Surface modifications based on the cyanobacterial siderophore anachelin: from structure to functional biomaterials design |
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Authors: | Karl Gademann Joanna Kobylinska Jean-Yves Wach Tom M Woods |
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Institution: | (1) Chemical Synthesis Laboratory (SB-ISIC-LSYNC), Swiss Federal Institute of Technology (EPFL), 1015 Lausanne, Switzerland |
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Abstract: | This review describes the design, synthesis and evaluation of novel catechol based anchors for surface modification. The anachelin
chromophore, the catecholate fragment of the siderophore anachelin from the cyanobacterium Anabaena cylindrica, allows for the immobilization of polyethylene glycol (PEG) on titania and glass surfaces thus rendering them protein resistant
and antifouling. It is proposed that catecholate siderophores constitute a class of natural products useful for surface modification
similar to dihydroxyphenylalanine and dopamine derived compounds found in mussel adhesive proteins. Second-generation dopamine
derivatives featuring a quaternary ammonium group were found to be equally efficient in generating antifouling surfaces. The
anachelin chromophore, merged via a PEG linker to the glycopeptide antibiotic vancomycin, allowed for the generation of antimicrobial
surfaces through an operationally simple dip-and-rinse procedure. This approach offers an option for the prevention of nosocomial
infections through antimicrobial implants, catheters and stents. Consequences for the mild generation of functional biomaterials
are discussed and novel strategies for the immobilization of complex natural products, proteins and DNA on surfaces are presented. |
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Keywords: | Natural products Siderophores Surface chemistry Biomaterials Organic synthesis |
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