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

被引:38
作者
Castro, D. O. [1 ,2 ]
Tabary, N. [3 ]
Martel, B. [3 ]
Gandini, A. [1 ,2 ]
Belgacem, N. [1 ,2 ]
Bras, J. [1 ,2 ]
机构
[1] Univ Grenoble Alpes, LGP2, F-38000 Grenoble, France
[2] CNRS, LGP2, F-38000 Grenoble, France
[3] Univ Lille 1, Unite Mat & Transformat UMET, UMR CNRS 8207, F-59655 Villeneuve Dascq, France
来源
MATERIALS SCIENCE & ENGINEERING C-MATERIALS FOR BIOLOGICAL APPLICATIONS | 2016年 / 69卷
关键词
Cellulose nanocrystals; beta-Cyclodextrin; Carboxylic acids; Carvacrol; Controlled release; BETA-CYCLODEXTRIN; ANTIBACTERIAL; FIBERS; FILMS; NANOCELLULOSE; COMPLEXATION; INCLUSION;
D O I
10.1016/j.msec.2016.08.014
中图分类号
TB3 [工程材料学]; R318.08 [生物材料学];
学科分类号
0805 ; 080501 ; 080502 ;
摘要
Current investigations deal with new surface functionalization strategy of nanocrystalline cellulose-based substrates to impart active molecule release properties. In this study, cellulose nanocrystals (CNC) were surface-functionalized with P-cyclodextrin (beta-CD) using succinic acid (SA) and fumaric acid (FA) as bridging agents. The main objective of this surface modification performed only in aqueous media was to obtain new active materials able to release antibacterial molecules over a prolonged period of time. The reactions were conducted by immersing the CNC film into a solution composed of beta-CD, SA and FA, leading to CNC grafting. The materials were characterized by infrared spectroscopy (FT-IR), Quartz crystal microbalance-dissipation (QCM-D), AFM and phenolphthalein (PhP) was used to determine the efficiency of CNC grafting with beta-CD. The results indicated that p CD was successfully attached to the CNC backbone through the formation of ester bonds. Furthermore, carvacrol was entrapped by the attached beta-CD and a prolonged release was confirmed. In particular, CNC grafted to p-a) in the presence of FA was selected as the best solution. The antibacterial activity and the controlled release were studied for this sample. Considerably longer bacterial activity against B. subtilis was observed for CNC grafted to beta-CD compared to CNC and CNC-FA, confirming the promising impact of the present strategy. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码:1018 / 1025
页数:8
相关论文
共 39 条
[1]   Comparative release studies of two cationic model drugs from different cellulose nanocrystal derivatives [J].
Akhlaghi, Seyedeh Parinaz ;
Tiong, Daryl ;
Berry, Richard M. ;
Tam, Kam Chiu .
EUROPEAN JOURNAL OF PHARMACEUTICS AND BIOPHARMACEUTICS, 2014, 88 (01) :207-215
[2]   Thermal and mechanical properties of plasticized poly(L-lactic acid) [J].
Baiardo, M ;
Frisoni, G ;
Scandola, M ;
Rimelen, M ;
Lips, D ;
Ruffieux, K ;
Wintermantel, E .
JOURNAL OF APPLIED POLYMER SCIENCE, 2003, 90 (07) :1731-1738
[3]   Flexibility and Color Monitoring of Cellulose Nanocrystal Iridescent Solid Films Using Anionic or Neutral Polymers [J].
Bardet, Raphael ;
Belgacem, Naceur ;
Bras, Julien .
ACS APPLIED MATERIALS & INTERFACES, 2015, 7 (07) :4010-4018
[4]   A modified colorimetric method for the estimation of β-cyclodextrin using phenolphthalein [J].
Basappa, C ;
Rao, P ;
Rao, DN ;
Divakar, S .
INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY, 1998, 33 (06) :517-520
[5]   Antimicrobial activity of carvacrol related to its chemical structure [J].
Ben Arfa, A. ;
Combes, S. ;
Preziosi-Belloy, L. ;
Gontard, N. ;
Chalier, P. .
LETTERS IN APPLIED MICROBIOLOGY, 2006, 43 (02) :149-154
[6]   Surface-initiated ring-opening polymerization from cellulose model surfaces monitored by a Quartz Crystal Microbalance [J].
Carlsson, Linn ;
Utsel, Simon ;
Wagberg, Lars ;
Malmstrom, Eva ;
Carlmark, Anna .
SOFT MATTER, 2012, 8 (02) :512-517
[7]   Cellulose: from biocompatible to bioactive material [J].
Credou, Julie ;
Berthelot, Thomas .
JOURNAL OF MATERIALS CHEMISTRY B, 2014, 2 (30) :4767-4788
[8]   Cyclodextrin functionalization of several cellulosic substrates for prolonged release of antibacterial agents [J].
Cusola, Oriol ;
Tabary, Nicolas ;
Belgacem, Mohamed Naceur ;
Bras, Julien .
JOURNAL OF APPLIED POLYMER SCIENCE, 2013, 129 (02) :604-613
[9]   Cyclodextrin-based pharmaceutics: Past, present and future [J].
Davis, ME ;
Brewster, ME .
NATURE REVIEWS DRUG DISCOVERY, 2004, 3 (12) :1023-1035
[10]   Surface grafting of cellulose nanocrystals with natural antimicrobial rosin mixture using a green process [J].
de Castro, Daniele Oliveira ;
Bras, Julien ;
Gandini, Alessandro ;
Belgacem, Naceur .
CARBOHYDRATE POLYMERS, 2016, 137 :1-8