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dc.contributor.authorSahariah, Priyanka
dc.contributor.authorGaware, Vivek S
dc.contributor.authorLieder, Ramona
dc.contributor.authorJónsdóttir, Sigríður
dc.contributor.authorHjálmarsdóttir, Martha Á
dc.contributor.authorSigurjonsson, Olafur E
dc.contributor.authorMásson, Már
dc.date.accessioned2014-09-30T15:05:24Zen
dc.date.available2014-09-30T15:05:24Zen
dc.date.issued2014-08en
dc.date.submitted2014en
dc.identifier.citationMar Drugs 2014, 12 (8):4635-58en
dc.identifier.issn1660-3397en
dc.identifier.pmid25196937en
dc.identifier.doi10.3390/md12084635en
dc.identifier.urihttp://hdl.handle.net/2336/331965en
dc.descriptionTo access publisher's full text version of this article, please click on the hyperlink in Additional Links field or click on the hyperlink at the top of the page marked Files. This article is open access.en
dc.description.abstractA series of water-soluble cationic chitosan derivatives were prepared by chemoselective functionalization at the amino group of five different parent chitosans having varying degrees of acetylation and molecular weight. The quaternary moieties were introduced at different alkyl spacer lengths from the polymer backbone (C-0, C-2 and C-6) with the aid of 3,6-di-O-tert-butyldimethylsilyl protection of the chitosan backbone, thus allowing full (100%) substitution of the free amino groups. All of the derivatives were characterized using 1H-NMR, 1H-1H COSY and FT-IR spectroscopy, while molecular weight was determined by GPC. Antibacterial activity was investigated against Gram positive S. aureus and Gram negative E. coli. The relationship between structure and activity/toxicity was defined, considering the effect of the cationic group's structure and its distance from the polymer backbone, as well as the degree of acetylation within a molecular weight range of 7-23 kDa for the final compounds. The N,N,N-trimethyl chitosan with 100% quaternization showed the highest antibacterial activity with moderate cytotoxicity, while increasing the spacer length reduced the activity. Trimethylammoniumyl quaternary ammonium moieties contributed more to activity than 1-pyridiniumyl moieties. In general, no trend in the antibacterial activity of the compounds with increasing molecular weight or degree of acetylation up to 34% was observed.
dc.description.sponsorshipIcelandic Research Fund/20443023) Nordforsk Public Private Partnership, Genis ehf,en
dc.language.isoenen
dc.publisherMDPIen
dc.relation.urlhttp://dx.doi.org/10.3390/md12084635en
dc.relation.urlhttp://www.ncbi.nlm.nih.gov/pmc/articles/PMC4145335/?report=readeren
dc.rightsopenAccessen
dc.subjectSóttvarniren
dc.subject.meshChitosan/chemical synthesisen
dc.subject.meshChitosan/chemistry*en
dc.subject.meshChitosan/pharmacology*en
dc.subject.meshAnti-Bacterial Agents/chemical synthesis*en
dc.subject.meshAnti-Bacterial Agents/chemistryen
dc.subject.meshAnti-Bacterial Agents/pharmacology*en
dc.subject.meshStructure-Activity Relationshipen
dc.subject.meshAcetylationen
dc.subject.meshCations/chemistry*en
dc.subject.meshCations/pharmacology*en
dc.subject.meshEscherichia coli/drug effectsen
dc.subject.meshMolecular Weighten
dc.subject.meshPolymers/chemistryen
dc.subject.meshPolymers/pharmacologyen
dc.subject.meshStaphylococcus aureus/drug effectsen
dc.subject.meshStructure-Activity Relationshipen
dc.titleThe effect of substituent, degree of acetylation and positioning of the cationic charge on the antibacterial activity of quaternary chitosan derivatives.en
dc.typeArticleen
dc.contributor.department1Faculty of Pharmaceutical Sciences, School of Health Sciences, University of Iceland, Hofsvallagata 53, IS-107 Reykjavík, Iceland. prs1@hi.is. 2Faculty of Pharmaceutical Sciences, School of Health Sciences, University of Iceland, Hofsvallagata 53, IS-107 Reykjavík, Iceland. vsg3@hi.is. 3The REModeL Lab, The Blood Bank, Landspitali University Hospital, Snorrabraut 60, 105 Reykjavik, Iceland. ramona@landspitali.is. 4Department of Chemistry, Science Institute, University of Iceland, Dunhagi 3, IS-107 Reykjavik, Iceland. sigga@hi.is. 5Department of _Biomedical Science, Faculty of_ Medicine, University of _Iceland, Stapi, Hringbraut 31, 101 Reykjavík, Iceland. hjalmars@hi.is. 6The REModeL Lab, The Blood Bank, Landspitali University Hospital, Snorrabraut 60, 105 Reykjavik, Iceland. oes@landspitali.is. 7Faculty of Pharmaceutical Sciences, School of Health Sciences, University of Iceland, Hofsvallagata 53, IS-107 Reykjavík,en
dc.identifier.journalMarine drugsen
dc.rights.accessOpen Accessen
refterms.dateFOA2018-09-12T13:47:02Z
html.description.abstractA series of water-soluble cationic chitosan derivatives were prepared by chemoselective functionalization at the amino group of five different parent chitosans having varying degrees of acetylation and molecular weight. The quaternary moieties were introduced at different alkyl spacer lengths from the polymer backbone (C-0, C-2 and C-6) with the aid of 3,6-di-O-tert-butyldimethylsilyl protection of the chitosan backbone, thus allowing full (100%) substitution of the free amino groups. All of the derivatives were characterized using 1H-NMR, 1H-1H COSY and FT-IR spectroscopy, while molecular weight was determined by GPC. Antibacterial activity was investigated against Gram positive S. aureus and Gram negative E. coli. The relationship between structure and activity/toxicity was defined, considering the effect of the cationic group's structure and its distance from the polymer backbone, as well as the degree of acetylation within a molecular weight range of 7-23 kDa for the final compounds. The N,N,N-trimethyl chitosan with 100% quaternization showed the highest antibacterial activity with moderate cytotoxicity, while increasing the spacer length reduced the activity. Trimethylammoniumyl quaternary ammonium moieties contributed more to activity than 1-pyridiniumyl moieties. In general, no trend in the antibacterial activity of the compounds with increasing molecular weight or degree of acetylation up to 34% was observed.


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