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dc.contributor.authorSoukup, Ondřej
dc.contributor.authorDoležal, Rafael
dc.contributor.authorMaliňák, David
dc.contributor.authorMarek, Jan
dc.contributor.authorSalajková, Šárka
dc.contributor.authorPasdiorová, Markéta
dc.contributor.authorHonegr, Jan
dc.contributor.authorKorábečný, Jan
dc.contributor.authorNachtigal, Petr
dc.contributor.authorNachon, Florian
dc.contributor.authorJun, Daniel
dc.contributor.authorKuča, Kamil
dc.date.accessioned2016-03-23T14:07:55Z
dc.date.available2016-03-23T14:07:55Z
dc.date.issued2016
dc.identifier.citationBioorganic & Medicinal Chemistry. 2016, vol. 24, issue 4, p. 841-848.cs
dc.identifier.issn0968-0896
dc.identifier.issn1464-3391
dc.identifier.urihttp://hdl.handle.net/10084/111398
dc.description.abstractIn the present paper, we describe the synthesis of a new group of 5-hydroxyisoquinolinium salts with different lengths of alkyl side-chain (C10–C18), and their chromatographic analysis and biological assay for in vitro activity against bacterial and fungal strains. We compare the lipophilicity and efficacy of hydroxylated isoquinolinium salts with the previously published (non-hydroxylated) isoquinolinium salts from the point of view of antibacterial and antifungal versatility and cytotoxic safety. Compound 11 (C18) had to be excluded from the testing due to its low solubility. Compounds 9 and 10 (C14, C16) showed only moderate efficacy against G+ bacteria, notably with excellent potency against Staphyloccocus aureus, but no effect against G− bacteria. In contrast, non-hydroxylated isoquinolinium salts showed excellent antimicrobial efficacy within the whole series, particularly 14 (C14) against G+ strains and 15 (C16) against fungi. The electronic properties and desolvation energies of 5-hydroxyisoquinolinium and isoquinolinium salts were studied by quantum-chemistry calculations employing B3LYP/6-311++G(d,p) method and an implicit water-solvent simulation model (SCRF). Despite the positive mesomeric effect of the hydroxyl moiety reducing the electron density of the quaternary nitrogen, it is probably the higher lipophilicity and lower desolvation energy of isoquinolinium salts, which is responsible for enhanced antimicrobial versatility and efficacy.cs
dc.language.isoencs
dc.publisherElseviercs
dc.relation.ispartofseriesBioorganic & Medicinal Chemistrycs
dc.relation.urihttp://dx.doi.org/10.1016/j.bmc.2016.01.006cs
dc.rightsCopyright © 2016 Elsevier Ltd. All rights reserved.cs
dc.subject5-Hydroxyisoquinolinium saltscs
dc.subjectSynthesiscs
dc.subjectAntimicrobial activitycs
dc.subjectLipophilicitycs
dc.subjectIsoquinolinium saltscs
dc.titleSynthesis, antimicrobial evaluation and molecular modeling of 5-hydroxyisoquinolinium salt series; the effect of the hydroxyl moietycs
dc.typearticlecs
dc.identifier.doi10.1016/j.bmc.2016.01.006
dc.type.statusPeer-reviewedcs
dc.description.sourceWeb of Sciencecs
dc.description.volume24cs
dc.description.issue4cs
dc.description.lastpage848cs
dc.description.firstpage841cs
dc.identifier.wos000368898500035


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