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Diversely Functionalised Cytochalasins through Mutasynthesis and Semi-Synthesis.
Wang, Chongqing; Lambert, Christopher; Hauser, Maurice; Deuschmann, Adrian; Zeilinger, Carsten; Rottner, Klemens; Stradal, Theresia E B; Stadler, Marc; Skellam, Elizabeth J; Cox, Russell J.
Afiliación
  • Wang C; Institute for Organic Chemistry and BMWZ, Leibniz University of Hannover, Schneiderberg 38, 30167, Hannover, Germany.
  • Lambert C; Department Microbial Drugs, Helmholtz Centre for Infection Research, Bldg. B, Room 175a, Inhoffenstrasse 7, 38124, Braunschweig, Germany.
  • Hauser M; Division of Molecular Cell Biology, Zoological Institute, Technische Universität Braunschweig, Spielmannstrasse 7, 38106, Braunschweig, Germany.
  • Deuschmann A; Institute for Organic Chemistry and BMWZ, Leibniz University of Hannover, Schneiderberg 38, 30167, Hannover, Germany.
  • Zeilinger C; Institute for Organic Chemistry and BMWZ, Leibniz University of Hannover, Schneiderberg 38, 30167, Hannover, Germany.
  • Rottner K; Institute for Organic Chemistry and BMWZ, Leibniz University of Hannover, Schneiderberg 38, 30167, Hannover, Germany.
  • Stradal TEB; Department of Cell Biology, Helmholtz Centre for Infection Research, Inhoffenstrasse 7, 38124, Braunschweig, Germany.
  • Stadler M; Division of Molecular Cell Biology, Zoological Institute, Technische Universität Braunschweig, Spielmannstrasse 7, 38106, Braunschweig, Germany.
  • Skellam EJ; Department of Cell Biology, Helmholtz Centre for Infection Research, Inhoffenstrasse 7, 38124, Braunschweig, Germany.
  • Cox RJ; Department Microbial Drugs, Helmholtz Centre for Infection Research, Bldg. B, Room 175a, Inhoffenstrasse 7, 38124, Braunschweig, Germany.
Chemistry ; 26(60): 13578-13583, 2020 Oct 27.
Article en En | MEDLINE | ID: mdl-32484589
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.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Citocalasinas Límite: Animals Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2020 Tipo del documento: Article País de afiliación: Alemania Pais de publicación: Alemania
Texto completo
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Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Citocalasinas Límite: Animals Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2020 Tipo del documento: Article País de afiliación: Alemania Pais de publicación: Alemania