Wang, C.; Lambert, C.; Hauser, M.; Deuschmann, A.; Zeilinger, C. et al.: Diversely Functionalised Cytochalasins through Mutasynthesis and Semi-Synthesis. In: Chemistry – A European Journal 26 (2020), Nr. 60, S. 13578-13583. DOI: https://doi.org/10.1002/chem.202002241
Abstract: | |
Mutasynthesis 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. | |
License of this version: | CC BY-NC 4.0 Unported |
Document Type: | Article |
Publishing status: | publishedVersion |
Issue Date: | 2020 |
Appears in Collections: | Naturwissenschaftliche Fakultät |
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