Design, Synthesis, and Antifungal Activity of 3-substituted-2(5H)-Oxaboroles

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dc.contributor.authorCampbell, Roseen
dc.contributor.authorBuchbinder, Nicklas W. en
dc.contributor.authorSzwetkowski, Connoren
dc.contributor.authorZhu, Yumengen
dc.contributor.authorPiedl, Karlaen
dc.contributor.authorTruong, Mindyen
dc.contributor.authorMatson, John B.en
dc.contributor.authorSantos, Webster L.en
dc.contributor.authorMevers, Emilyen
dc.date.accessioned2024-12-19T17:50:29Zen
dc.date.available2024-12-19T17:50:29Zen
dc.date.issued2024-02-22en
dc.description.abstractNext generation antimicrobial therapeutics are desperately needed as new pathogens with multiple resistance mechanisms continually emerge. Two oxaboroles, tavaborole and crisaborole, were recently approved as topical treatments for onychomycosis and atopic dermatitis, respectively, warranting further studies into this privileged structural class. Herein, we report the antimicrobial properties of 3-substituted-2(5H)-oxaboroles, an unstudied family of medicinally relevant oxaboroles. Our results revealed minimum inhibitory concentrations as low as 6.25 and 5.20 μg/mL against fungal (e.g., Penicillium chrysogenum) and yeast (Saccharomyces cerevisiae) pathogens, respectively. These oxaboroles were nonhemolytic and nontoxic to rat myoblast cells (H9c2). Structure-activity relationship studies suggest that planarity is important for antimicrobial activity, possibly due to the effects of extended conjugation between the oxaborole and benzene rings.en
dc.description.versionPublished versionen
dc.format.extentPages 349-354en
dc.format.extent6 page(s)en
dc.format.mimetypeapplication/pdfen
dc.identifier.doihttps://doi.org/10.1021/acsmedchemlett.3c00463en
dc.identifier.eissn1948-5875en
dc.identifier.issn1948-5875en
dc.identifier.issue3en
dc.identifier.orcidMevers, Emily [0000-0001-7986-5610]en
dc.identifier.orcidMatson, John [0000-0001-7984-5396]en
dc.identifier.orcidSantos, Webster [0000-0002-4731-8548]en
dc.identifier.otherPMC10945556en
dc.identifier.pmid38505851en
dc.identifier.urihttps://hdl.handle.net/10919/123842en
dc.identifier.volume15en
dc.language.isoenen
dc.publisherAmerican Chemical Societyen
dc.relation.urihttps://www.ncbi.nlm.nih.gov/pubmed/38505851en
dc.rightsCreative Commons Attribution 4.0 Internationalen
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/en
dc.subjectOxaborolesen
dc.subjecttavaboroleen
dc.subjectMICen
dc.subjectantifungalen
dc.subjectantibacterialen
dc.titleDesign, Synthesis, and Antifungal Activity of 3-substituted-2(5H)-Oxaborolesen
dc.title.serialACS Medicinal Chemistry Lettersen
dc.typeArticle - Refereeden
dc.type.dcmitypeTexten
dc.type.otherArticleen
dcterms.dateAccepted2024-02-14en
pubs.organisational-groupVirginia Techen
pubs.organisational-groupVirginia Tech/Scienceen
pubs.organisational-groupVirginia Tech/Science/Chemistryen
pubs.organisational-groupVirginia Tech/Faculty of Health Sciencesen
pubs.organisational-groupVirginia Tech/All T&R Facultyen
pubs.organisational-groupVirginia Tech/Science/COS T&R Facultyen
pubs.organisational-groupVirginia Tech/Report testen

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