Synthesis, characterization and photo-bactericidal activity of silanized xanthene-modified bacterial cellulose membranes
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We report on the functionalization of wet bacterial cellulose sheets towards photo-bactericidal materials that produce singlet oxygen (1O2) upon illumination. Pre-modification was carried out by a silane chemistry approach in order to make the cellulosic material accessible to Cu(I)-catalyzed azide-alkyne click chemistry. This way, two xanthene-derived photosensitizers were covalently grafted onto the surface of the silanized bacterial cellulose sheets. The obtained materials and photosensitizers were comprehensively characterized by means of FTIR, NMR, elemental analysis, UV/Vis absorption and fluorescence techniques, including nanosecond laser flash photolysis, for the determination of respective triplet state and singlet oxygen quantum yields. The photomicrobicidal activity was tested under white light illumination against gram-negative as well as gram-positive bacteria, including Escherichia coli, Bacillus subtilis and Staphylococcus aureus, as well as fungi (Candida albicans and Aspergillus brasiliensis). The results show type II photochemical antimicrobial activity against S. aureus and B. subtilis, but no effect against gram-negative bacteria and fungi.
KeywordsBacterial cellulose Click chemistry Photocatalysis Singlet oxygen Xanthene dye
The financial support by the Christian Doppler Research Society through the CD-laboratory for “Advanced Cellulose Chemistry and Analytics” and its partner companies is gratefully acknowledged. Lohmann & Rauscher GmbH is additionally acknowledged for providing bacterial cellulose sheets. Dr. Markus Bacher is acknowledged for recording the NMR spectra. We also thank the Marie Curie Program #608407 CYCLON-HIT (FP7-PEOPLE-ITN-2013) as well as the COST Action FP1205 (short-term scientific mission of H.H.).
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