Abstract
Oxidized cellulose nanocrystals with sodium carboxylate groups (TOCNC-COONa) and with free carboxyl groups (TOCN-COOH) were prepared and then chemically modified with beta-cyclodextrin (βCD) and hydroxypropyl-beta-cyclodextrin (HPβCD) to prepare materials able to load and release antibacterial molecules over a prolonged period of time. The materials were characterized by infrared spectroscopy, and the CD content of modified TOCNCs determined by phenolphthalein colorimetry. The extent of grafting was also assessed by QCM-D and microscopy was used to ascertain and compare the morphology of both TOCNC-COONa/HPβCD and TOCNC-COOH/HPβCD. Then, carvacrol and curcumin were entrapped by the attached HPβCD and their prolonged release confirmed, as compared to neat material. The combined effects of HPβCD and carvacrol on the antimicrobial properties of TOCNC-COOH films were finally evaluated.
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References
Alila S, Besbes I, Vilar MR et al (2013) Non-woody plants as raw materials for production of microfibrillated cellulose (MFC): a comparative study. Ind Crops Prod 41:250–259. https://doi.org/10.1016/j.indcrop.2012.04.028
Astray G, Gonzalez-Barreiro C, Mejuto JC et al (2009) A review on the use of cyclodextrins in foods. Food Hydrocoll 23:1631–1640. https://doi.org/10.1016/j.foodhyd.2009.01.001
Azzam F, Heux L, Jean B, Putaux J-L (2010) Preparation by grafting onto, characterization and properties of thermally responsive polymer-decorated cellulose nanocrystals. Biomacromolecules 11:3652–3659. https://doi.org/10.1021/bm101106c
Bakkour Y, Vermeersch G, Morcellet M et al (2006) Formation of cyclodextrin inclusion complexes with doxycyclin-hyclate: NMR investigation of their characterisation and stability. J Incl Phenom Macrocycl Chem 54:109–114. https://doi.org/10.1007/s10847-005-5108-7
Barba C, Eguinoa A, Mate JI (2015) Preparation and characterization of β-cyclodextrin inclusion complexes as a tool of a controlled antimicrobial release in whey protein edible films. LWT Food Sci Technol 64:1362–1369. https://doi.org/10.1016/j.lwt.2015.07.060
Butchosa NN, Brown C, Larsson PT et al (2013) Nanocomposites of bacterial cellulose nanofibers and chitin nanocrystals: fabrication, characterization and bactericidal activity. Green Chem 15:3404. https://doi.org/10.1039/c3gc41700j
Castro DO, Tabary N, Martel B et al (2016) Effect of different carboxylic acids in cyclodextrin functionalization of cellulose nanocrystals for prolonged release of carvacrol. Mater Sci Eng C 69:1018–1025. https://doi.org/10.1016/j.msec.2016.08.014
Chen G, Liu B (2016) Cellulose sulfate based film with slow-release antimicrobial properties prepared by incorporation of mustard essential oil and β-cyclodextrin. Food Hydrocoll 55:100–107. https://doi.org/10.1016/j.foodhyd.2015.11.009
da Silva Perez D, Montanari S, Vignon MR (2003) TEMPO-mediated oxidation of cellulose III. Biomacromolecules 4:1417–1425. https://doi.org/10.1021/bm034144s
Dehabadi VA, Buschmann H-J, Gutmann JS (2014) Spectrophotometric estimation of the accessible inclusion sites of β-cyclodextrin fixed on cotton fabrics using phenolic dyestuffs. Anal Methods 6:3382. https://doi.org/10.1039/c4ay00293h
Dong C, Ye Y, Qian L et al (2014) Antibacterial modification of cellulose fibers by grafting β-cyclodextrin and inclusion with ciprofloxacin. Cellulose 21:1921–1932. https://doi.org/10.1007/s10570-014-0249-8
Du YZ, Xu JG, Wang L et al (2009) Preparation and characteristics of hydroxypropyl-β-cyclodextrin polymeric nanocapsules loading nimodipine. Eur Polym J 45:1397–1402. https://doi.org/10.1016/j.eurpolymj.2009.01.031
Ehmann HMA, Mohan T, Koshanskaya M et al (2014) Design of anticoagulant surfaces based on cellulose nanocrystals. Chem Commun (Camb) 50:13070–13072. https://doi.org/10.1039/c4cc05254d
Espino-Pérez E, Bras J, Almeida G et al (2016) Cellulose nanocrystal surface functionalization for the controlled sorption of water and organic vapours. Cellulose 23:2955–2970. https://doi.org/10.1007/s10570-016-0994-y
Fujisawa S, Okita Y, Fukuzumi H et al (2011) Preparation and characterization of TEMPO-oxidized cellulose nanofibril films with free carboxyl groups. Carbohydr Polym 84:579–583. https://doi.org/10.1016/j.carbpol.2010.12.029
Gandini A, Belgacem N (2015) The surface and in-depth modification of cellulose fibers. In: Rojas OJ (ed) Cellulose chemistry and properties: fibers, nanocelluloses and advanced materials, 1st edn. Springer, Berlin, pp 169–206
Garcia A, Gandini A, Labidi J et al (2016) Industrial and crop wastes: a new source for nanocellulose biorefinery. Ind Crops Prod 93:26–38. https://doi.org/10.1016/j.indcrop.2016.06.004
Gicquel E, Martin C, Garrido Yanez J, Bras J (2017) Cellulose nanocrystals as new bio-based coating layer for improving fiber-based mechanical and barrier properties. J Mater Sci 52:3048–3061. https://doi.org/10.1007/s10853-016-0589-x
Gómez HC, Serpa A, Velásquez-Cock J et al (2016) Vegetable nanocellulose in food science: a review. Food Hydrocoll 57:178–186. https://doi.org/10.1016/j.foodhyd.2016.01.023
Habibi Y, Chanzy H, Vignon MR (2006) TEMPO-mediated surface oxidation of cellulose whiskers. Cellulose 13:679–687. https://doi.org/10.1007/s10570-006-9075-y
Hegge AB, Vukicevic M, Bruzell E et al (2013) Solid dispersions for preparation of phototoxic supersaturated solutions for antimicrobial photodynamic therapy (aPDT): studies on curcumin and curcuminoides L. Eur J Pharm Biopharm 83:95–105. https://doi.org/10.1016/j.ejpb.2012.09.011
Higueras L, López-carballo G, Cerisuelo JP, Gavara R (2013) Preparation and characterization of chitosan/HP-β-cyclodextrins composites with high sorption capacity for carvacrol. Carbohydr Polym 97:262–268. https://doi.org/10.1016/j.carbpol.2013.04.007
Kayaci F, Ertas Y, Uyar T (2013) Enhanced thermal stability of eugenol by cyclodextrin inclusion complex encapsulated in electrospun polymeric nanofibers. J Agric Food Chem 61:8156–8165. https://doi.org/10.1021/jf402923c
Kfoury M, Landy D, Ruellan S et al (2016) Determination of formation constants and structural characterization of cyclodextrin inclusion complexes with two phenolic isomers: carvacrol and thymol. Beilstein J Org Chem 12:29–42. https://doi.org/10.3762/bjoc.12.5
Kurek M, Moundanga S, Favier C et al (2013) Antimicrobial efficiency of carvacrol vapour related to mass partition coefficient when incorporated in chitosan based films aimed for active packaging. Food Control 32:168–175
La A, Ercolini D, Marinello F et al (2011) Atomic force microscopy analysis shows surface structure changes in carvacrol-treated bacterial cells. Res Microbiol 162:164–172. https://doi.org/10.1016/j.resmic.2010.11.006
Lavoine N, Givord C, Tabary N et al (2014a) Elaboration of a new antibacterial bio-nano-material for food-packaging by synergistic action of cyclodextrin and microfibrillated cellulose. Innov Food Sci Emerg Technol 26:330–340. https://doi.org/10.1016/j.ifset.2014.06.006
Lavoine N, Tabary N, Desloges I et al (2014b) Controlled release of chlorhexidine digluconate using β-cyclodextrin and microfibrillated cellulose. Colloids Surf B Biointerfaces 121:196–205. https://doi.org/10.1016/j.colsurfb.2014.06.021
Li B, Konecke S, Wegiel LA et al (2013) Both solubility and chemical stability of curcumin are enhanced by solid dispersion in cellulose derivative matrices. Carbohydr Polym 98:1108–1116. https://doi.org/10.1016/j.carbpol.2013.07.017
Lin N, Dufresne A (2013) Supramolecular hydrogels from in situ host–guest inclusion between chemically modified cellulose nanocrystals and cyclodextrin. Biomacromolecules 14:871–880. https://doi.org/10.1021/bm301955k
Lin N, Dufresne A (2014) Nanocellulose in biomedicine: current status and future prospect. Eur Polym J 59:302–325. https://doi.org/10.1016/j.eurpolymj.2014.07.025
Mäkelä M, Korpela T, Laakso S (1987) Colorimetric determination of β-cyclodextrin: two assay modifications based on molecular complexation of phenolphthalein. J Biochem Biophys Methods 14:85–92. https://doi.org/10.1016/0165-022X(87)90043-1
Marcolino VA, Zanin GM, Durrant LR et al (2011) Interaction of curcumin and bixin with β-cyclodextrin: complexation methods, stability, and applications in food. J Agric Food Chem 59:3348–3357. https://doi.org/10.1021/jf104223k
Mohamed MH, Wilson LD, Headley JV (2010) Estimation of the surface accessible inclusion sites of β-cyclodextrin based copolymer materials. Carbohydr Polym 80:186–196. https://doi.org/10.1016/j.carbpol.2009.11.014
Mulinacci N, Melani F, Vincieri FF et al (1996) 1H-NMR NOE and molecular modelling to characterize thymol and carvacrol β-cyclodextrin complexes. Int J Pharm 128:81–88. https://doi.org/10.1016/0378-5173(95)04224-5
Peretto G, Du W, Avena-bustillos RJ et al (2014) Postharvest Biology and Technology Increasing strawberry shelf-life with carvacrol and methyl cinnamate antimicrobial vapors released from edible films. 89:11–18. https://doi.org/10.1016/j.postharvbio.2013.11.003
Piercey MJ, Mazzanti G, Budge SM et al (2012) Antimicrobial activity of cyclodextrin entrapped allyl isothiocyanate in a model system and packaged fresh-cut onions. Food Microbiol 30:213–218. https://doi.org/10.1016/j.fm.2011.10.015
Ponce Cevallos PA, Buera MP, Elizalde BE (2010) Encapsulation of cinnamon and thyme essential oils components (cinnamaldehyde and thymol) in β-cyclodextrin: effect of interactions with water on complex stability. J Food Eng 99:70–75. https://doi.org/10.1016/j.jfoodeng.2010.01.039
Saito T, Isogai A (2004) TEMPO-mediated oxidation of native cellulose. The effect of oxidation conditions on chemical and crystal structures of the water-insoluble fractions. Biomacromolecules 5:1983–1989. https://doi.org/10.1021/bm0497769
Sanchez-Gonzalez L, Gonzalez-Martinez C, Chiralt A, Chafer M (2010) Physical and antimicrobial properties of chitosan-tea tree essential oil composite films. J Food Eng 98:443–452. https://doi.org/10.1016/j.jfoodeng.2010.01.026
Siepmann J, Siepmann F (2012) Modeling of diffusion controlled drug delivery. J Control Release 161:351–362. https://doi.org/10.1016/j.jconrel.2011.10.006
Sun Y, Du L, Liu Y et al (2014) Transdermal delivery of the in situ hydrogels of curcumin and its inclusion complexes of hydroxypropyl-β-cyclodextrin for melanoma treatment. Int J Pharm 469:31–39. https://doi.org/10.1016/j.ijpharm.2014.04.039
Tomren MA, Másson M, Loftsson T, Tønnesen HH (2007) Studies on curcumin and curcuminoids. XXXI. Symmetric and asymmetric curcuminoids: stability, activity and complexation with cyclodextrin. Int J Pharm 338:27–34. https://doi.org/10.1016/j.ijpharm.2007.01.013
Valo H, Arola S, Laaksonen P et al (2013) Drug release from nanoparticles embedded in four different nanofibrillar cellulose aerogels. Eur J Pharm Sci 50:69–77. https://doi.org/10.1016/j.ejps.2013.02.023
Veiga FJ, Fernandes CM, Carvalho RA, Geraldes CF (2001) Molecular modelling and 1H-NMR: ultimate tools for the investigation of tolbutamide: beta-cyclodextrin and tolbutamide: hydroxypropyl-beta-cyclodextrin complexes. Chem Pharm Bull (Tokyo) 49:1251–1256. https://doi.org/10.1248/cpb.49.1251
Wang D-C, Yu H-Y, Song M-L et al (2017) Superfast adsorption-disinfection cryogels decorated with cellulose nanocrystal/zinc oxide nanorod clusters for water-purifying microdevices. ACS Sustain Chem Eng 5:6776–6785. https://doi.org/10.1021/acssuschemeng.7b01029
Yu H, Yan C, Yao J (2014) Fully biodegradable food packaging materials based on functionalized cellulose nanocrystals/poly(3-hydroxybutyrate-co-3-hydroxyvalerate) nanocomposites. RSC Adv 4:59792–59802. https://doi.org/10.1039/C4RA12691B
Yu HY, Zhang DZ, Lu FF, Yao J (2016) New approach for single-step extraction of carboxylated cellulose nanocrystals for their use as adsorbents and flocculants. ACS Sustain Chem Eng 4:2632–2643. https://doi.org/10.1021/acssuschemeng.6b00126
Zarzycki PK, Lamparczyk H (1998) The equilibrium constant of β-cyclodextrin–phenolphthalein complex; influence of temperature and tetrahydrofuran addition 1. J Pharm Biomed Anal 18:165–170
Acknowledgments
The authors gratefully acknowledge the CNPq (National Research Council, Brazil) for the postdoctoral fellowship to D.O.C. (248642/2013-8) and to Dr. Marcos Mariano for the support with AFM data. LGP2 is part of the LabEx Tec 21 (Investissements d’Avenir—Grant Agreement No. ANR-11-LABX-0030) and of the Énergies du Futur and PolyNat Carnot Institutes (Investissements d’Avenir—Grant Agreements No. ANR-11-CARN-007-01 and ANR-11-CARN-030-01).
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de Castro, D.O., Tabary, N., Martel, B. et al. Controlled release of carvacrol and curcumin: bio-based food packaging by synergism action of TEMPO-oxidized cellulose nanocrystals and cyclodextrin. Cellulose 25, 1249–1263 (2018). https://doi.org/10.1007/s10570-017-1646-6
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DOI: https://doi.org/10.1007/s10570-017-1646-6