Literature DB >> 33516911

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

Javier A Feliciano1, Austin J Leitgeb1, Cassandra L Schrank2, Ryan A Allen2, Kevin P C Minbiole1, William M Wuest3, Robert G Carden4.   

Abstract

Recent advances in the development of quaternary ammonium compounds (QACs) have focused on new structural motifs to increase bioactivity, but significantly less studied has been the change from ammonium- to sulfonium-based disinfectants. Herein, we report the synthesis of structurally analogous series of quaternary ammonium and trivalent sulfonium compounds (TSCs). The bioactivity profiles of these compounds generally mirror each other, and the antibacterial activity of sulfonium-based THT-18 was found to be comparable to the commercial disinfectant, BAC. The development of these compounds presents a new avenue for further study of disinfectants to combat the growing threat of bacterial resistance.
Copyright © 2021 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Antiseptics; Benzalkonium chloride; Methicillin-resistant Staphylococcus aureus (MRSA); Quaternary ammonium compounds; Trivalent sulfonium compounds

Mesh:

Substances:

Year:  2021        PMID: 33516911      PMCID: PMC7965331          DOI: 10.1016/j.bmcl.2021.127809

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  26 in total

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Authors:  P B PRICE
Journal:  Arch Surg       Date:  1950-07

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Authors:  Jing Qin; Jiangna Guo; Qiming Xu; Zhiqiang Zheng; Hailei Mao; Feng Yan
Journal:  ACS Appl Mater Interfaces       Date:  2017-03-15       Impact factor: 9.229

Review 4.  Advancements in the Development of Non-Nitrogen-Based Amphiphilic Antiseptics to Overcome Pathogenic Bacterial Resistance.

Authors:  Robert G Carden; Kyle J Sommers; Cassandra L Schrank; Austin J Leitgeb; Javier A Feliciano; William M Wuest; Kevin P C Minbiole
Journal:  ChemMedChem       Date:  2020-10-13       Impact factor: 3.466

Review 5.  Recent development of membrane-active molecules as antibacterial agents.

Authors:  Nan Zhang; Shutao Ma
Journal:  Eur J Med Chem       Date:  2019-09-27       Impact factor: 6.514

6.  The antimicrobial activity, hydrophobicity and toxicity of tri(n-alkyl)sulfoniums and tris(n-alkylphenyl) sulfoniums, and their relationships.

Authors:  Michiasa Hirayama
Journal:  Biocontrol Sci       Date:  2011-12       Impact factor: 0.982

7.  The antimicrobial activity, toxicity and antimicrobial mechanism of a new type of tris(alkylphenyl)sulfonium.

Authors:  Michiasa Hirayama
Journal:  Biocontrol Sci       Date:  2012-03       Impact factor: 0.982

8.  An Investigation into Rigidity-Activity Relationships in BisQAC Amphiphilic Antiseptics.

Authors:  Renee C Kontos; Stephanie A Schallenhammer; Brian S Bentley; Kelly R Morrison; Javier A Feliciano; Julia A Tasca; Anna R Kaplan; Mark W Bezpalko; W Scott Kassel; William M Wuest; Kevin P C Minbiole
Journal:  ChemMedChem       Date:  2018-12-18       Impact factor: 3.466

9.  Quaternary Ammonium Compounds: An Antimicrobial Mainstay and Platform for Innovation to Address Bacterial Resistance.

Authors:  Megan C Jennings; Kevin P C Minbiole; William M Wuest
Journal:  ACS Infect Dis       Date:  2015-05-29       Impact factor: 5.084

Review 10.  The potential of antimicrobial peptides as biocides.

Authors:  Garry Laverty; Sean P Gorman; Brendan F Gilmore
Journal:  Int J Mol Sci       Date:  2011-10-06       Impact factor: 5.923

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  2 in total

1.  Quaternary Phosphonium Compounds: An Examination of Non-Nitrogenous Cationic Amphiphiles That Evade Disinfectant Resistance.

Authors:  Kyle J Sommers; Marina E Michaud; Cody E Hogue; Amber M Scharnow; Lauren E Amoo; Ashley A Petersen; Robert G Carden; Kevin P C Minbiole; William M Wuest
Journal:  ACS Infect Dis       Date:  2022-01-25       Impact factor: 5.084

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

  2 in total

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