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dc.contributor.authorSoliga, Kevin J
dc.contributor.authorBär, Sofia I
dc.contributor.authorOberhuber, Natalie
dc.contributor.authorZeng, Haoxuan
dc.contributor.authorSchrey, Hedda
dc.contributor.authorSchobert, Rainer
dc.date.accessioned2021-12-03T15:36:38Z
dc.date.available2021-12-03T15:36:38Z
dc.date.issued2021-10-19
dc.identifier.citationMar Drugs. 2021 Oct 19;19(10):583. doi: 10.3390/md19100583.en_US
dc.identifier.pmid34677482
dc.identifier.doi10.3390/md19100583
dc.identifier.urihttp://hdl.handle.net/10033/623112
dc.description.abstractThe sponge metabolite ancorinoside B was prepared for the first time in 16 steps and 4% yield. It features a β-d-galactopyranosyl-(1→4)-β-d-glucuronic acid tethered to a d-aspartic acid-derived tetramic acid. Key steps were the synthesis of a fully protected d-lactose derived thioglycoside, its attachment to a C20-aldehyde spacer, functionalization of the latter with a terminal N-(β-ketoacyl)-d-aspartate, and a basic Dieckmann cyclization to close the pyrrolidin-2,4-dione ring with concomitant global deprotection. Ancorinoside B exhibited multiple biological effects of medicinal interest. It inhibited the secretion of the cancer metastasis-relevant matrix metalloproteinases MMP-2 and MMP-9, and also the growth of Staphylococcus aureus biofilms by ca 87% when applied at concentrations as low as 0.5 µg/mL. This concentration is far below its MIC of ca 67 µg/mL and thus unlikely to induce bacterial resistance. It also led to a 67% dispersion of preformed S. aureus biofilms when applied at a concentration of ca 2 µg/mL. Ancorinoside B might thus be an interesting candidate for the control of the general hospital, catheter, or joint protheses infections.en_US
dc.language.isoenen_US
dc.publisherMDPIen_US
dc.rightsAttribution 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjectMMP inhibitoren_US
dc.subjectancorinoside Ben_US
dc.subjectglycosyl tetramic aciden_US
dc.subjectmarine sponge metaboliteen_US
dc.subjectmicrobial biofilm inhibitoren_US
dc.titleSynthesis and Bioactivity of Ancorinoside B, a Marine Diglycosyl Tetramic Aciden_US
dc.typeArticleen_US
dc.identifier.eissn1660-3397
dc.contributor.departmentHZI,Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7,38124 Braunschweig, Germany.en_US
dc.identifier.journalMarine drugsen_US
dc.source.volume19
dc.source.issue10
refterms.dateFOA2021-12-03T15:36:39Z
dc.source.journaltitleMarine drugs
dc.source.countrySwitzerland


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Attribution 4.0 International
Except where otherwise noted, this item's license is described as Attribution 4.0 International