Effects of Synthetic Tetronamides and Methylated Denigrins on Bacterial Quorum Sensing and Biofilm Formation

Sweta Roy, Jaime A.M. Acosta, Milandip Karak, Isabela Ramirez-Velez, Kohei Torikai, Dacheng Ren, Luiz C.A. Barbosa

Research output: Contribution to journalArticlepeer-review

Abstract

Detrimental biofilms of bacterial pathogens cause chronic infections with a high-level tolerance to antibiotics. To identify new control agents, we synthesized and tested a total of 14 tetronamides (including 5 new compounds) and 6 denigrin intermediates on the model species Escherichia coli. At a concentration of 50 μg/mL, two tetronamides and two methylated denigrins exhibited significant inhibitory effects against biofilm formation of E. coli RP437, e.g., by 60 and 94%, respectively. Structural analysis of the tested compounds revealed that p-methoxybenzylidene and p-methoxyphenethyl moieties of denigrins are important for biofilm inhibition, while the former group is also essential to the activity against quorum sensing (QS) via AI-2. Specifically, tetramethyldenigrin B has strong inhibitory effects against both E. coli biofilm formation and AI-2-mediated QS and thus provides a promising lead structure for designing better control agents. Consistently, tetramethyldenigrin B also showed inhibitory activity against biofilm formation of uropathogenic E. coli. Together, these findings provide new insights for the rational design of novel biofilm and QS inhibitors.

Original languageEnglish (US)
Pages (from-to)37798-37807
Number of pages10
JournalACS Omega
Volume8
Issue number41
DOIs
StatePublished - Oct 17 2023

ASJC Scopus subject areas

  • General Chemistry
  • General Chemical Engineering

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