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

Javier A Feliciano; Austin J Leitgeb; Cassandra L Schrank; Ryan A Allen; Kevin P C Minbiole; William M Wuest; Robert G Carden

doi:10.1016/j.bmcl.2021.127809

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

Bioorg Med Chem Lett. 2021 Apr 1:37:127809. doi: 10.1016/j.bmcl.2021.127809. Epub 2021 Jan 28.

Authors

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

Affiliations

¹ Department of Chemistry, Villanova University, Villanova, PA 19085, United States.
² Department of Chemistry, Emory University, Atlanta, GA 30322, Unites States.
³ Department of Chemistry, Emory University, Atlanta, GA 30322, Unites States. Electronic address: william.wuest@emory.edu.
⁴ Department of Chemistry, Villanova University, Villanova, PA 19085, United States. Electronic address: rcarden@villanova.edu.

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.

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

Publication types

Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Bacteria / drug effects*
Dose-Response Relationship, Drug
Erythrocytes / drug effects
Erythrocytes / metabolism
Humans
Microbial Sensitivity Tests
Molecular Structure
Quaternary Ammonium Compounds / chemical synthesis
Quaternary Ammonium Compounds / chemistry
Quaternary Ammonium Compounds / pharmacology*
Structure-Activity Relationship
Sulfonium Compounds / chemical synthesis
Sulfonium Compounds / chemistry
Sulfonium Compounds / pharmacology*
Surface-Active Agents / chemical synthesis
Surface-Active Agents / chemistry
Surface-Active Agents / pharmacology*
Thiophenes / chemical synthesis
Thiophenes / chemistry
Thiophenes / pharmacology*

Substances

Quaternary Ammonium Compounds
Sulfonium Compounds
Surface-Active Agents
Thiophenes
tetrahydrothiophene

Abstract

Publication types

MeSH terms

Substances

Grants and funding