Quaternary salts derived from 3-substituted quinuclidine as potential antioxidative and antimicrobial agents

Two series of novel ammonium salts containing the quinuclidine moiety were prepared in order to evaluate their antioxidative, antibacterial and antifungal potential. The synthesized homologues of 3-hydroxy (QOH) and 3-chloroquinuclidine (QCl) with the different N-benzyl substituents at the -position...

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Bibliographic Details
Published in:Open Chemistry 2017-01, Vol.15 (1), p.320-331
Main Authors: Odžak, Renata, Šprung, Matilda, Soldo, Barbara, Skočibušić, Mirjana, Gudelj, Martina, Muić, Anita, Primožič, Ines
Format: Article
Language:English
Subjects:
antioxidative and antimicrobial activity
DNA damage protection activity
ORAC assay
quaternary ammonium salts
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Summary:Two series of novel ammonium salts containing the quinuclidine moiety were prepared in order to evaluate their antioxidative, antibacterial and antifungal potential. The synthesized homologues of 3-hydroxy (QOH) and 3-chloroquinuclidine (QCl) with the different N-benzyl substituents at the -position (bromo, chloro or nitro group) were obtained in very good yields and characterized by IR and NMR spectroscopies and elemental analysis. All compounds were tested for antioxidative activity using the oxygen radical absorbance capacity (ORAC) assay and among tested samples, N-p-nitrobenzyl-3-hydroxyquinuclidinium bromide (QOH-4) exhibited the highest antioxidative potential (293.80 nmol (TE) mL ), which was further investigated by the DNA nicking assay. The biological activity of selected compounds was evaluated by measuring the zone of inhibition and by determining the minimal inhibitory concentration (MIC) against three Gram-positive bacteria ( and ), three Gram-negative bacteria ( and ) and three fungi species ( and ). The bioactivity assay showed that some newly synthetized quaternary quinuclidinium compounds display a comparable or even better antibacterial and antifungal activity than the reference drugs such as gentamicin (GEN), cefotaxime (CTX) and amphotericin B (AMPHB). Among the tested compounds, N-p-chlorobenzyl-3-hydroxyquinuclidinium bromide (QOH-3) exhibited a considerable antibacterial efficiency against (MIC=0.39 µg mL ) and QOH-4 displayed a potent antifungal activity against (MIC=1.56 µg mL ).
ISSN:2391-5420
2391-5420
DOI:10.1515/chem-2017-0031