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dc.contributor.authorWang, Chongqing
dc.contributor.authorLambert, Christopher
dc.contributor.authorHauser, Maurice
dc.contributor.authorDeuschmann, Adrian
dc.contributor.authorZeilinger, Carsten
dc.contributor.authorRottner, Klemens
dc.contributor.authorStradal, Theresia E B
dc.contributor.authorStadler, Marc
dc.contributor.authorSkellam, Elizabeth J
dc.contributor.authorCox, Russell J
dc.date.accessioned2020-10-28T14:15:11Z
dc.date.available2020-10-28T14:15:11Z
dc.date.issued2020-06-02
dc.identifier.citationChemistry. 2020 Jun 2. doi: 10.1002/chem.202002241.en_US
dc.identifier.pmid32484589
dc.identifier.doi10.1002/chem.202002241
dc.identifier.urihttp://hdl.handle.net/10033/622546
dc.description.abstractMutasynthesis of pyrichalasin H from Magnaporthe grisea NI980 yielded a series of unprecedented 4'-substituted cytochalasin analogues in titres as high as the wild-type system (≈60 mg L-1 ). Halogenated, O-alkyl, O-allyl and O-propargyl examples were formed, as well as a 4'-azido analogue. 4'-O-Propargyl and 4'-azido analogues reacted smoothly in Huisgen cycloaddition reactions, whereas p-Br and p-I compounds reacted in Pd-catalysed cross-coupling reactions. A series of examples of biotin-linked, dye-linked and dimeric cytochalasins was rapidly created. In vitro and in vivo bioassays of these compounds showed that the 4'-halogenated and azido derivatives retained their cytotoxicity and antifungal activities; but a unique 4'-amino analogue was inactive. Attachment of larger substituents attenuated the bioactivities. In vivo actin-binding studies with adherent mammalian cells showed that actin remains the likely intracellular target. Dye-linked compounds revealed visualisation of intracellular actin structures even in the absence of phalloidin, thus constituting a potential new class of actin-visualisation tools with filament-barbed end-binding specificity.en_US
dc.language.isoenen_US
dc.publisherWiley-VCHen_US
dc.rightsAttribution-NonCommercial-ShareAlike 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/4.0/*
dc.subjectcytochalasinsen_US
dc.subjectmolecular toolsen_US
dc.subjectmutasynthesisen_US
dc.subjectsemi-synthesisen_US
dc.titleDiversely Functionalised Cytochalasins through Mutasynthesis and Semi-Synthesis.en_US
dc.typeArticleen_US
dc.identifier.eissn1521-3765
dc.contributor.departmentHZI,Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7,38124 Braunschweig, Germany.en_US
dc.identifier.journalChemistry (Weinheim an der Bergstrasse, Germany)en_US
refterms.dateFOA2020-10-28T14:15:11Z
dc.source.journaltitleChemistry (Weinheim an der Bergstrasse, Germany)
dc.source.countryGermany


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