Catalytic degradation of N-acyl-homoserine lactone using a copper complex of a TACN derivative: implications for quorum sensing interference

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389013%3A_____%2F25%3A00640885" target="_blank" >RIV/61389013:_____/25:00640885 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00216208:11310/25:10510299

Výsledek na webu

<a href="https://pubs.rsc.org/en/content/articlelanding/2025/dt/d5dt01612f" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2025/dt/d5dt01612f</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/D5DT01612F" target="_blank" >10.1039/D5DT01612F</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Catalytic degradation of N-acyl-homoserine lactone using a copper complex of a TACN derivative: implications for quorum sensing interference

Popis výsledku v původním jazyce

Medical treatment of bacterial biofilms represents a significant challenge, not only in the case of implant-associated infections but also in chronic inflammation of soft tissues. Therefore, further research is crucial to develop strategies that prevent biofilm formation at early stages, where quorum sensing (QS) signalling molecules that facilitate bacterial communication play a key role. In this study, we investigated the catalytic properties of an N-substituted triazacyclononane-copper(II) complex (Cu(II)-iPr2TACN), which mimicked the enzymatic activity of an acylase in the hydrolysis reaction of N-acyl-homoserine lactone (AHL), disrupting the QS in the bacterial biofilm as a result. Specifically, we focused on kinetic experiments involving the degradation of newly developed model AHLs with an acyl group derived from azobenzene as a chromophore label, enabling UV-VIS detection. ESI-MS was employed to identify the degradation products. Our results demonstrated sufficient hydrolytic activity against the model signalling molecules within relatively short time intervals under body temperature, blood pH and inflammation site conditions, with disruption occurring via lactone ring cleavage followed by further hydrolysis of the acyl fragment of the amide. To our knowledge, this is the first use of such complexes to degrade quorum sensing molecules. In addition, a novel UV-VIS active azodye chromophore-containing model substrate of a quorum sensing molecule was established for quorum quenching degradation studies and critically compared to other natural and synthetic quorum sensing molecules.

Název v anglickém jazyce

Catalytic degradation of N-acyl-homoserine lactone using a copper complex of a TACN derivative: implications for quorum sensing interference

Popis výsledku anglicky

Medical treatment of bacterial biofilms represents a significant challenge, not only in the case of implant-associated infections but also in chronic inflammation of soft tissues. Therefore, further research is crucial to develop strategies that prevent biofilm formation at early stages, where quorum sensing (QS) signalling molecules that facilitate bacterial communication play a key role. In this study, we investigated the catalytic properties of an N-substituted triazacyclononane-copper(II) complex (Cu(II)-iPr2TACN), which mimicked the enzymatic activity of an acylase in the hydrolysis reaction of N-acyl-homoserine lactone (AHL), disrupting the QS in the bacterial biofilm as a result. Specifically, we focused on kinetic experiments involving the degradation of newly developed model AHLs with an acyl group derived from azobenzene as a chromophore label, enabling UV-VIS detection. ESI-MS was employed to identify the degradation products. Our results demonstrated sufficient hydrolytic activity against the model signalling molecules within relatively short time intervals under body temperature, blood pH and inflammation site conditions, with disruption occurring via lactone ring cleavage followed by further hydrolysis of the acyl fragment of the amide. To our knowledge, this is the first use of such complexes to degrade quorum sensing molecules. In addition, a novel UV-VIS active azodye chromophore-containing model substrate of a quorum sensing molecule was established for quorum quenching degradation studies and critically compared to other natural and synthetic quorum sensing molecules.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2025

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Dalton Transactions

ISSN

1477-9226

e-ISSN

1477-9234

Svazek periodika

54

Číslo periodika v rámci svazku

43

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

15

Strana od-do

16106-16120

Kód UT WoS článku

001592180000001

EID výsledku v databázi Scopus

2-s2.0-105020799935