Effect of different carboxylic acids in cyclodextrin functionalization of cellulose nanocrystals for prolonged release of carvacrol

Materials Science and Engineering C

Volumn 69, Issue , 2016, Pages 1018-1025

  Castro, D O ^a,b   Tabary, N ^c   Martel, B ^c   Gandini, A ^a,b   Belgacem, N ^a,b   Bras, J ^a,b  

^a UNIV GRENOBLE ALPES   (France)

^b CNRS   (France)

^c UNIV LILLE   (France)

Author keywords

Carboxylic acids; Carvacrol; Cellulose nanocrystals; Controlled release; Cyclodextrin

Indexed keywords

CARBOXYLIC ACIDS; CELLULOSE; CELLULOSE DERIVATIVES; CYCLODEXTRINS; INFRARED SPECTROSCOPY; MOLECULES; NANOCRYSTALS; QUARTZ CRYSTAL MICROBALANCES; SURFACE TREATMENT;

ANTI-BACTERIAL ACTIVITY; BACTERIAL ACTIVITY; CARVACROL; CELLULOSE NANO-CRYSTALS; CELLULOSE NANOCRYSTAL (CNC); CONTROLLED RELEASE; NANOCRYSTALLINE CELLULOSE; SURFACE FUNCTIONALIZATION;

GRAFTING (CHEMICAL);

CARBOXYLIC ACIDS; CELLULOSE DERIVATIVES; CYCLODEXTRINS; INFRARED SPECTROSCOPY; SURFACE TREATMENT;

ANTIINFECTIVE AGENT; BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; CARBOXYLIC ACID; CARVACROL; CELLULOSE; DELAYED RELEASE FORMULATION; NANOPARTICLE; PHENOLPHTHALEIN; TERPENE;

ATOMIC FORCE MICROSCOPY; BACILLUS SUBTILIS; CHEMISTRY; DELAYED RELEASE FORMULATION; DRUG EFFECTS; DRUG RELEASE; INFRARED SPECTROSCOPY; MOLECULAR WEIGHT; QUARTZ CRYSTAL MICROBALANCE; TEMPERATURE;

ANTI-BACTERIAL AGENTS; BACILLUS SUBTILIS; BETA-CYCLODEXTRINS; CARBOXYLIC ACIDS; CELLULOSE; DELAYED-ACTION PREPARATIONS; DRUG LIBERATION; MICROSCOPY, ATOMIC FORCE; MOLECULAR WEIGHT; MONOTERPENES; NANOPARTICLES; PHENOLPHTHALEIN; QUARTZ CRYSTAL MICROBALANCE TECHNIQUES; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; TEMPERATURE;

EID: 84982838777     PISSN: 09284931     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.msec.2016.08.014     Document Type: Article

References (39)

1. [1] Gemili, S., Yemenicioğlu, A., Altınkaya, S.A., Development of cellulose acetate based antimicrobial food packaging materials for controlled release of lysozyme. J. Food Eng. 90 (2009), 453–462, 10.1016/j.jfoodeng.2008.07.014.
2. [2] Salmieri, S., Islam, F., Khan, R.a., Hossain, F.M., Ibrahim, H.M.M., Miao, C., Hamad, W.Y., Lacroix, M., Antimicrobial nanocomposite films made of poly(lactic acid)–cellulose nanocrystals (PLA–CNC) in food applications—part B: effect of oregano essential oil release on the inactivation of Listeria monocytogenes in mixed vegetables. Cellulose 21 (2014), 4271–4285, 10.1007/s10570-014-0406-0.
3. [3] Galkina, O.L., Önneby, K., Huang, P., Ivanov, V.K., Agafonov, A.V., Seisenbaeva, G.A., Kessler, V.G., Antibacterial and photochemical properties of cellulose nanofiber–titania nanocomposites loaded with two different types of antibiotic medicines. J. Mater. Chem. B. 3 (2015), 7125–7134, 10.1039/C5TB01382H.
4. [4] Schmeltzer, R.C., Uhrich, K.E., Synthesis and characterization of antiseptic-based poly(anhydride-esters). Polym. Bull. 57 (2006), 281–291, 10.1007/s00289-006-0561-z.
5. [5] Akhlaghi, S.P., Tiong, D., Berry, R.M., Tam, K.C., Comparative release studies of two cationic model drugs from different cellulose nanocrystal derivatives. Eur. J. Pharm. Biopharm. 88 (2014), 207–215, 10.1016/j.ejpb.2014.04.012.
6. [6] Kolakovic, R., Peltonen, L., Laukkanen, A., Hirvonen, J., Laaksonen, T., Nanofibrillar cellulose films for controlled drug delivery. Eur. J. Pharm. Biopharm. 82 (2012), 308–315, 10.1016/j.ejpb.2012.06.011.
7. [7] Credou, J., Berthelot, T., Cellulose: from biocompatible to bioactive material. J. Mater. Chem. B., 2, 2014, 4767, 10.1039/C4TB00431K.
8. [8] Jebali, A., Yasini Ardakani, S.A., Shahdadi, H., Balal Zadeh, M.H., Hekmatimoghaddam, S., Modification of nanocellulose by poly-lysine can inhibit the effect of fumonisin B1 on mouse liver cells. Colloids Surf. B: Biointerfaces 126 (2015), 437–443, 10.1016/j.colsurfb.2014.12.047.
9. [9] Zhang, C., Salick, M.R., Cordie, T.M., Ellingham, T., Dan, Y., Turng, L., Incorporation of poly (ethylene glycol) grafted cellulose nanocrystals in poly (lactic acid) electrospun nanocomposite fi bers as potential scaffolds for bone tissue engineering. Mater. Sci. Eng. C 49 (2015), 463–471.
10. [10] Jonoobi, M., Oladi, R., Davoudpour, Y., Oksman, K., Dufresne, A., Hamzeh, Y., Davoodi, R., Different preparation methods and properties of nanostructured cellulose from various natural resources and residues: a review. Cellulose 22 (2015), 935–969, 10.1007/s10570-015-0551-0.
11. [11] Flauzino Neto, W.P., Silvério, H.A., Dantas, N.O., Pasquini, D., Extraction and characterization of cellulose nanocrystals from agro-industrial residue – soy hulls. Ind. Crop. Prod. 42 (2013), 480–488, 10.1016/j.indcrop.2012.06.041.
12. [12] Siqueira, G., Tapin-Lingua, S., Bras, J., da Silva Perez, D., Dufresne, A., Morphological investigation of nanoparticles obtained from combined mechanical shearing, and enzymatic and acid hydrolysis of sisal fibers. Cellulose 17 (2010), 1147–1158, 10.1007/s10570-010-9449-z.
13. [13] Jorfi, M., Foster, E.J., Recent advances in nanocellulose for biomedical applications. J. Appl. Polym. Sci., 132, 2014, 10.1002/app.41719 (n/a–n/a).
14. [14] Eyley, S.S., Thielemans, W., Surface modification of cellulose nanocrystals. Nanoscale 6 (2014), 7764–7779, 10.1039/c4nr01756k.
15. [15] Peila, R., Vineis, C., Varesano, A., Ferri, A., Different methods for β-cyclodextrin/triclosan complexation as antibacterial treatment of cellulose substrates. Cellulose 20 (2013), 2115–2123, 10.1007/s10570-013-9967-6.
16. [16] Uekama, K., Hirayama, F., Irie, T., Cyclodextrin drug carrier systems. Chem. Rev. 98 (1998), 2045–2076, 10.1021/cr970025p (ST – Cyclodextrin Drug Carrier Systems).
17. [17] Del Valle, E.M.M., Cyclodextrins and their uses: a review. Process Biochem. 39 (2004), 1033–1046, 10.1016/S0032-9592(03)00258-9.
18. [18] Lavoine, N., Givord, C., Tabary, N., Desloges, I., Martel, B., Bras, J., Elaboration of a new antibacterial bio-nano-material for food-packaging by synergistic action of cyclodextrin and microfibrillated cellulose. Innovative Food Sci. Emerg. Technol. 26 (2014), 330–340, 10.1016/j.ifset.2014.06.006.
19. [19] Davis, M.E., Brewster, M.E., Cyclodextrin-based pharmaceutics: past, present and future. Nat. Rev. Drug Discov. 3 (2004), 1023–1035, 10.1038/nrd1576.
20. [20] Kotan, R., Cakir, A., Dadasoglu, F., Aydin, T., Cakmakci, R., Ozer, H., Kordali, S., Mete, E., Dikbas, N., Antibacterial activities of essential oils and extracts of Turkish Achillea, Satureja and Thymus species against plant pathogenic bacteria. J. Sci. Food Agric. 90 (2010), 145–160, 10.1002/jsfa.3799.
21. [21] Todan, L., Voicescu, M., Ciuculescu, C., Maganu, M., A way for improving the stability of the essential oils in an environmental friendly formulation. Mater. Sci. Eng. C 33 (2013), 3281–3288.
22. [22] Lima, M.D.S., Quintans-Júnior, L.J., de Santana, W.A., Martins Kaneto, C., Pereira Soares, M.B., Villarreal, C.F., Anti-inflammatory effects of carvacrol: evidence for a key role of interleukin-10. Eur. J. Pharmacol. 699 (2013), 112–117, 10.1016/j.ejphar.2012.11.040.
23. [23] Cusola, O., Tabary, N., Belgacem, M.N., Bras, J., Cyclodextrin functionalization of several cellulosic substrates for prolonged release of antibacterial agents. J. Appl. Polym. Sci. 129 (2013), 604–613, 10.1002/app.38748.
24. [24] Dong, C., Ye, Y., Qian, L., Zhao, G., He, B., Xiao, H., Antibacterial modification of cellulose fibers by grafting β-cyclodextrin and inclusion with ciprofloxacin. Cellulose 21 (2014), 1921–1932, 10.1007/s10570-014-0249-8.
25. [25] Mäkelä, M., Korpela, T., Laakso, S., Colorimetric determination of β-cyclodextrin: two assay modifications based on molecular complexation of phenolphatalein. J. Biochem. Biophys. Methods 14 (1987), 85–92, 10.1016/0165-022X(87)90043-1.
26. [26] Sain, M., Panthapulakkal, S., Bioprocess preparation of wheat straw fibers and their characterization. Ind. Crop. Prod. 23 (2006), 1–8, 10.1016/j.indcrop.2005.01.006.
27. [27] Baiardo, M., Frisoni, G., Scandola, M., Rimelen, M., Lips, D., Ruffieux, K., Wintermantel, E., Thermal and mechanical properties of plasticized poly(L-lactic acid). J. Appl. Polym. Sci. 90 (2003), 1731–1738, 10.1002/app.12549.
28. [28] Medronho, B., Andrade, R., Vivod, V., Ostlund, A., Miguel, M.G., Lindman, B., Voncina, B., Valente, A.J.M., Cyclodextrin-grafted cellulose: physico-chemical characterization. Carbohydr. Polym. 93 (2013), 324–330, 10.1016/j.carbpol.2012.08.109.
29. [29] Espino-Pérez, E., Domenek, S., Belgacem, N., Sillard, C., Bras, J., Green process for chemical functionalization of nanocellulose with carboxylic acids. Biomacromolecules 15 (2014), 4551–4560, 10.1021/bm5013458.
30. [30] Narayanan, G., Gupta, B.S., Tonelli, A.E., Poly(ε-caprolactone) nanowebs functionalized with α- and γ-cyclodextrins. Biomacromolecules 15 (2014), 4122–4133, 10.1021/bm501158w.
31. [31] Basappa, C., Rao, P., Rao, D.N., Divakar, S., A modified colorimetric method for the estimation of beta cyclodextrin using phenolphthalein. Int. J. Food Sci. Technol. 33 (1998), 517–520, 10.1046/j.1365-2621.1998.00216.x.
32. [32] Carlsson, L., Utsel, S., Wågberg, L., Malmström, E., Carlmark, A., Surface-initiated ring-opening polymerization from cellulose model surfaces monitored by a Quartz Crystal Microbalance. Soft Matter, 8, 2012, 512, 10.1039/c1sm06121f.
33. [33] Bardet, R., Belgacem, N., Bras, J., Flexibility and color monitoring of cellulose nanocrystal iridescent solid films using anionic or neutral polymers. ACS Appl. Mater. Interfaces 7 (2015), 4010–4018, 10.1021/am506786t.
34. [34] De Castro, D.O., Bras, J., Gandini, A., Belgacem, N., Surface grafting of cellulose nanocrystals with natural antimicrobial rosin mixture using a green process. Carbohydr. Polym. 137 (2016), 1–8, 10.1016/j.carbpol.2015.09.101.
35. [35] Ehmann, H.M.A., Mohan, T., Koshanskaya, M., Scheicher, S., Breitwieser, D., Ribitsch, V., Stana-Kleinschek, K., Spirk, S., Design of anticoagulant surfaces based on cellulose nanocrystals. Chem. Commun. (Camb.) 50 (2014), 13070–13072, 10.1039/c4cc05254d.
36. [36] Saini, S., Sillard, C., Belgacem, M.N., Bras, J., Nisin anchored cellulose nanofibers for long term antimicrobial active food packaging. Rsc Adv. 6 (2016), 12437–12445, 10.1039/c5ra22748h.
37. [37] Santos, E.H., Kamimura, J.a., Hill, L.E., Gomes, C.L., Characterization of carvacrol beta-cyclodextrin inclusion complexes as delivery systems for antibacterial and antioxidant applications. LWT Food Sci. Technol. 60 (2015), 583–592, 10.1016/j.lwt.2014.08.046.
38. [38] Ben Arfa, A., Combes, S., Gontard, N., Chalier, P., Antimicrobial activity of carvacrol related to its chemical structure. Lett. Appl. Microbiol. 43 (2006), 149–154, 10.1111/j.1472-765X.2006.01938.x.
39. [39] Nostro, A., Nostro, A., Papalia, T., Antimicrobial activity of carvacrol: current progress and future prospectives. Recent. Pat. Antiinfect. Drug Discov., 2011, 10.2174/157489112799829684.