儿茶酚-天然大分子-金属离子水凝胶的研究进展

doi:10.19677/j.issn.1004-7964.2019.06.006

皮革科学与工程 ›› 2019, Vol. 29 ›› Issue (06): 30-37.doi: 10.19677/j.issn.1004-7964.2019.06.006

儿茶酚-天然大分子-金属离子水凝胶的研究进展

石楚桐^1,2*, 宋彬^1,2*, 辜海彬^1,2*

1.皮革化学与工程教育部重点实验室(四川大学),四川成都 610065;
2.制革清洁技术国家工程实验室(四川大学),四川成都 610065

收稿日期:2019-05-29 出版日期:2019-12-28 上线日期:2020-03-27
作者简介:石楚桐(1999-),女,四川大学轻化工程专业2017级本科生,E-mail:sct0312@foxmail.com。
基金资助:
四川省国际科技合作与交流研究计划项目(2018HH0038);四川大学大学生创新训练计划项目(C2019104671)

Research Progress on the Catechol-modified Biomacromolecular Hydrogels Crosslinked by Coordination with Metal Ions

SHI Chutong^1,2*, SONG Bin^1,2*, GU Haibin^1,2*

1. Key Laboratory of Leather Chemistry and Engineering of Ministry of Education, Sichuan University, Chengdu 610065, China;
2. National Engineering Laboratory for Clean Technology of Leather Manufacture, Sichuan University, Chengdu 610065, China

Received:2019-05-29 Online:2019-12-28 Published:2020-03-27

摘要/Abstract

摘要： 受贻贝可以在潮湿环境中牢固粘附于介质表面现象的启发,研究者们在明确了儿茶酚基团在贻贝黏附过程中的重要作用之后,据此开发出多种仿贻贝的儿茶酚基功能材料。本文主要介绍了近年来利用儿茶酚结构对壳聚糖、透明质酸、海藻酸盐、蛋白质、多肽、明胶等天然生物大分子进行接枝改性,进而通过与金属离子的配位交联作用,开发多功能水凝胶的研究进展。

关键词: 儿茶酚, 多巴胺, 生物大分子, 配位交联, 水凝胶

Abstract: Inspired by the phenomenon that mussels can adhere firmly to the surface of media in the wet environment, researchers have identified the important role of catechol groups in the adhesion process of mussels. Thus, scientists have developed a variety of mussel-like catechol-modified hydrogel functional materials. Herein, this review summarizes the most recent progress in the fabrication of catechol-modified multifunctional biomacromolecule hydrogels crosslinked by coordination with metal ions, and the discussed biomacromolecules involve chitosan, hyaluronic acid, alginate, protein, polypeptide and gelatin. Focus is on the modification of biomacromolecules by catechol groups, fabrication method, gelling mechanism, multifunctionality and potential application of these hydrogels.

Key words: catechol, dopamine, biomacromolecule, coordination crosslinking, hydrogels

中图分类号:

TS512

石楚桐, 宋彬, 辜海彬. 儿茶酚-天然大分子-金属离子水凝胶的研究进展[J]. 皮革科学与工程, 2019, 29(06): 30-37.

SHI Chutong, SONG Bin, GU Haibin. Research Progress on the Catechol-modified Biomacromolecular Hydrogels Crosslinked by Coordination with Metal Ions[J]. Leather Science and Engineering, 2019, 29(06): 30-37.

参考文献

[1] 刘瑞雪,周腾,樊晓敏,等.明胶基复合水凝胶研究进展[J].轻工学报,2018,33(06):42-54+81.
[2] Forooshani P K, Lee B P.Recent approaches in designing bioadhesive materials inspired by mussel adhesive protein[J]. Journal of Polymer Science Part A-Polymer Chemistry, 2017, 55(1): 9-33.
[3] Guo Z W, Ni K F, Wei D Z, et al.Fe3+-induced oxidation and coordination cross-linking in catechol-chitosan hydrogels under acidic pH conditions[J]. RSC Advances, 2015, 5(47): 37377-37384.
[4] Li S B, Wang L, Yu X M, et al.Synthesis and characterization of a novel double cross-linked hydrogel based on Diels-Alder click reaction and coordination bonding[J]. Materials Science & Engineering C-Materials for Biological Applications, 2018, 82:299-309.
[5] Yavvari P S, Srivastava A.Robust, self-healing hydrogels synthesised from catechol rich polymers[J]. Journal of Materials Chemistry B, 2015, 3(5): 899-910.
[6] Yavvari P S, Pal S, Kumar S, et al.Injectable, Self-Healing Chimeric Catechol-Fe(III) Hydrogel for Localized Combination Cancer Therapy[J]. ACS Biomaterials Science & Engineering, 2017, 3(12): 3404-3413.
[7] Chen N, Qin L M, Pan Q M.Mussel-inspired healing of a strong and stiff polymer[J]. Journal of Materials Chemistry A, 2018, 6(15): 6667-6674.
[8] Chen N, Pan Q M.Mussel-Inspired Self-Healing of Ultralight Magnetic Frameworks[J]. ACS Sustainable Chemistry & Engineering, 2017, 5(9): 7905-7911.
[9] Azevedo S, Costa A M S, Andersen A, et al. Bioinspired Ultratough Hydrogel with Fast Recovery, Self-Healing, Injectability and Cytocompatibility[J]. Advanced Materials, 2017, 29(28): 1700759.
[10] 王莉,汪刘建,吉亚丽.儿茶酚基团改性壳聚糖组织胶黏剂的制备和表征[J].功能高分子学报,2017,30(1):59-66.
[11] Zeng Z W, Mo X M.Rapid in situ cross-linking of hydrogel adhesives based on thiol-grafted bio-inspired catechol-conjugated chitosan[J]. Journal of Biomaterials Applications, 2017, 32(5): 612-621.
[12] Ghadban A, Ahmed A S, Ping Y, et al.Bioinspired pH and magnetic responsive catechol-functionalized chitosan hydrogels with tunable elastic properties[J]. Chemical Communications, 2016, 52(4): 697-700.
[13] Ryu J H, Lee Y, Kong W H, et al.Catechol-Functionalized Chitosan/Pluronic Hydrogels for Tissue Adhesives and Hemostatic Materials[J]. Biomacromolecules, 2011, 12(7):2653-2659.
[14] Kim K, Ryu J H, Lee D Y, et al.Bio-inspired catechol conjugation converts water-insoluble chitosan into a highly water-soluble, adhesive chitosan derivative for hydrogels and LbL assembly[J]. Biomaterials Science 2013, 1(7): 783-790.
[15] Zhang J M, Tao X Y, Liu J W, et al.Fe3+-induced bioinspired chitosan hydrogels for the sustained and controlled release of doxorubicin[J]. RSC Advances, 2016, 6(53): 47940-47947.
[16] Shin J, Lee J S, Lee C, et al.Tissue Adhesive Catechol-Modified Hyaluronic Acid Hydrogel for Effective, Minimally Invasive Cell Therapy[J]. Advanced Functional Materials, 2015, 25(25): 3814-3824.
[17] Xu X, Jha A K, Harrington D A, et al.Hyaluronic acid-based hydrogels: from a natural polysaccharide to complex networks[J]. Soft Matter 2012, 8(12): 3280-3294.
[18] Lee Y, Chung H J, Yeo S, et al.Thermo-sensitive, injectable, and tissue adhesive sol-gel transition hyaluronic acid/pluronic composite hydrogels prepared from bio-inspired catechol-thiol reaction[J]. Soft Matter 2010, 6(5): 977-983.
[19] Hong S, Yang K, Kang B, et al.Hyaluronic Acid Catechol: A Biopolymer Exhibiting a pH-Dependent Adhesive or Cohesive Property for Human Neural Stem Cell Engineering[J]. Advanced Functional Materials, 2013, 23(14): 1774-1780.
[20] Shin J, Lee J S, Lee C, et al.Tissue Adhesive Catechol-Modified Hyaluronic Acid Hydrogel for Effective, Minimally Invasive Cell Therapy[J]. Advanced Functional Materials, 2015, 25(25): 3814-3824.
[21] Park H J, Jin Y, Shin J, et al.Catechol-Functionalized Hyaluronic Acid Hydrogels Enhance Angiogenesis and Osteogenesis of Human Adipose-Derived Stem Cells in Critical Tissue Defects[J]. Biomacromolecules, 2016, 17(6): 1939-1948.
[22] Zhang Z, Gao Z L, Wang Y T, Eco-Friendly, Self-Healing Hydrogels for Adhesive and Elastic Strain Sensors, Circuit Repairing, and Flexible Electronic Devices, Macromolecules, 2019, 52(6): 2531-2541.
[23] Lee J, Chang K, Kim S, et al.Phase Controllable Hyaluronic Acid Hydrogel with Iron(III) Ion–Catechol Induced Dual Cross-Linking by Utilizing the Gap of Gelation Kinetics[J]. Macromolecules, 2016, 49(19): 7450-7459.
[24] Guo Z W, Mi S L, Sun W.A Facile Strategy for Preparing Tough, Self-Healing Double-Network Hyaluronic Acid Hydrogels Inspired by Mussel Cuticles[J]. Macromolecular Materials and Engineering, 2019, 304(4): 1800715.
[25] Guo Z W, Mi S L, Sun W.The multifaceted nature of catechol chemistry: bioinspired pH-initiated hyaluronic acid hydrogels with tunable cohesive and adhesive properties[J]. Journal of Materials Chemistry B, 2018, 6(39): 6234-6244.
[26] 王清华,钟文菲,何盟.藻酸盐敷料的临床应用:与传统材料特征的比较[J].中国组织工程研究与临床康复,2010,14(03):533-536.
[27] Gombotz W R, Wee S F.Protein release from alginate matrices[J]. Advanced Drug Delivery Reviews, 2012, 64: 194-205.
[28] Lee C, Shin J, Lee J S, et al.Bioinspired, Calcium-Free Alginate Hydrogels with Tunable Physical and Mechanical Properties and Improved Biocompatibility[J]. Biomacromolecules, 2013, 14(6): 2004-2013.
[29] Hou J X, Li C, Guan Y, et al.Enzymatically crosslinked alginate hydrogels with improved adhesion properties[J]. Polymer Chemistry, 2015, 6(12): 2204-2213.
[30] Kim S, Moon J M, Choi J S, et al.Mussel-Inspired Approach to Constructing Robust Multilayered Alginate Films for Antibacterial Applications[J]. Advanced Functional Materials, 2016, 26(23): 4099-4105.
[31] Hong S H, Shin M, Lee J, et al.STAPLE: Stable Alginate Gel Prepared by Linkage Exchange from Ionic to Covalent Bonds[J]. Advanced Healthcare Materials, 2016, 5(1): 75-79.
[32] Lee Y K, Lee S Y.A colorimetric alginate-catechol hydrogel suitable as a spreadable pH indicator[J]. Dyes and Pigments, 2014, 108: 1-6.
[33] Cholewinski A, Yang F K, Zhao B X.Underwater Contact Behavior of Alginate and Catechol-Conjugated Alginate Hydrogel Beads[J]. Langmuir, 2017, 33(34): 8353-8361.
[34] Tao F, Qin L M, Wang Z K, et al.Self-Healable and Cold-Resistant Supercapacitor Based on a Multifunctional Hydrogel Electrolyte[J]. ACS Applied Materials & Interfaces, 2017, 9(18): 15541-15548.
[35] Alegre-Requena J V, Häring M, Herrera R P, et al. Regulatory parameters of self-healing alginate hydrogel networks prepared via mussel-inspired dynamic chemistry[J]. New Journal of Chemistry, 2016, 40(10): 8493-8501.
[36] Zhu W Z, Peck Y, Iqbal J, et al.A novel DOPA-albumin based tissue adhesive for internal medical applications[J]. Biomaterials, 2017, 147: 99-115.
[37] Duan L, Yuan Q J, Xiang H Z, et al.Fabrication and characterization of a novel collagen-catechol hydrogel[J]. Journal of Biomaterials Applications, 2018, 32(7): 862-870.
[38] Kim B J, Oh D X, Kim S, et al.Mussel-Mimetic Protein-Based Adhesive Hydrogel[J]. Biomacromolecules, 2014, 15(5):1579-1585.
[39] Yang B, Lim C, Hwang D, et al.Switch of Surface Adhesion to Cohesion by Dopa-Fe³⁺ Complexation, in Response to Microenvironment at the Mussel Plaque/Substrate Interface[J]. Journal of Physical Chemistry B, 2016, 120(29):7265-7274.
[40] Thi P L, Lee Y, Thi T T H, et al. Catechol-rich gelatin hydrogels in situ hybridizations with silver nanoparticle for enhanced antibacterial activity[J]. Materials Science & Engineering C-Materials for Biological Applications, 2018, 92: 52-60.
[41] Cheng H, Yue K, Kazemzadeh-Narbat M, et al.Mussel-Inspired Multifunctional Hydrogel Coating for Prevention of Infections and Enhanced Osteogenesis[J]. ACS Applied Materials & Interfaces, 2017, 9(13): 11428-11439.
[42] Hong S, Pirovich D, Kilcoyne A, et al.Supramolecular Metallo-Bioadhesive for Minimally Invasive Use[J]. Advanced Materials, 2016, 28(39): 8675-8680.
[43] Kim J Y, Ryu S B, Park K D.Preparation and characterization of dual-crosslinked gelatin hydrogel via Dopa-Fe3+ complexation and fenton reaction[J]. Journal of Industrial and Engineering Chemistry, 2018, 58: 105-112.
[44] Zhu W Z, Yang J, Iqbal J, et al.A mussel-inspired double-crosslinked tissue adhesive on rat mastectomy model: seroma prevention and in vivo biocompatibility[J]. Journal of Surgical Research, 2017, 215: 173-182.
[45] Fan C J, Fu J Y, Zhu W Z, et al.A mussel-inspired double-crosslinked tissue adhesive intended for internal medical use[J]. Acta Biomaterialia, 2016, 33: 51-63.
[46] Choi Y C, Choi J S, Jung Y J, et al.Human gelatin tissue-adhesive hydrogels prepared by enzyme-mediated biosynthesis of DOPA and Fe³⁺ion crosslinking[J]. Journal of Materials Chemistry B, 2014, 2(2): 201-209.
[47] Liu Z, Yao P.Injectable shear-thinning xanthan gum hydrogel reinforced by mussel-inspired secondary crosslinking[J]. RSC Advances, 2015, 5(125): 103292-103301.

儿茶酚-天然大分子-金属离子水凝胶的研究进展

Research Progress on the Catechol-modified Biomacromolecular Hydrogels Crosslinked by Coordination with Metal Ions

PDF

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 11

编辑推荐

Metrics

本文评价

[1]	周建华, 晏亚飞, 周梦园. MXene@聚多巴胺的制备、性能和应用[J]. 皮革科学与工程, 2024, 34(1): 18-23.
[2]	乐薇, 张旭, 秦子波, 余小月, 熊善柏, 胡杨. 不同结构的多酚交联对胶原水凝胶理化性质的影响[J]. 皮革科学与工程, 2023, 33(5): 1-7.
[3]	石佳博, 张睿祯, 盛理, 刘强. 生物大分子基纳米复合功能膜的制备及应用研究进展[J]. 皮革科学与工程, 2023, 33(3): 24-30.
[4]	白龙, 金勇, 商翔, 林芯颖, 周荣. 胶原基离子水凝胶的制备及其在传感领域的应用研究[J]. 皮革科学与工程, 2022, 32(5): 1-5.
[5]	程玉林, 李国英. 衣康酸酐改性胶原制备光固化水凝胶[J]. 皮革科学与工程, 2022, 32(4): 14-19.
[6]	孙莉, 肖远航, 王春华, 穆畅道, 林炜. 利用制革废弃牛毛制备角蛋白基水凝胶研究[J]. 皮革科学与工程, 2022, 32(3): 6-12.
[7]	陆曼玲, 李阳, 麻寿江, 闫新秀, 刘军, 丁克毅, 陈华林. 基于氢键作用的自修复聚丙烯酸酯乳液的合成及性能[J]. 皮革科学与工程, 2022, 32(3): 59-64.
[8]	石楚桐, 宋彬, 辜海彬. 连苯三酚改性的天然大分子和单宁酸配位交联水凝胶的研究进展[J]. 皮革科学与工程, 2020, 30(1): 27-32.
[9]	潘界舟;宋寒冰;王盛华;金勇;. 聚丙烯酸-羧甲基壳聚糖水凝胶对皮革废水中Cr(Ⅲ)吸附研究[J]. , 2019, 29(03): 12-.
[10]	胡杰;宋玉奎;柴玉叶;兰云军;. 水性聚氨酯丙烯酸酯接枝角蛋白水凝胶的合成及性能[J]. , 2015, 25(03): 47-51.
[11]	张倩;穆畅道;李丽英;丁宗雷;林炜;. 原花青素诱导明胶水凝胶的形成与稳定[J]. , 2008, 18(03): 20-25.