Expanding the Variety of Pyridinium‐Based bis‐QACs with Antimicrobial Properties: Investigation into Linker Structure‐Activity Correlation.

Expanding the Variety of Pyridinium‐Based bis‐QACs with Antimicrobial Properties: Investigation into Linker Structure‐Activity Correlation. Full article

Journal

ChemMedChem
ISSN: 1860-7179 , E-ISSN: 1860-7187

Output data

Year: 2025, Article number : e202400972, Pages count : DOI: 10.1002/cmdc.202400972

Authors

Vereshchagin Anatoly ¹ , Frolov Nikita A. ¹ , Tyutin Alexander A. ^1,2 , Tyurina Alexandra N. ² , Seferyan Mary A. ¹ , Detusheva Elena V. ^1,2 , Son Elizabeth ³ , Saverina Evgeniya A. ^1,4

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Organic Chemistry, Leninsky procp., 47, 119991 Moscow, RUSSIAN FEDERATION
2	Mendeleev University of Chemical Technology of Russia, Departments of the Faculty of Natural Sciences and Department of Chemistry and Technology of Biomedical Drugs, Miusskaya square 9, 125047 Moscow, Russia
3	Federal Budget Institution of Science «State research center for applied microbiology and biotechnology», 142279 Obolensk, Serpukhov, Moscow Region, Russia
4	Federal State Budgetary Educational Institution of Higher Education, Tula State University, Prospekt Lenina 92, 300012 Tula, Russia

For decades quaternary ammonium compounds (QACs) have served as main component of a top antiseptic and disinfectant compositions. Among them, bis-QACs are the most prominent and effective class of biocides. Although mono-QACs still dominate the antiseptic market, their activity against Gram-negative bacteria is largely inferior to bis-QACs. Moreover, the new wave of bacterial resistance during the COVID-19 pandemic is threatening the efficiency of popular antiseptics. Therefore, the requirement for novel biocides is urgent. Reported here is a unified and simple two-step synthesis to achieve novel biocide's architectures with aromatic linkers. Thus, a series of 14 bis-QACs have been prepared using an Ullman-type reaction following by N-alkylation. The most prominent compounds showed strong bioactivity against a panel of nineteen microbial pathogens, multi-resistant bacterial ESKAPEE strains, fungi and biofilms, including strains, which acquired resistance during COVID-19 in 2021. Moreover, significant improvements in antibiofilm action were observed, where bis-QACs 5 c and 6 a outperformed gold standard pyridinium antiseptic octenidine. These findings will serve as a good basis for further studies of bis-QACs architectures as highly effective biocides.

Vereshchagin A. , Frolov N.A. , Tyutin A.A. , Tyurina A.N. , Seferyan M.A. , Detusheva E.V. , Son E. , Saverina E.A.
Expanding the Variety of Pyridinium‐Based bis‐QACs with Antimicrobial Properties: Investigation into Linker Structure‐Activity Correlation.
ChemMedChem. 2025. e202400972 . DOI: 10.1002/cmdc.202400972 WOS OpenAlex

Web of science:	WOS:001419020000001
OpenAlex:	W4406437326

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