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Pregled bibliografske jedinice broj: 973857

Discovery of novel quaternary ammonium compounds based on quinuclidine-3-ol as new potential antimicrobial candidates


Bazina, Linda; Maravić, Ana; Krce, Lucija; Soldo, Barbara; Odžak, Renata; Bučević Popović, Viljemka; Aviani, Ivica; Primožič, Ines; Šprung, Matilda
Discovery of novel quaternary ammonium compounds based on quinuclidine-3-ol as new potential antimicrobial candidates // European journal of medicinal chemistry, 163 (2019), -; 626-635 doi:10.1016/j.ejmech.2018.12.023 (međunarodna recenzija, članak, znanstveni)


Naslov
Discovery of novel quaternary ammonium compounds based on quinuclidine-3-ol as new potential antimicrobial candidates

Autori
Bazina, Linda ; Maravić, Ana ; Krce, Lucija ; Soldo, Barbara ; Odžak, Renata ; Bučević Popović, Viljemka ; Aviani, Ivica ; Primožič, Ines ; Šprung, Matilda

Izvornik
European journal of medicinal chemistry (0223-5234) 163 (2019); 626-635

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Quaternary ammonium compounds, antimicrobial activity, quinuclidine, cytotoxicity

Sažetak
Quaternary ammonium compounds (QACs) are amphiphilic molecules displaying a broad-spectrum of antibacterial activity. QACs are commonly used antiseptics in industrial, home and hospital settings. Given the emergence of the QAC-resistant bacteria, there is an urgent need to design new QACs with good antimicrobial activity, able to escape the host resistance mechanism. Therefore, a series of QACs derived from quinuclidine-3-ol and an alkyl chain of variable length (QOH-C3 to -C14), was designed and synthesized. The antimicrobial potential of the new monoquaternary QACs was surveyed against seventeen strains of emerging food spoilage and pathogenic microorganisms, including clinical multidrug-resistant ESKAPE isolates. The QOH-C14 proved to have the strongest antimicrobial activity. It was highly active against all pathogens tested, particularly against the Gram-positive bacteria with minimal inhibitory concentrations (MICs) ranging from 0.06 to 3.9 µg/mL, and fungi exerting the MIC90 between 0.12 and 3.9 µg/mL. The potency of QOH-C14, confirmed that alkyl chains are an important part of the structure with their lengths playing a critical role in bioactivity of these compounds. The atomic force microscopy images show the disruption of a cell membrane upon the treatment with QOH-C14. These results were additionally confirmed by flow cytometry and fluorescence microscopy. A relatively low toxicity toward healthy human cells underline that QOH-C14 has a potential as new QAC antimicrobial candidate.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


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