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dc.contributor.authorBakka, Thomas Aleksander
dc.contributor.authorStrøm, Morten B.
dc.contributor.authorAndersen, Jeanette Hammer
dc.contributor.authorGautun, Odd Reidar
dc.date.accessioned2017-09-07T07:54:49Z
dc.date.available2017-09-07T07:54:49Z
dc.date.issued2017-07-29
dc.description.abstractA library of 29 small 1,4-substituted 1,2,3-triazoles was prepared for studies of antimicrobial activity. The pharmacophore model investigated with these substrates was based on small peptidomimetics of antimicrobial peptides and antimicrobials isolated from marine organisms from sub-arctic regions. Using methyl 1,2,3-triazole-carboxylates and 1,2,3-triazole methyl ketones prepared through “click” chemistry we were able to synthesize the different cationic amphiphiles through three steps or less. Several structural modifications to the lipopohilic side and hydrophilic sides of the amphiphiles were investigated and compared with regards to antimicrobial activity and cytotoxicity in particular. The most promising amphiphile 10f displayed minimum inhibitory concentrations (MICs) between 4 - 16 µg/mL against Gram-positive Enterococcus faecalis, Staphylococcus aureus, Streptococcus agalacticae, and Gram-negative Escherichia coli and Pseudomonas aeruginosa. The decent level of antimicrobial activity and biofilm inhibition, short synthesis, and accessible reagents, makes this type of amphiphilic mimics interesting leads for further development.en_US
dc.descriptionAccepted manuscript version. Published version available at <a href=https://doi.org/10.1016/j.bmc.2017.07.060> https://doi.org/10.1016/j.bmc.2017.07.060 </a>en_US
dc.identifier.citationBakka TA, Strøm MB, Andersen JH, Gautun, OR. Methyl propiolate and 3-butynone: Starting points for synthesis of amphiphilic 1,2,3-triazole peptidomimetics for antimicrobial evaluation, Bioorganic & Medicinal Chemistry, 2017, ISSN 0968-0896, http://dx.doi.org/10.1016/j.bmc.2017.07.060.en_US
dc.identifier.cristinIDFRIDAID 1484519
dc.identifier.doihttps://doi.org/10.1016/j.bmc.2017.07.060
dc.identifier.issn0968-0896
dc.identifier.issn1464-3391
dc.identifier.urihttps://hdl.handle.net/10037/11419
dc.language.isoengen_US
dc.publisherElsevieren_US
dc.relation.journalBioorganic & Medicinal Chemistry
dc.relation.projectIDeu-repo/grantAgreement/RCN/ BIOTEK2021/224790/Norway/Biology-DrivenSynthesisfromMarineNaturalProductstoCommercialLeadCompounds//en_US
dc.rights.accessRightsopenAccessen_US
dc.subjectVDP::Matematikk og Naturvitenskap: 400::Kjemi: 440::Organisk kjemi: 441en_US
dc.subjectVDP::Mathematics and natural science: 400::Chemistry: 440::Organic chemistry: 441en_US
dc.titleMethyl propiolate and 3-butynone: starting points for synthesis of amphiphilic 1,2,3-triazole peptidomimetics for antimicrobial evaluationen_US
dc.typeJournal articleen_US
dc.typeTidsskriftartikkelen_US
dc.typePeer revieweden_US


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