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01.10.2015 | Original Paper

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

verfasst von: Hubert Hettegger, Markus Gorfer, Salvatore Sortino, Aurore Fraix, Dragana Bandian, Christian Rohrer, Wolfgang Harreither, Antje Potthast, Thomas Rosenau

Erschienen in: Cellulose | Ausgabe 5/2015

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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.

Vorheriger Artikel Anti-corrosion behavior of layer by layer coatings of cross-linked chitosan and poly(vinyl butyral) on carbon steel

Nächster Artikel Preparation and characterization of polypyrrole/cellulose fiber conductive composites doped with cationic polyacrylate of different charge density

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Alhajjar RK, Marraiki NAY, Abdel Moaty EA (2014) Comparative study of antimicrobial activities of twotype of TiO₂ nanoparticles against the pathogenic strain of Escherichia coli. Life Sci J 11:982–989

Andresen M, Stenstad P, Moretro T, Langsrud S, Syverud K, Johansson L-S, Stenius P (2007) Nonleaching antimicrobial films prepared from surface-modified microfibrillated cellulose. Biomacromolecules 8:2149–2155. doi:10.1021/bm070304e CrossRef

Arkles B, Steinmetz JR, Zazyczny J, Mehta P (1992) Factors contributing to the stability of alkoxysilanes in aqueous solution. J Adhes Sci Technol 6:193–206. doi:10.1163/156856192x00133 CrossRef

Beghetto C, Renken C, Eriksson O, Jori G, Bernardi P, Ricchelli F (2000) Implications of the generation of reactive oxygen species by photoactivated calcein for mitochondrial studies. Eur J Biochem 267:5585–5592. doi:10.1046/j.1432-1327.2000.01625.x CrossRef

Cao Y, Koo Y-EL, Koo SM, Kopelman R (2005) Ratiometric singlet oxygen nano-optodes and their use for monitoring photodynamic therapy nanoplatforms. Photochem Photobiol 81:1489–1498. doi:10.1562/2005-05-18-ra-532 CrossRef

Chen S-L, Huang X-J, Xu Z-K (2012) Effect of a spacer on phthalocyanine functionalized cellulose nanofiber mats for decolorizing reactive dye wastewater. Cellulose 19:1351–1359. doi:10.1007/s10570-012-9701-9 CrossRef

Cruz-Romero MC, Murphy T, Morris M, Cummins E, Kerry JP (2013) Antimicrobial activity of chitosan, organic acids and nano-sized solubilisates for potential use in smart antimicrobially-active packaging for potential food applications. Food Control 34:393–397. doi:10.1016/j.foodcont.2013.04.042 CrossRef

Dastjerdi R, Montazer M (2010) A review on the application of inorganic nano-structured materials in the modification of textiles: focus on anti-microbial properties. Colloids Surf B 79:5–18. doi:10.1016/j.colsurfb.2010.03.029 CrossRef

Decraene V, Pratten J, Wilson M (2006) Cellulose acetate containing toluidine blue and rose bengal is an effective antimicrobial coating when exposed to white light. Appl Environ Microbiol 72:4436–4439. doi:10.1128/aem.02945-05 CrossRef

DeRosa MC, Crutchley RJ (2002) Photosensitized singlet oxygen and its applications. Coord Chem Rev 233–234:351–371. doi:10.1016/s0010-8545(02)00034-6 CrossRef

Eisenberg WC, Taylor K, Murray RW (1986) Gas-phase kinetics of the reaction of singlet oxygen with olefins at atmospheric pressure. J Phys Chem 90:1945–1948. doi:10.1021/j100400a041 CrossRef

Elchinger P-H, Faugeras P-A, Boens B, Brouillette F, Montplaisir D, Zerrouki R, Lucas R (2011) Polysaccharides: the “click” chemistry impact. Polymers 3:1607–1651. doi:10.3390/polym3041607 CrossRef

Encinas MV, Lemp E, Lissi EA (1987) Interaction of singlet oxygen [O₂(¹Δ)] with aliphatic amines and hydroxylamines. J Chem Soc Perkin Trans 2:1125–1127CrossRef

Fall A, Sene M, Diouf O, Gaye M, Gomez G, Fall Y (2012) Synthesis and use of imidazolium-bound Rose Bengal derivatives for singlet oxygen generation. Open Org Chem J 6:21–26. doi:10.2174/1874095201206010021 CrossRef

Feese E, Sadeghifar H, Gracz HS, Argyropoulos DS, Ghiladi RA (2011) Photobactericidal porphyrin-cellulose nanocrystals: synthesis, characterization, and antimicrobial properties. Biomacromolecules 12:3528–3539. doi:10.1021/bm200718s CrossRef

Fernandes SCM et al (2013) Bioinspired antimicrobial and biocompatible bacterial cellulose membranes obtained by surface functionalization with aminoalkyl groups. ACS Appl Mater Interfaces 5:3290–3297. doi:10.1021/am400338n CrossRef

Fleck CA (2006) Palliative Dilemmas: Wound Odour Wound Care Canada 4:10-13

Garcia G, Naud-Martin D, Carrez D, Croisy A, Maillard P (2011) Microwave-mediated click-chemistry’’ synthesis of glyco-porphyrin derivatives and in vitro photo-cytotoxicity for application in photodynamic therapy. Tetrahedron 67:4924–4932. doi:10.1016/j.tet.2011.04.080 CrossRef

Hajimohammadi M, Safari N, Mofakham H, Shaabani A (2010) A new and efficient aerobic oxidation of aldehydes to carboxylic acids with singlet oxygen in the presence of porphyrin sensitizers and visible light. Tetrahedron Lett 51:4061–4065. doi:10.1016/j.tetlet.2010.05.124 CrossRef

Hettegger H, Kohout M, Mimini V, Lindner W (2014) Novel carbamoyl type quinine and quinidine based chiral anion exchangers implementing alkyne-azide cycloaddition immobilization chemistry. J Chromatogr A 1337:85–94. doi:10.1016/j.chroma.2014.02.026 CrossRef

Hettegger H, Sumerskii I, Sortino S, Potthast A, Rosenau T (2015) Silane meets click chemistry: towards the functionalization of wet bacterial cellulose sheets. ChemSusChem 8:680–687. doi:10.1002/cssc.201402991 CrossRef

Klevens RM, Edwards JR, Richards CL Jr, Horan TC, Gaynes RP, Pollock DA, Cardo DM (2007) Estimating health care-associated infections and deaths in U.S. hospitals, 2002. Public Health Rep 122:160–166

Kosma P (2004) Bacterial polysaccharides: structure and biological activity. In Verein ZELLCHEMING, pp 185–194

Krouit M, Granet R, Branland P, Verneuil B, Krausz P (2006) New photoantimicrobial films composed of porphyrinated lipophilic cellulose esters. Bioorg Med Chem Lett 16:1651–1655. doi:10.1016/j.bmcl.2005.12.008 CrossRef

Krouit M, Bras J, Belgacem MN (2008a) Cellulose surface grafting with polycaprolactone by heterogeneous click-chemistry. Eur Polym J 44:4074–4081. doi:10.1016/j.eurpolymj.2008.09.016 CrossRef

Krouit M, Granet R, Krausz P (2008b) Photobactericidal plastic films based on cellulose esterified by chloroacetate and a cationic porphyrin. Bioorg Med Chem 16:10091–10097. doi:10.1016/j.bmc.2008.10.010 CrossRef

Krouit M, Granet R, Krausz P (2009) Photobactericidal films from porphyrins grafted to alkylated cellulose: synthesis and bactericidal properties. Eur Polym J 45:1250–1259. doi:10.1016/j.eurpolymj.2008.11.036 CrossRef

Kushnir VN, Volyanskii YL, Shevchuk MI (1980) Synthesis and study of the antimicrobial activity of phosphonium salts and ilides containing trichloroethylamide fragments. Khim-Farm Zh 14:45–49

Kushwaha D, Dwivedi P, Kuanar SK, Tiwari VK (2013) Click reaction in carbohydrate chemistry: recent developments and future perspective. Curr Org Synth 10:90–135. doi:10.2174/1570179411310010005 CrossRef

Lenselink E, Andriessen A (2011) A cohort study on the efficacy of a polyhexanide-containing biocellulose dressing in the treatment of biofilms in wounds. J Wound Care 20(534):536–539

Lipovsky A, Nitzan Y, Friedmann H, Lubart R (2009) Sensitivity of Staphylococcus aureus strains to broadband visible light. Photochem Photobiol 85:255–260. doi:10.1111/j.1751-1097.2008.00429.x CrossRef

Liu J-Y, Lo P-C, Jiang X-J, Fong W-P, Ng DKP (2009) Synthesis and in vitro photodynamic activities of di-α-substituted zinc(II) phthalocyanine derivatives. Dalton Trans 21:4129–4135. doi:10.1039/b817940a CrossRef

Lu C, Song G, Lin J-M (2006) Reactive oxygen species and their chemiluminescence-detection methods TrAC. Trends Anal Chem 25:985–995. doi:10.1016/j.trac.2006.07.007 CrossRef

Mbakidi J-P et al (2013) Synthesis and photobiocidal properties of cationic porphyrin-grafted paper. Carbohydr Polym 91:333–338. doi:10.1016/j.carbpol.2012.08.013 CrossRef

Mueller A, Ni Z, Hessler N, Wesarg F, Muller FA, Kralisch D, Fischer D (2013) The biopolymer bacterial nanocellulose as drug delivery system: investigation of drug loading and release using the model protein albumin. J Pharm Sci 102:579–592. doi:10.1002/jps.23385 CrossRef

Pinto RJB, Marques PAAP, Pascoal NC, Trindade T, Daina S, Sadocco P (2009) Antibacterial activity of nanocomposites of silver and bacterial or vegetable cellulosic fibers. Acta Biomater 5:2279–2289. doi:10.1016/j.actbio.2009.02.003 CrossRef

Qin X, Li Y, Zhou F, Ren L, Zhao Y, Yuan X (2015) Polydimethylsiloxane-polymethacrylate block copolymers tethering quaternary ammonium salt groups for antimicrobial coating. Appl Surf Sci 328:183–192. doi:10.1016/j.apsusc.2014.12.019 CrossRef

Ringot C, Sol V, Granet R, Krausz P (2009) Porphyrin-grafted cellulose fabric: new photobactericidal material obtained by “click-chemistry” reaction. Mater Lett 63:1889–1891. doi:10.1016/j.matlet.2009.06.009 CrossRef

Ringot C et al (2011) Triazinyl porphyrin-based photoactive cotton fabrics: preparation, characterization, and antibacterial activity. Biomacromolecules 12:1716–1723. doi:10.1021/bm200082d CrossRef

Schmidt R (2006) Photosensitized generation of singlet oxygen. Photochem Photobiol 82:1161–1177. doi:10.1562/2006-03-03-lR-833 CrossRef

Schweitzer C, Schmidt R (2003) Physical mechanisms of generation and deactivation of singlet oxygen. Chem Rev 103:1685–1757. doi:10.1021/cr010371d CrossRef

Seely GR (1976) Photooxidative destruction of organic wastes. US3951797A

Seybold PG, Gouterman M, Callis J (1969) Calorimetric, photometric, and lifetime determinations of fluorescence yields of fluorescein dyes. Photochem Photobiol 9:229–242. doi:10.1111/j.1751-1097.1969.tb07287.x CrossRef

Spikes JD (1982) Photodynamic reactions in photomedicine. In: Regan J, Parrish J (eds) The science of photomedicine. Photobiology. Springer US pp 113–144. doi:10.1007/978-1-4684-8312-3_5

Tekdas DA, Durmus M, Yanik H, Ahsen V (2012) Photodynamic therapy potential of thiol-stabilized CdTe quantum dot-Group 3A phthalocyanine conjugates (QD-Pc). Spectrochim Acta A 93:313–320. doi:10.1016/j.saa.2012.03.036 CrossRef

Wei B, Yang G, Hong F (2011) Preparation and evaluation of a kind of bacterial cellulose dry films with antibacterial properties. Carbohydr Polym 84:533–538. doi:10.1016/j.carbpol.2010.12.017 CrossRef

X-x Hu, J-p He (2014) Synthesis of anti-microbial agent with silicon quaternary ammonium salt. Yinran 40:13–17

Yang G, Xie J, Deng Y, Bian Y, Hong F (2012) Hydrothermal synthesis of bacterial cellulose/AgNPs composite: a “green” route for antibacterial application. Carbohydr Polym 87:2482–2487. doi:10.1016/j.carbpol.2011.11.017 CrossRef

Zhang X-F, Li X (2011) The photostability and fluorescence properties of diphenylisobenzofuran. J Lumin 131:2263–2266. doi:10.1016/j.jlumin.2011.05.048 CrossRef

Titel: Synthesis, characterization and photo-bactericidal activity of silanized xanthene-modified bacterial cellulose membranes
verfasst von: Hubert Hettegger
Markus Gorfer
Salvatore Sortino
Aurore Fraix
Dragana Bandian
Christian Rohrer
Wolfgang Harreither
Antje Potthast
Thomas Rosenau
Publikationsdatum: 01.10.2015
Verlag: Springer Netherlands
Erschienen in: Cellulose / Ausgabe 5/2015
Print ISSN: 0969-0239
Elektronische ISSN: 1572-882X
DOI: https://doi.org/10.1007/s10570-015-0715-y

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