Cellulose

, Volume 22, Issue 5, pp 3291–3304 | Cite as

Synthesis, characterization and photo-bactericidal activity of silanized xanthene-modified bacterial cellulose membranes

  • Hubert Hettegger
  • Markus Gorfer
  • Salvatore Sortino
  • Aurore Fraix
  • Dragana Bandian
  • Christian Rohrer
  • Wolfgang Harreither
  • Antje Potthast
  • Thomas Rosenau
Original Paper

Abstract

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.

Keywords

Bacterial cellulose Click chemistry Photocatalysis Singlet oxygen Xanthene dye 

Abbreviations

BC

Bacterial cellulose

APTES

(3-Azidopropyl)triethoxysilane

DPBF

1,3-Diphenylisobenzofuran

PS

Photosensitizer

DBB

o-Dibenzoylbenzene

Notes

Acknowledgments

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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Copyright information

© Springer Science+Business Media Dordrecht 2015

Authors and Affiliations

  • Hubert Hettegger
    • 1
  • Markus Gorfer
    • 2
    • 3
  • Salvatore Sortino
    • 4
  • Aurore Fraix
    • 4
  • Dragana Bandian
    • 2
  • Christian Rohrer
    • 5
  • Wolfgang Harreither
    • 5
  • Antje Potthast
    • 1
  • Thomas Rosenau
    • 1
    • 6
  1. 1.Division of Chemistry of Renewable Resources, Christian-Doppler Laboratory “Advanced Cellulose Chemistry and Analytics”, Department of ChemistryUniversity of Natural Resources and Life Sciences Vienna (BOKU)TullnAustria
  2. 2.Bioresources UnitAIT - Austrian Institute of Technology GmbHTullnAustria
  3. 3.Fungal Genetics and Genomics Unit, Department of Applied Genetics and Cell BiologyUniversity of Natural Resources and Life Sciences Vienna (BOKU)TullnAustria
  4. 4.Division of Chemistry, Department of Drug SciencesUniversity of CataniaCataniaItaly
  5. 5.Lohmann & Rauscher GmbH & Co. KGNeuwiedGermany
  6. 6.ViennaAustria

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