journal article·2019-06

Self-healing alginate hydrogel based on dynamic acylhydrazone and multiple hydrogen bonds

Liyuan Qiao, Chengde Liu, Cheng Liu, Liquan Yang, Manxia Zhang, Wentao Liu, Jinyan Wang, Xigao Jian

Journal of Materials Science· Volume 54· Issue 11
Publisher page

Abstract

Dialdehyde-terminated PEG (PEG–CHO) and adipic dihydrazide-modified alginate (ALG-ADH) was developed to provide aldehyde and hydrazide active sites, respectively, and thus to obtain dynamic acylhydrazone bonds, which endow alginate hydrogel with excellent self-healing property. Different concentrations of cross-linking agent have been added, and their influence on the structure, morphology, mechanical properties and self-healing performance has been evaluated. The gelation kinetics, shear performance and compressive property have been investigated in detail. The hydrogel with 5% cross-linking agent exhibited the highest mechanical performance, with the shear modulus of 0.234 MPa and compressive modulus of 0.288 MPa. Due to dynamic acylhydrazone and multiple hydrogen bonds, the hydrogels have demonstrated excellent self-healing properties. After self-healing process, the hydrogel has retained 84.4% of the original tensile modulus. The as-prepared alginate hydrogel was molded into different shapes to exhibit the excellent plasticity. Moreover, when tetracycline hydrochloride was loaded into the hydrogel system as a model drug, the modified alginate hydrogel demonstrated the fastest drug release rate at pH = 7.4. It is suggested that the self-healing alginate hydrogel has a great potential in drug delivery, such as targeted drug release in intestinal treatment.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Hydrogels: synthesis, properties, applications · Advanced Drug Delivery Systems · Supramolecular Self-Assembly in Materials

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (57)

Show source-provided references
1. Taylor DL, Panhuis MIH (2016) Self-healing hydrogels. Adv Mater 28:9060–909310.1002/adma.201601613 ↗
2. Wu J, Han S, Yang T et al (2018) Highly stretchable and transparent thermistor based on self-healing double network hydrogel. ACS Appl Mater Interfaces 10:19097–1910510.1021/acsami.8b03524 ↗
3. Xiong C, Zhang L, Xie M, Sun R (2018) Photoregulating of stretchability and toughness of a self-healable polymer hydrogel. Macromol Rapid Commun 39(10):1800018. https://doi.org/10.1002/marc.20180001810.1002/marc.201800018 ↗
4. Utech S, Boccaccini AR (2016) A review of hydrogel-based composites for biomedical applications: enhancement of hydrogel properties by addition of rigid inorganic fillers. J Mater Sci 51:271–310. https://doi.org/10.1007/s10853-015-9382-510.1007/s10853-015-9382-5 ↗
5. Huang Q, Zou Y, Arno MC et al (2017) Hydrogel scaffolds for differentiation of adipose-derived stem cells. Chem Soc Rev 46:6255–627510.1039/C6CS00052E ↗
6. Zhou X, Guo B, Zhang L, Hu G-H (2017) Progress in bio-inspired sacrificial bonds in artificial polymeric materials. Chem Soc Rev 46:6301–632910.1039/C7CS00276A ↗
7. Tuncaboylu DC, Sari M, Oppermann W, Okay O (2011) Tough and self-healing hydrogels formed via hydrophobic interactions. Macromolecules 44:4997–500510.1021/ma200579v ↗
8. Chen Q, Zhu L, Chen H et al (2015) A novel design strategy for fully physically linked double network hydrogels with tough, fatigue resistant, and self-healing properties. Adv Funct Mater 25:1598–160710.1002/adfm.201404357 ↗
9. Chu CW, Ravoo BJ (2017) Hierarchical supramolecular hydrogels: self-assembly by peptides and photo-controlled release via host-guest interaction. Chem Commun 53:12450–1245310.1039/C7CC07859E ↗
10. Jia YG, Jin J, Liu S, Ren L, Luo J, Zhu XX (2018) Self-healing hydrogels of low molecular weight poly(vinyl alcohol) assembled by host-guest recognition. Biomacromol 19:626–63210.1021/acs.biomac.7b01707 ↗
11. Crupi V, Fontana A, Majolino D et al (2014) Hydrogen-bond dynamics of water confined in cyclodextrin nanosponges hydrogel. J Incl Phenom Macrocycl Chem 80:69–7510.1007/s10847-014-0387-5 ↗
12. Dai X, Zhang Y, Gao L et al (2015) A mechanically strong, highly stable, thermoplastic, and self-healable supramolecular polymer hydrogel. Adv Mater 27:3566–357110.1002/adma.201500534 ↗
13. Bastings MMC, Koudstaal S, Kieltyka RE et al (2014) A fast pH-switchable and self-healing supramolecular hydrogel carrier for guided, local catheter injection in the infarcted myocardium. Adv Healthc Mater 3:70–7810.1002/adhm.201300076 ↗
14. Jeon I, Cui J, Illeperuma WR, Aizenberg J, Vlassak JJ (2016) Extremely stretchable and fast self-healing hydrogels. Adv Mater 28:4678–468310.1002/adma.201600480 ↗
15. Mayr J, Saldias C, Diaz Diaz D (2018) Release of small bioactive molecules from physical gels. Chem Soc Rev 47:1484–151510.1039/C7CS00515F ↗
16. Yang X, Liu G, Peng L et al (2017) Highly efficient self-healable and dual responsive cellulose-based hydrogels for controlled release and 3D cell culture. Adv Funct Mater 27(40):1703174. https://doi.org/10.1002/adfm.20170317410.1002/adfm.201703174 ↗
17. Guo Z, Ma W, Gu H et al (2017) pH-Switchable and self-healable hydrogels based on ketone type acylhydrazone dynamic covalent bonds. Soft Matter 13:7371–738010.1039/C7SM00916J ↗
18. Yu F, Cao X, Du J, Wang G, Chen X (2015) Multifunctional hydrogel with good structure integrity, self-healing, and tissue-adhesive property formed by combining Diels-Alder click reaction and acylhydrazone bond. ACS Appl Mater Interfaces 7:24023–2403110.1021/acsami.5b06896 ↗
19. Tseng TC, Hsieh FY, Theato P, Wei Y, Hsu Sh (2017) Glucose-sensitive self-healing hydrogel as sacrificial materials to fabricate vascularized constructs. Biomaterials 133:20–2810.1016/j.biomaterials.2017.04.008 ↗
20. Guan Y, Zhang Y (2013) Boronic acid-containing hydrogels: synthesis and their applications. Chem Soc Rev 42:8106–812110.1039/c3cs60152h ↗
21. Kabb CP, O’Bryan CS, Deng CC, Angelini TE, Sumerlin BS (2018) Photoreversible covalent hydrogels for soft-matter additive manufacturing. ACS Appl Mater Interfaces 10:16793–1680110.1021/acsami.8b02441 ↗
22. Drury JL, Mooney DJ (2003) Hydrogels for tissue engineering: scaffold design variables and applications. Biomaterials 24:4337–435110.1016/S0142-9612(03)00340-5 ↗
23. Liu FG, Li RR, Mao LK, Gao YX (2018) Ethanol-induced composite hydrogel based on propylene glycol alginate and zein: formation, characterization and application. Food Chem 255:390–39810.1016/j.foodchem.2018.02.072 ↗
24. Mogosanu GD, Grumezescu AM (2014) Natural and synthetic polymers for wounds and burns dressing. Int J Pharm 463:127–13610.1016/j.ijpharm.2013.12.015 ↗
25. Pawar SN, Edgar KJ (2012) Alginate derivatization: a review of chemistry, properties and applications. Biomaterials 33:3279–330510.1016/j.biomaterials.2012.01.007 ↗
26. Chang D, Lei J, Cui H et al (2012) Disulfide cross-linked nanospheres from sodium alginate derivative for inflammatory bowel disease: preparation, characterization, and in vitro drug release behavior. Carbohyd Polym 88:663–66910.1016/j.carbpol.2012.01.020 ↗
27. Li G, Zhang G, Sun R, Wong C-P (2017) Mechanical strengthened alginate/polyacrylamide hydrogel crosslinked by barium and ferric dual ions. J Mater Sci 52:8538–8545. https://doi.org/10.1007/s10853-017-1066-x10.1007/s10853-017-1066-x ↗
28. Killion JA, Geever LM, Devine DM, Grehan L, Kennedy JE, Higginbotham CL (2012) Modulating the mechanical properties of photopolymerised polyethylene glycol–polypropylene glycol hydrogels for bone regeneration. J Mater Sci 47:6577–6585. https://doi.org/10.1007/s10853-012-6588-710.1007/s10853-012-6588-7 ↗
29. Chaudhuri O, Gu L, Klumpers D et al (2016) Hydrogels with tunable stress relaxation regulate stem cell fate and activity. Nat Mater 15:326–33610.1038/nmat4489 ↗
30. Zhu J (2010) Bioactive modification of poly(ethylene glycol) hydrogels for tissue engineering. Biomaterials 31:4639–465610.1016/j.biomaterials.2010.02.044 ↗
31. Vermonden T, Censi R, Hennink WE (2012) Hydrogels for protein delivery. Chem Rev 112:2853–288810.1021/cr200157d ↗
32. Slaughter BV, Khurshid SS, Fisher OZ, Khademhosseini A, Peppas NA (2009) Hydrogels in regenerative medicine. Adv Mater 21:3307–332910.1002/adma.200802106 ↗
33. Tang Q, Sun X, Li Q, Lin J, Wu J (2009) Preparation of porous polyacrylate/poly(ethylene glycol) interpenetrating network hydrogel and simplification of Flory theory. J Mater Sci 44:3712–3718. https://doi.org/10.1007/s10853-009-3496-610.1007/s10853-009-3496-6 ↗
34. Lee TT, Garcia JR, Paez JI et al (2015) Light-triggered in vivo activation of adhesive peptides regulates cell adhesion, inflammation and vascularization of biomaterials. Nat Mater 14:352–36010.1038/nmat4157 ↗
35. Schieber C, Bestetti A, Lim JP et al (2012) Conjugation of transferrin to azide-modified CdSe/ZnS core-shell quantum dots using Cyclooctyne click chemistry. Angew Chem Int Ed 51:10523–1052710.1002/anie.201202876 ↗
36. Gattásasfura KM, Stabler CL (2009) Chemoselective cross-linking and functionalization of alginate via Staudinger ligation. Biomacromol 10:3122–312910.1021/bm900789a ↗
37. Passemard S, Szabo L, Noverraz F et al (2017) Synthesis strategies to extend the variety of alginate-based hybrid hydrogels for cell microencapsulation. Biomacromol 18:2747–275510.1021/acs.biomac.7b00665 ↗
38. Zhang Y, Tao L, Li S, Wei Y (2011) Synthesis of multiresponsive and dynamic chitosan-based hydrogels for controlled release of bioactive molecules. Biomacromol 12:2894–290110.1021/bm200423f ↗
39. Wang X, Chang L, Hu J et al (2017) Self-healable hydrogels with crosslinking induced thermo-responsiveness and regulated properties from water soluble polymer. Polymer 131:202–20810.1016/j.polymer.2017.10.046 ↗
40. Chang R, An H, Li X et al (2017) Self-healable polymer gels with multi-responsiveness of gel-sol-gel transition and degradability. Polym Chem 8:1263–127110.1039/C6PY02122K ↗
41. Wang X, Bian G, Zhang M et al (2017) Self-healable hydrogels with cross-linking induced thermo-responsiveness and multi-triggered gel-sol-gel transition. Polym Chem 8:2872–288010.1039/C7PY00445A ↗
42. Gao C, Liu M, Chen J, Zhang X (2009) Preparation and controlled degradation of oxidized sodium alginate hydrogel. Polym Degrad Stab 94:1405–141010.1016/j.polymdegradstab.2009.05.011 ↗
43. Tan H, Ramirez CM, Miljkovic N, Li H, Rubin JP, Marra KG (2009) Thermosensitive injectable hyaluronic acid hydrogel for adipose tissue engineering. Biomaterials 30:6844–685310.1016/j.biomaterials.2009.08.058 ↗
44. Yeo Y, Highley CB, Bellas E et al (2006) In situ cross-linkable hyaluronic acid hydrogels prevent post-operative abdominal adhesions in a rabbit model. Biomaterials 27:4698–470510.1016/j.biomaterials.2006.04.043 ↗
45. Ito T, Yeo Y, Highley CB, Bellas E, Benitez CA, Kohane DS (2007) The prevention of peritoneal adhesions by in situ cross-linking hydrogels of hyaluronic acid and cellulose derivatives. Biomaterials 28:975–98310.1016/j.biomaterials.2006.10.021 ↗
46. Jia X, Colombo G, Padera R, Langer R, Kohane DS (2004) Prolongation of sciatic nerve blockade by in situ cross-linked hyaluronic acid. Biomaterials 25:4797–480410.1016/j.biomaterials.2003.12.012 ↗
47. Maciel D, Figueira P, Xiao S et al (2013) Redox-responsive alginate nanogels with enhanced anticancer cytotoxicity. Biomacromol 14:3140–314610.1021/bm400768m ↗
48. Dankers PYW, Hermans TM, Baughman TW et al (2012) Hierarchical formation of supramolecular transient networks in water: a modular injectable delivery system. Adv Mater 24:2703–270910.1002/adma.201104072 ↗
49. Jeon O, Bouhadir KH, Mansour JM, Alsberg E (2009) Photocrosslinked alginate hydrogels with tunable biodegradation rates and mechanical properties. Biomaterials 30:2724–273410.1016/j.biomaterials.2009.01.034 ↗
50. Wei Z, Yang JH, Liu ZQ et al (2015) Novel Biocompatible Polysaccharide-Based Self-Healing Hydrogel. Adv Funct Mater 25:1352–135910.1002/adfm.201401502 ↗
51. Liu B, Wang Y, Miao Y et al (2018) Hydrogen bonds autonomously powered gelatin methacrylate hydrogels with super-elasticity, self-heal and underwater self-adhesion for sutureless skin and stomach surgery and E-skin. Biomaterials 171:83–9610.1016/j.biomaterials.2018.04.023 ↗
52. Lin Q, Jiang X-M, Liu L et al (2017) A novel supramolecular organogel based on acylhydrazone functionalized pillar 5 arene acts as an I- responsive smart material. Soft Matter 13:7222–722610.1039/C7SM01576C ↗
53. Ye X, Li X, Shen Y, Chang G, Yang J, Gu Z (2017) Self-healing pH-sensitive cytosine- and guanosine-modified hyaluronic acid hydrogels via hydrogen bonding. Polymer 108:348–36010.1016/j.polymer.2016.11.063 ↗
54. Haring M, Rodriguez-Lopez J, Grijalvo S et al (2018) Isosteric substitution of 4H-1,2,4-triazole by 1H-1,2,3-triazole in isophthalic derivative enabled hydrogel formation for controlled drug delivery. Mol Pharm 15:2963–297210.1021/acs.molpharmaceut.7b01049 ↗
55. Kim C-K, Lee E-J (1992) The controlled release of blue dextran from alginate beads. Int J Pharm 79:11–1910.1016/0378-5173(92)90088-J ↗
56. Wells LA, Sheardown H (2007) Extended release of high pI proteins from alginate microspheres via a novel encapsulation technique. Eur J Pharm Biopharm 65:329–33510.1016/j.ejpb.2006.10.018 ↗
57. Xu Y, Zhan C, Fan L, Wang L, Zheng H (2007) Preparation of dual crosslinked alginate–chitosan blend gel beads and in vitro controlled release in oral site-specific drug delivery system. Int J Pharm 336:329–33710.1016/j.ijpharm.2006.12.019 ↗