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New and potent quinuclidine based antimicrobial agents

Radman Kastelic, Andreja; Odžak, Renata; Pezdirc, Iskra; Sović, Karlo; Hrenar, Tomica; Čipak Gašparović, Ana; Skočibušić, Mirjana; Primožič, Ines (2019) New and potent quinuclidine based antimicrobial agents. Molecules, 24 (14). pp. 2675-2692. ISSN 1420-3049

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Developing new antibiotics is currently very important since antibiotic resistance is one of the biggest problems of global health today. In the search for a new class of potential antimicrobial agents, ten new compounds were designed and synthesized based on quinuclidinium heterocyclic core and oxime functional group. The antimicrobial activity was assessed against a panel of representative Gram-positive and Gram-negative bacteria. All compounds demonstrated potent activity against the tested microorganisms, with MIC values ranging from 0.25 to 256.00 μg/mL. Among the tested compounds, two quaternary compounds, para-N-chlorobenzyl and meta-N-bromobenzyl quinuclidinium oximes, displayed the most potent and broad-spectrum activity against both Gram-positive and Gram-negative bacterial strains (MIC values from 0.25 to 4.00 μg/mL), with the lowest value for the important multidrug resistant Gram-negative pathogen Pseudomonas aeruginosa. In the case of Klebsiella pneumoniae activity of those compounds are 256-fold and 16-fold better than gentamicin, respectively. MTT assay showed that compounds are nontoxic for human cell lines. Multi-way analysis was used to separately reduce dimensionality of quantum chemical data and biological activity data to obtain regression model and required parameters for the enhancement of biological activity.

Item Type: Article
Uncontrolled Keywords: Antimicrobial potency ; Quinuclidinium oximes ; Gram-positive and Gram- negative bacteria ; Multi-way analysis
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Molecular Medicine
Project titleProject leaderProject codeProject type
Aktivnošću i in silico usmjeren dizajn malih bioaktivnih molekula-ADESIRETomica HrenarIP-2016-06-3775HRZZ
Depositing User: Ana Čipak Gašparović
Date Deposited: 01 Aug 2019 07:32
DOI: 10.3390/molecules24142675

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