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Pregled bibliografske jedinice broj: 1253326

Synthesis and Biological Evaluation of 3-Amidoquinuclidine Quaternary Ammonium Compounds as New Soft Antibacterial Agents


Odžak, Renata; Crnčević, Doris; Sabljić, Antonio; Primožič, Ines; Šprung, Matilda
Synthesis and Biological Evaluation of 3-Amidoquinuclidine Quaternary Ammonium Compounds as New Soft Antibacterial Agents // Pharmaceuticals, 16 (2023), 2; 187, 20 doi:10.3390/ph16020187 (međunarodna recenzija, članak, znanstveni)


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Naslov
Synthesis and Biological Evaluation of 3-Amidoquinuclidine Quaternary Ammonium Compounds as New Soft Antibacterial Agents

Autori
Odžak, Renata ; Crnčević, Doris ; Sabljić, Antonio ; Primožič, Ines ; Šprung, Matilda

Izvornik
Pharmaceuticals (1424-8247) 16 (2023), 2; 187, 20

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

Ključne riječi
soft antimicrobial agents ; quaternary ammonium salts ; quinuclidine scaffold

Sažetak
Quaternary ammonium compounds (QACs) are among the most effective antimicrobial agents that have been used for more than a century. However, due to the growing trend of bacterial resistance and high toxicity of QACs, research in this field remains a pressing matter. Recent studies of the structure– activity relationship suggest that the introduction of the amide functional group into QAC structures results in soft variants that retain their antimicrobial properties while opening the possibility of fine-tuned activity regulation. Here, we report the synthesis and structure-function study of three structurally distinct series of naturally derived soft QACs. The obtained 3-amidoquinuclidine QACs showed a broad range of antibacterial activities related to the hydrophobic-hydrophilic balance of the QAC structures. All three series yielded candidates with minimal inhibitory concentrations (MIC) in the single-digit μM range. Time-resolved growth analysis revealed subtle differences in the antibacterial activity of the selected candidates. The versatile MIC values were recorded in different nutrient media, suggesting that the media composition may have a dramatic impact on the antibacterial potential. The new QACs were found to have excellent potential to suppress bacterial biofilm formation while exhibiting low ability to induce bacterial resistance. In addition, the selected candidates were found to be less toxic than commercially available QACs and proved to be potential substrates for protease degradation. These data suggest that 3- amidoquinuclidine QACs could be considered as novel antimicrobial agents that pose a low threat to ecosystems and human health.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekti:
HRZZ-UIP-2020-02-2356 - Otkriće i razvoj novih biološki aktivnih kvaternih amonijevih spojeva derivata kinuklidina (QACBioAct) (Šprung, Matilda, HRZZ ) ( CroRIS)

Ustanove:
Prirodoslovno-matematički fakultet, Zagreb,
Prirodoslovno-matematički fakultet, Split

Poveznice na cjeloviti tekst rada:

doi www.mdpi.com

Citiraj ovu publikaciju:

Odžak, Renata; Crnčević, Doris; Sabljić, Antonio; Primožič, Ines; Šprung, Matilda
Synthesis and Biological Evaluation of 3-Amidoquinuclidine Quaternary Ammonium Compounds as New Soft Antibacterial Agents // Pharmaceuticals, 16 (2023), 2; 187, 20 doi:10.3390/ph16020187 (međunarodna recenzija, članak, znanstveni)
Odžak, R., Crnčević, D., Sabljić, A., Primožič, I. & Šprung, M. (2023) Synthesis and Biological Evaluation of 3-Amidoquinuclidine Quaternary Ammonium Compounds as New Soft Antibacterial Agents. Pharmaceuticals, 16 (2), 187, 20 doi:10.3390/ph16020187.
@article{article, author = {Od\v{z}ak, Renata and Crn\v{c}evi\'{c}, Doris and Sablji\'{c}, Antonio and Primo\v{z}i\v{c}, Ines and \v{S}prung, Matilda}, year = {2023}, pages = {20}, DOI = {10.3390/ph16020187}, chapter = {187}, keywords = {soft antimicrobial agents, quaternary ammonium salts, quinuclidine scaffold}, journal = {Pharmaceuticals}, doi = {10.3390/ph16020187}, volume = {16}, number = {2}, issn = {1424-8247}, title = {Synthesis and Biological Evaluation of 3-Amidoquinuclidine Quaternary Ammonium Compounds as New Soft Antibacterial Agents}, keyword = {soft antimicrobial agents, quaternary ammonium salts, quinuclidine scaffold}, chapternumber = {187} }
@article{article, author = {Od\v{z}ak, Renata and Crn\v{c}evi\'{c}, Doris and Sablji\'{c}, Antonio and Primo\v{z}i\v{c}, Ines and \v{S}prung, Matilda}, year = {2023}, pages = {20}, DOI = {10.3390/ph16020187}, chapter = {187}, keywords = {soft antimicrobial agents, quaternary ammonium salts, quinuclidine scaffold}, journal = {Pharmaceuticals}, doi = {10.3390/ph16020187}, volume = {16}, number = {2}, issn = {1424-8247}, title = {Synthesis and Biological Evaluation of 3-Amidoquinuclidine Quaternary Ammonium Compounds as New Soft Antibacterial Agents}, keyword = {soft antimicrobial agents, quaternary ammonium salts, quinuclidine scaffold}, chapternumber = {187} }

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


Citati:





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