Synthesis, Antimicrobial Effect and Lipophilicity-Activity Dependence of Three Series of Dichained N-Alkylammonium Salts

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60162694%3AG44__%2F19%3A00537389" target="_blank" >RIV/60162694:G44__/19:00537389 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00179906:_____/19:10402699

Výsledek na webu

<a href="https://onlinelibrary.wiley.com/doi/10.1002/slct.201902357" target="_blank" >https://onlinelibrary.wiley.com/doi/10.1002/slct.201902357</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/slct.201902357" target="_blank" >10.1002/slct.201902357</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis, Antimicrobial Effect and Lipophilicity-Activity Dependence of Three Series of Dichained N-Alkylammonium Salts

Popis výsledku v původním jazyce

Quaternary ammonium salts belong to the group of cationic surfactants and their structure, especially the length of the alkyl chain, plays a significant role in its activity against various microorganisms. Globally, there is a growing need to develop novel compounds due to the increasing resistance of microorganisms to antimicrobial agents. Three series of quaternary ammonium compounds based on dichained N-alkylammonium salts were synthesized with different carbon chain lengths (C-8, C-10, C-12, C-14, C-16). These compounds were characterized with analytical methods and tested in vitro for antibacterial, antifungal, antiviral and antialgal activities. In addition, the determination of their critical micelle concentrations, lipophilicity and cytotoxicity were likewise performed to assess potential lipophilicity-activity dependence. Almost all compounds showed a high efficacy against bacterial and fungal strains. Significant effects against Varicella zoster virus and algae were also noticed. Some of novel drugs outperformed standard benzalkonium salts. The expected trend of the correlation of an increase of cytotoxicity with the length of carbon chain was confirmed. These compounds show a higher potential as disinfectants rather than antiseptics due to their cytotoxic potential and low selectivity for microbes over mammalian cells.

Název v anglickém jazyce

Synthesis, Antimicrobial Effect and Lipophilicity-Activity Dependence of Three Series of Dichained N-Alkylammonium Salts

Popis výsledku anglicky

Quaternary ammonium salts belong to the group of cationic surfactants and their structure, especially the length of the alkyl chain, plays a significant role in its activity against various microorganisms. Globally, there is a growing need to develop novel compounds due to the increasing resistance of microorganisms to antimicrobial agents. Three series of quaternary ammonium compounds based on dichained N-alkylammonium salts were synthesized with different carbon chain lengths (C-8, C-10, C-12, C-14, C-16). These compounds were characterized with analytical methods and tested in vitro for antibacterial, antifungal, antiviral and antialgal activities. In addition, the determination of their critical micelle concentrations, lipophilicity and cytotoxicity were likewise performed to assess potential lipophilicity-activity dependence. Almost all compounds showed a high efficacy against bacterial and fungal strains. Significant effects against Varicella zoster virus and algae were also noticed. Some of novel drugs outperformed standard benzalkonium salts. The expected trend of the correlation of an increase of cytotoxicity with the length of carbon chain was confirmed. These compounds show a higher potential as disinfectants rather than antiseptics due to their cytotoxic potential and low selectivity for microbes over mammalian cells.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10400 - Chemical sciences

Projekt

<a href="/cs/project/NV18-09-00181" target="_blank" >NV18-09-00181: Vývoj polyvalentního dekontaminačního činidla</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2019

Kód důvěrnosti údajů

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

Název periodika

ChemistrySelect

ISSN

2365-6549

e-ISSN

2365-6549

Svazek periodika

4

Číslo periodika v rámci svazku

41

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

9

Strana od-do

12076-12084

Kód UT WoS článku

000495129900016

EID výsledku v databázi Scopus

2-s2.0-85075008649