Chem Biol       Date:  2018-06-28       Impact factor: 5.100

4.  Building a Better Quaternary Ammonium Compound (QAC): Branched Tetracationic Antiseptic Amphiphiles.

Authors:  Megan E Forman; Megan C Jennings; William M Wuest; Kevin P C Minbiole
Journal:  ChemMedChem       Date:  2016-06-01       Impact factor: 3.466

5.  Claramines: A New Class Of Broad-Spectrum Antimicrobial Agents With Bimodal Activity.

Authors:  Marine Blanchet; Diane Borselli; Anne Rodallec; Franck Peiretti; Nicolas Vidal; Jean-Michel Bolla; Carole Digiorgio; Kelly R Morrison; William M Wuest; Jean Michel Brunel
Journal:  ChemMedChem       Date:  2018-04-10       Impact factor: 3.466

6.  Total synthesis of [Ψ[C(═S)NH]Tpg4]vancomycin aglycon, [Ψ[C(═NH)NH]Tpg4]vancomycin aglycon, and related key compounds: reengineering vancomycin for dual D-Ala-D-Ala and D-Ala-D-Lac binding.

Authors:  Jian Xie; Akinori Okano; Joshua G Pierce; Robert C James; Simon Stamm; Christine M Crane; Dale L Boger
Journal:  J Am Chem Soc       Date:  2012-01-06       Impact factor: 15.419

7.  The major facilitator superfamily transporter MdtM contributes to the intrinsic resistance of Escherichia coli to quaternary ammonium compounds.

Authors:  Scarlett R Holdsworth; Christopher J Law
Journal:  J Antimicrob Chemother       Date:  2012-12-05       Impact factor: 5.790

8.  THE BACTERICIDAL PROPERTIES OF THE QUATERNARY SALTS OF HEXAMETHYLENETETRAMINE : III. THE RELATION BETWEEN CONSTITUTION AND BACTERICIDAL ACTION IN THE QUATERNARY SALTS OBTAINED FROM HALOGENACETYL COMPOUNDS.

Authors:  W A Jacobs; M Heidelberger; C G Bull
Journal:  J Exp Med       Date:  1916-05-01       Impact factor: 14.307

9.  Coordinated response of phospholipids and acyl components of membrane lipids in Pseudomonas putida A (ATCC 12633) under stress caused by cationic surfactants.

Authors:  Romina Marisa Heredia; Paola Sabrina Boeris; María Alicia Biasutti; Gastón Alberto López; Natalia Soledad Paulucci; Gloria Inés Lucchesi
Journal:  Microbiology       Date:  2014-10-03       Impact factor: 2.777

10.  Thiabicyclononane-Based Antimicrobial Polycations.

Authors:  Zhishuai Geng; M G Finn
Journal:  J Am Chem Soc       Date:  2017-10-20       Impact factor: 15.419

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  13 in total

Review 1.  Biological activity of quaternary ammonium salts and resistance of microorganisms to these compounds.

Authors:  Ewa Obłąk; Bożena Futoma-Kołoch; Anna Wieczyńska
Journal:  World J Microbiol Biotechnol       Date:  2021-01-11       Impact factor: 3.312

2.  Rigidity-Activity Relationships of bisQPC Scaffolds against Pathogenic Bacteria.

Authors:  Aaron C Spahr; Marina E Michaud; Lauren E Amoo; Christian A Sanchez; Cody E Hogue; Laura M Thierer; Michael R Gau; William M Wuest; Kevin P C Minbiole
Journal:  ChemMedChem       Date:  2022-05-24       Impact factor: 3.540

3.  Trivalent sulfonium compounds (TSCs): Tetrahydrothiophene-based amphiphiles exhibit similar antimicrobial activity to analogous ammonium-based amphiphiles.

Authors:  Javier A Feliciano; Austin J Leitgeb; Cassandra L Schrank; Ryan A Allen; Kevin P C Minbiole; William M Wuest; Robert G Carden
Journal:  Bioorg Med Chem Lett       Date:  2021-01-28       Impact factor: 2.823

4.  An Efficient Synthesis of 3-Alkylpyridine Alkaloids Enables Their Biological Evaluation.

Authors:  Anna R Kaplan; Cassandra L Schrank; William M Wuest
Journal:  ChemMedChem       Date:  2021-04-14       Impact factor: 3.540

5.  Combining Microscopy Assays of Bacteria-Surface Interactions To Better Evaluate Antimicrobial Polymer Coatings.

Authors:  M K L N Sikosana; A Ruland; C Werner; L D Renner
Journal:  Appl Environ Microbiol       Date:  2022-02-02       Impact factor: 5.005

6.  Design Guidelines for Cationic Pillar[n]arenes that Prevent Biofilm Formation by Gram-Positive Pathogens.

Authors:  Dana Kaizerman-Kane; Maya Hadar; Roymon Joseph; Dana Logviniuk; Yossi Zafrani; Micha Fridman; Yoram Cohen
Journal:  ACS Infect Dis       Date:  2021-03-03       Impact factor: 5.084

7.  Metallocene QACs: The Incorporation of Ferrocene Moieties into monoQAC and bisQAC Structures.

Authors:  Kyle J Sommers; Brian S Bentley; Robert G Carden; Savannah J Post; Ryan A Allen; Renee C Kontos; Jacob W Black; William M Wuest; Kevin P C Minbiole
Journal:  ChemMedChem       Date:  2020-11-26       Impact factor: 3.466

Review 8.  Back to Basics: Choosing the Appropriate Surface Disinfectant.

Authors:  Angelica Artasensi; Sarah Mazzotta; Laura Fumagalli
Journal:  Antibiotics (Basel)       Date:  2021-05-21

9.  Are Quaternary Ammonium Compounds, the Workhorse Disinfectants, Effective against Severe Acute Respiratory Syndrome-Coronavirus-2?

Authors:  Cassandra L Schrank; Kevin P C Minbiole; William M Wuest
Journal:  ACS Infect Dis       Date:  2020-05-15       Impact factor: 5.084

10.  Tricepyridinium-inspired QACs yield potent antimicrobials and provide insight into QAC resistance.

Authors:  Michelle A Garrison; Andrew R Mahoney; William M Wuest
Journal:  ChemMedChem       Date:  2020-10-16       Impact factor: 3.466

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