Preparation and Sustained-Release Property of Chitosan Maleate Hydrogel with pH Response

LI Ying; LI Xu; WANG Hongling; CHEN Siyuan; DING Junyang; LIU Changxia

doi:10.13386/j.issn1002-0306.2022120149

Volume 44 Issue 20

Oct. 2023

Turn off MathJax

Article Contents

Abstract

References

Science and Technology of Food Industry > 2023 > 44(20): 250-256. > DOI: 10.13386/j.issn1002-0306.2022120149

LI Ying, LI Xu, WANG Hongling, et al. Preparation and Sustained-Release Property of Chitosan Maleate Hydrogel with pH Response[J]. Science and Technology of Food Industry, 2023, 44(20): 250−256. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2022120149.

Citation:

PDF (2960 KB)

Preparation and Sustained-Release Property of Chitosan Maleate Hydrogel with pH Response

Department of Chemistry and Chemical Engineering, Cangzhou Normal University, Cangzhou 061000, China

More Information

Received Date: December 17, 2022
Available Online: August 01, 2023

Graphical Abstract

Abstract

Abstract

Chitosan hydrogel (CS–Ma–Gel) was constructed by ionic crosslinking of maleic acid. Taking Amoxicillin (Am) as the model drug, the drug loaded hydrogel (Am/CS-Ma-Gel) was prepared. The structure and morphology of the hydrogels were characterized by FT-IR, UV-Vis, SEM and so on. The swelling property and drug sustained release behavior for the hydrogels were investigated in different pH media. The experiment results indicated that Am was uniformly dispersed in CS–Ma–Gel hydrogel network without phase separation. Both the swelling property and Am sustained release behavior for the hydrogels exhibited pH responsiveness. In pH 2.00, 4.00, 6.86 and 9.18 media, the swelling rates of CS-Ma-Gel were 800%, 2200%, 760% and 1300%, respectively. Cumulative drug release rates of Am/CS-Ma-Gel were 24.6%, 70.4%, 35.7% and 50.4% for 42 h, respectively. The swelling rate and drug cumulative release rate in acidic and alkaline media were higher than those in neutral media, and the drug release capacity was positively correlated with the swelling property. The preparation method of Am/CS–Ma–Gel is simple and green. Am/CS–Ma–Gel shows the characteristics of amphoteric ionic pH-responsive hydrogel. The research lays a theory and experiment foundation for the development of chitosan sustained release materials.
- chitosan maleate,
- hydrogel,
- pH responsiveness,
- swelling,
- sustained release

FullText(HTML)

References (33)

References

[1]	CHANG H, LI C X, HUANG R L, et al. Amphiphilic hydrogels for biomedical applications[J]. Journal of Materials Chemistry B,2019,7(18):2899−2910. doi: 10.1039/C9TB00073A
[2]	GUYOT C, CERRUTI M, LEROUGE S. Injectable, strong and bioadhesive catechol–chitosan hydrogels physically crosslinked using sodium bicarbonate[J]. Materials Science & Engineering C–Materials for Biological Applications,2021,118(1):111529.
[3]	KARIMI A R, ROSTAMINEJAD B, RAHIMI L, Chitosan hydrogels cross–linked with tris (2-(2-formylphenoxy) ethyl) amine: swelling and drug delivery[J]. International Journal of Biological Macromolecules, 2018, 118: 1863–1870.
[4]	SHARMA S, NANDAN G, ROHATGI P K, et al. Recent advances in self–healing materials[J]. Materials Today,2019,18:4729−4737.
[5]	蔡紫煊, 张斌, 姜丽阳, 等. 智能响应型水凝胶药物控释体系及其应用[J]. 化学进展,2019,31(12):1653−1668. [CAI Z X, ZHANG B, JIANG L Y, et al. Intelligent responsive hydrogels based controlled drug release systems and its applications[J]. Progress in Chemistry,2019,31(12):1653−1668. CAI Z X, ZHANG B, JIANG L Y, et al. Intelligent responsive hydrogels based controlled drug release systems and its applications[J]. Progress in Chemistry, 2019, 31(12): 1653–1668.
[6]	DING F Y, LI H B, DU Y M, et al. Recent advances in chitosan–based self–healing materials[J]. Research on Chemical Intermediates,2018,44(8):4827−4840. doi: 10.1007/s11164-018-3339-7
[7]	LI L, ZHANG P, LI C C, et al. In vitro/vivo antitumor study of modified–chitosan/ carboxymethyl chitosan “boosted” charge-reversal nanoformulation[J]. Carbohydrate Polymers,2021,269:118268. doi: 10.1016/j.carbpol.2021.118268
[8]	梁晓云, 赵王晨, 张晨, 等. 壳聚糖/EGCG@MNPs纳米复合包装对低温和常温贮藏蓝莓保鲜效果的影响[J]. 食品工业科技,2022,43(24):268−279. [LIANG X Y, ZHAO W C, ZHANG C, et al. Effects of chitosan/EGCG@MNPs nanocomposite packaging on preservation of blueberries stored at low temperature and normal temperature[J]. Science and Technology of Food Industry,2022,43(24):268−279. LIANG X Y, ZHAO W C, ZHANG C, et al. Effects of chitosan/EGCG@MNPs nanocomposite packaging on preservation of blueberries stored at low temperature and normal temperature[J]. Science and Technology of Food Industry, 2022, 43(24): 268-279.
[9]	黄承都, 艾硕, 刘纯友, 等. 壳聚糖/活性白土糖用复合脱色剂的制备及其吸附特性研究[J]. 食品工业科技,2022,43(8):76−83. [HUANG C D, AI S, LIU C Y, et al. Preparation and adsorption properties of chitosan/active claycomposite as sugar juice decolorization agent[J]. Science and Technology of Food Industry,2022,43(8):76−83. HUANG C D, AI S, LIU C Y, et al. Preparation and adsorption properties of chitosan/active claycomposite as sugar juice decolorization agent[J]. Science and Technology of Food Industry, 2022, 43(8): 76-83.
[10]	EL-MAHROUK G M, ABOUL-EINIEN M H, MAKHLOUF A I. Design, optimization, and evaluation of a novel metronidazole–loaded gastro–retentive pH–sensitive hydrogel[J]. Aaps Pharmscitech,2016,17(6):1285−1297. doi: 10.1208/s12249-015-0467-x
[11]	BERGER J, REIST M, MAYER J M, et al. Structure and interactions in covalently and ionically crosslinked chitosan hydrogel for biomedical applications[J]. European Journal of Pharmaceutics and Biopharmaceutics,2004,57:19−34. doi: 10.1016/S0939-6411(03)00161-9
[12]	杨上莹, 袁卉华, 易兵成. 柠檬酸改性壳聚糖水凝胶的制备与性能[J]. 功能高分子学报,2018,31(3):232−240. [YANG S Y, YUAN H H, YI B C. Fabrication and characterization of citric acid modified chitosan hydrogel[J]. Journal of Functional Polymers,2018,31(3):232−240. YANG S Y, YUAN H H, YI B C. Fabrication and characterization of citric acid modified chitosan hydrogel[J]. Journal of Functional Polymers, 2018, 31(3): 232–240.
[13]	YU R, ZHANG Y, BARBOIU M, et al. Biobased pH–responsive and self–healing hydrogels prepared from O–carboxymethyl chitosan and a 3–dimensional dunamer as cartilage engineering scaffold[J]. Carbohydrate Polymers,2020,244:116471. doi: 10.1016/j.carbpol.2020.116471
[14]	张立彦, 李作为, 黎梅兰, 等. 丙烯酸接枝壳聚糖水凝胶的制备及其pH敏感性[J]. 化工进展,2008,27(4):585−589. [ZHANG L Y, LI Z W, LI M L, et al. Preparation of N-carboxyethl chitosan hydrogel and its pH-sensitivity[J]. Chemical Industry and Engineering Progress,2008,27(4):585−589. ZHANG L Y, LI Z W, LI M L, et al. Preparation of N-carboxyethl chitosan hydrogel and its pH-sensitivity[J]. Chemical Industry and Engineering Progress, 2008, 27(4): 585-589.
[15]	PANDA J J, MISHRA A, BASU A, et al. Stimuli responsive self–assembled hydrogel of a low molecular weight free dipeptide with potential for tunable drug delivery[J]. Biomaromolecules,2008,9(8):2244−2250.
[16]	李平, 曾良鹏, 郭宏磊, 等. 两性离子水凝胶的研究进展[J]. 高分子学报,2020,51(12):1307−1320. [LI P, ZENG L P, GUO H L, et al. Research progress in zwitterionic hydrogels[J]. Acta Polymerica Sinica,2020,51(12):1307−1320. LI P, ZENG LP, GUO HL, et al. Research progress in zwitterionic hydrogels[J]. Acta Polymerica Sinica, 2020, 51(12): 1307-1320.
[17]	高翠英, 孟俊亮, 李彦威. 紫外分光光度法测定马来酸含量[J]. 太原理工大学学报,2008,39(3):230−231. [GAO C Y, MENG J L, LI Y W. Determination of the purity of maleic acid by UV spectrophotometry[J]. Journal of Taiyuan University of Technology,2008,39(3):230−231. GAO C Y, MENG J L, LI Y W. Determination of the purity of maleic acid by UV spectrophotometry[J]. Journal of Taiyuan University of Technology, 2008, 39(3): 230-231.
[18]	李英, 赵婉君, 叶霞, 等. 壳聚糖马来酸盐的制备及其膜性能[J]. 食品工业科技,2020,41(15):211−215. [LI Y, ZHAO W J, YE X, et al. Preparation of chitosan maleic salt and properties of its film[J]. Science and Technology of Food Industry,2020,41(15):211−215. LI Y, ZHAO W J, YE X, et al. Preparation of chitosan maleic salt and properties of its film[J]. Science and Technology of Food Industry, 2020, 41(15): 211-215.
[19]	LIU C X, DONG C F, LIU S H, et al. Multiple chiroptical switches and logic circuit based on salicyl- imine- chitosan hydrogel[J]. Carbohyd Polymers,2021,257:117534. doi: 10.1016/j.carbpol.2020.117534
[20]	李煦, 董翠芳, 刘长霞, 等. 负载花色苷的壳聚糖-水杨醛水凝胶的制备及性能[J]. 食品工业科技,2023,44(9):111−118. [LI X, DONG C F, LIU C X, et al. Preparation and properties of chitosan salicylaldehyde hydrogel loaded with anthocyanins[J]. Science and Technology of Food Industry,2023,44(9):111−118. LI X, DONG C F, LIU C X, et al. Preparation and properties of chitosan salicylaldehyde hydrogel loaded with anthocyanins[J]. Science and Technology of Food Industry, 2023, 44(9): 111–118.
[21]	ESTROFF L A, HAMILTO A D. Water gelation by small organic molecules[J]. Chemical Reviews,2004,104(3):1201−1217. doi: 10.1021/cr0302049
[22]	回瑞华, 关崇新, 侯冬岩. 羧酸及其盐红外光谱特性的研究[J]. 鞍山师范学院学报,2001,3(1):95−98. [HUI R H, GUAN C X, HOU D Y. Study on IR characteristics of carboxylic acid and their salts[J]. Journal of Anshan Normal University,2001,3(1):95−98. HUI R H, GUAN C X, HOU D Y. Study on IR characteristics of carboxylic acid and their salts[J]. Journal of Anshan Normal University, 2001, 3(1): 95-98.
[23]	叶霞, 刘长霞, 张泽平. 壳聚糖醋酸盐的制备及其油脂吸附性能研究[J]. 现代食品科技,2019,35(9):258−264. [YE X, LIU C X, ZHANG Z P. The preparation of chitosan acetate salt and its fat-binding capacity[J]. Modern Food Science & Technology,2019,35(9):258−264. YE X, LIU C X, ZHANG Z P. The preparation of chitosan acetate salt and its fat-binding capacity[J]. Modern Food Science & Technology, 2019, 35(9): 258–264.
[24]	林贤福. 现代波谱分析方法[M]. 上海: 华东理工大学出版社, 2009, 33 LIN X F. Modern spectral analysis methods[M]. Shanghai: East China University of Science and Technology Press, 2009, 33.
[25]	董翠芳, 王洪玲, 刘长霞, 等. pH响应的壳聚糖–糠醛水凝胶的构筑及自愈合性能[J]. 高分子材料科学与工程,2020,36(11):127−133. [DONG C F, WANG H L, LIU C X, et al. Fabrication of pH responsive chitosan–furfural hydrogel and its self-healing ability[J]. Polymeric Materials Science and Engineering,2020,36(11):127−133. DONG C F, WANG H L, LIU C X, et al. Fabrication of pH responsive chitosan–furfural hydrogel and its self-healing ability[J]. Polymeric Materials Science and Engineering, 2020, 36(11): 127–133.
[26]	GAROFF R A, LITZINGER E A, CONNOR R E, et al. Helical aggregation of cyanine dyes on DNA templates: effect of dye structure on formation of homo and hetero aggregates[J]. Langmuir,2002,18(16):6330−6337. doi: 10.1021/la025742f
[27]	李云龙, 林松柏, 肖春妹, 等. 高吸水树脂吸水机理的探讨[J]. 材料导报,2004,18(III):230−232. [LI Y L, LIN S B, XIAO C M, et al. Study on water absorbing mechanism of super absorbent resin[J]. Materials Reports,2004,18(III):230−232. LI Y L, LIN S B, XIAO C M, et al. Study on water absorbing mechanism of super absorbent resin[J]. Materials Reports, 2004, 18(III): 230–232.
[28]	ANTHONSEN M W, VARUM K M, SMIDSPOD O. Solution properties of chitosans: conformation and chain stiffness of chitosans with different degrees of N-acetylation[J]. Carbohydrate Polymers,1993,22(3):193−201. doi: 10.1016/0144-8617(93)90140-Y
[29]	RODRÍGUEZ R, ALVAREZ–LORENZO C, CONCHEIRO A. Cationic cellulose hydrogels: kinetics of the crosslinking process and characterization as pH/ion sensitive drug delivery systems[J]. Journal of Controlled Release,2003,86(2/3):253265.
[30]	CHEN S L, LIU M Z, JIN S P, et al. Preparation of ionic-crosslinked chitosan-based gel beads and effect of reaction conditions on drug release behaviors[J]. International Journal of Pharmaceutics,2008,349:180−187. doi: 10.1016/j.ijpharm.2007.08.029
[31]	ZHANG Y L, FU C K, LI Y S, et al. Synthesis of an injectable, self-healable and dual responsive hydrogel for drug delivery and 3D cell cultivation[J]. Polymer Chemistry,2017,8(3):537−544. doi: 10.1039/C6PY01704E
[32]	KARIMI A R, BAHAREH R, LEILA R, et al. Chitosan hydrogels cross–linked with tris (2-(2-formylphenoxy) ethyl) amine: swelling and drug delivery[J]. International Journal of Biological Macromolecules,2018,118:1863−1870. doi: 10.1016/j.ijbiomac.2018.07.037
[33]	BOONSONGRIT Y, MITREVEJ A, MUELLER B W. Chitosan drug binding by ionic interaction[J]. European Journal of Pharmaceutics and Biopharmaceutics,2006,62:267−274. doi: 10.1016/j.ejpb.2005.09.002

Supplements (0)

Cited By

Cited by

Periodical cited type(2)

1.	杨文萱，徐佳漫，郑君娜，徐梓烨，柯武康，李芬芬. 食源性多糖生物活性及其在食品加工中的应用研究进展. 食品安全导刊. 2025(11): 179-186 .
2.	徐景懿，辛嘉英，宋琪，贺姣，张卫丹. 酶催化酚酸改性及其在饲料领域的应用. 饲料工业. 2024(24): 138-144 .