An injectable and biodegradable hydrogel based on poly(α,β- aspartic acid) derivatives for localized drug delivery

Journal of Biomedical Materials Research - Part A

Volumn 102, Issue 3, 2014, Pages 628-638

  Lu, Caicai ^a   Wang, Xiaojuan ^a   Wu, Guolin ^a   Wang, Jingjing ^a   Wang, Yinong ^a   Gao, Hui ^b   Ma, Jianbiao ^b  

^a NANKAI UNIVERSITY   (China)

^b TIANJIN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

biodegradation; drug delivery; hydrazone; injectable hydrogel; poly(aspartic acid)

Indexed keywords

AMINOLYSIS REACTION; BIODEGRADABLE HYDROGELS; HYDRAZONES; INJECTABLE HYDROGELS; POLYASPARTIC ACID; POLYMERIC HYDROGELS; THERMAL POLYCONDENSATION; THREE-DIMENSIONAL STRUCTURE;

ALDEHYDES; AMINO ACIDS; BIOCOMPATIBILITY; BIODEGRADATION; CELL ADHESION; DRUG DELIVERY; INFRARED SPECTROSCOPY; SCANNING ELECTRON MICROSCOPY;

HYDROGELS;

ALDEHYDE; ASPARTIC ACID; DOXORUBICIN; HYDRAZINE; HYDRAZONE DERIVATIVE; POLYASPARTIC ACID; POLYMER;

AMINOLYSIS; ARTICLE; BIOCOMPATIBILITY; CATALYST; CELL ADHESION; CELL GROWTH; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CROSS LINKING; DEGRADATION KINETICS; DRUG DELIVERY SYSTEM; FOURIER TRANSFORM MASS SPECTROMETRY; GEL; HYDROGEL; IN VITRO STUDY; MORPHOLOGY; PH; POLYCONDENSATION; SCANNING ELECTRON MICROSCOPE;

BIODEGRADATION; DRUG DELIVERY; HYDRAZONE; INJECTABLE HYDROGEL; POLY(ASPARTIC ACID);

ANTIBIOTICS, ANTINEOPLASTIC; ASPARTIC ACID; BIOCOMPATIBLE MATERIALS; BIOPOLYMERS; DELAYED-ACTION PREPARATIONS; DOXORUBICIN; HYDRAZONES; HYDROGELS; HYDROGEN-ION CONCENTRATION; INJECTIONS; POROSITY;

EID: 84892622359     PISSN: 15493296     EISSN: 15524965     Source Type: Journal    
DOI: 10.1002/jbm.a.34725     Document Type: Article

References (56)

1. Hoffman AS,. Hydrogels for biomedical applications. Ann NY Acad Sci 2001; 944: 62-73.
2. Bhattarai N, Gunn J, Zhang M,. Chitosan-based hydrogels for controlled, localized drug delivery. Adv Drug Deliv Rev 2010; 62: 83-99.
3. Amin S, Rajabnezhad S, Kohli K,. Hydrogels as potential drug delivery systems. Sci Res Essays 2009; 3: 1175-1183.
4. Park HP, Park K,. Biocompatibility issues of implantable drug delivery systems. Pharm Res 1996; 13: 1770 - 1776.
5. Wichterle O, Lim D,. Hydrophilic gels for biological use. Nature 1960; 185: 117-118.
6. Nguyen MK, Lee DS,. Injectable biodegradable hydrogels. Macromol Biosci 2010; 10: 563-579.
7. Delair T,. In situ forming polysaccharide-based 3D-hydrogels for cell delivery in regenerative medicine. Carbohydr Polym 2012; 87: 1013-1019.
8. Li YL, Rodrigues J, Tomas H,. Injectable and biodegradable hydrogels: Gelation, biodegradation and biomedical applications. Chem Soc Rev 2012; 41: 2193-2221.
9. Huynh CT, Nguyen MK, Lee DS,. Injectable block copolymer hydrogels: Achievements and future challenges for biomedical applications. Macromolecules 2011; 44: 6629-6636.
10. Zhao L, Zhu L, Liu F, Liu C, Shan D, Wang Q, Zhang C, Li J, Liu J, Qu X, Yang Z. pH triggered injectable amphiphilic hydrogel containing doxorubicin and paclitaxel. Int J Pharm 2011; 410: 83-91.
11. Chang G, Yu L, Yang Z, Ding J,. A delicate ionizable-group effect on self-assembly and thermogelling of amphiphilic block copolymers in water. Polymer 2009; 50: 6111-6120.
12. Khutoryanskaya OV, Mayeva ZA, Mun GA, Khutoryanskiy VV,. Designing temperature-responsive biocompatible copolymers and hydrogels based on 2-hydroxyethyl(meth)acrylates. Biomacromolecules 2008; 9: 3353-3361.
13. Chiu YL, Chen SC, Su CJ, Hsiao CW, Chen YM, Chen HL, Sung HW,. pH-triggered injectable hydrogels prepared from aqueous N-palmitoyl chitosan: In vitro characteristics and in vivo biocompatibility. Biomaterials 2009; 30: 4877-4888.
14. Ding C, Zhao L, Liu F, Jun Cheng, Jingxia Gu S-D, Liu C, Qu X, Yang Z,. Dually responsive injectable hydrogel prepared by in situ cross-linking of glycol chitosan and benzaldehyde-capped PEO-PPO-PEO. Biomacromolecules 2010; 11: 1043-1051.
15. Tan H, Chu CR, Payne KA, Marra KG,. Injectable in situ forming biodegradable chitosan-hyaluronic acid based hydrogels for cartilage tissue engineering. Biomaterials 2009; 30: 2499-2506.
16. Weng L, Romanov A, Rooney J, Chen W,. Non-cytotoxic, in situ gelable hydrogels composed of N-carboxyethyl chitosan and oxidized dextran. Biomaterials 2008; 29: 3905-3913.
17. Nishi KK, Jayakrishnan A,. Self-gelling primaquine-gum arabic conjugate an injectable controlled delivery system for primaquine. Biomacromolecules 2007; 8: 84-90.
18. Zhang R, Huang Z, Xue M, Yang J, Tan T,. Detailed characterization of an injectable hyaluronic acid-polyaspartylhydrazide hydrogel for protein delivery. Carbohydr Polym 2011; 85: 717-725.
19. Pawar SN, Edgar KJ,. Alginate derivatization: A review of chemistry, properties and applications. Biomaterials 2012; 33: 3279-3305.
20. Xu X, Jha AK, Harrington DA, Farach-Carson MC, Jia XQ,. Hyaluronic acid-based hydrogels: From a natural polysaccharide to complex networks. Soft Matter 2012; 8: 3280-3294.
21. Berger J, Reist M, Mayer JM, Felt O, Peppas NA, Gurny R,. Structure and interactions in covalently and ionically crosslinked chitosan hydrogels for biomedical applications. Eur J Pharm Biopharm 2004; 57: 19-34.
22. Berger J, Reist M, Mayer JM, Felt O, Gurny R,. Structure and interactions in chitosan hydrogels formed by complexation or aggregation for biomedical applications. Eur J Pharm Biopharm 2004; 57: 35-52.
23. Vicente Gonzalez-Aramundiz J, Victoria Lozano M, Sousa-Herves A, Fernandez-Megia E, Csaba N,. Polypeptides and polyaminoacids in drug delivery. Expert Opin Drug Deliv 2012; 9: 183-201.
24. Osada K, Christie RJ, Kataoka K,. Polymeric micelles from poly(ethylene glycol)-poly(amino acid) block copolymer for drug and gene delivery. J R Soc Interface 2009; 6: 325-339.
25. Ren T-B, Xia W-J, Dong H-Q, Li Y-Y,. Sheddable micelles based on disulfide-linked hybrid PEG-polypeptide copolymer for intracellular drug delivery. Polymer 2011; 52: 3580-3586.
26. Obst M, Steinbuchel A,. Microbial degradation of poly(amino acid)s. Biomacromolecules 2004; 5: 1166-1176.
27. Wang Y, Wu G, Fan Y, Ma J,. pH-responsive self-assembly and conformational transition of partially propyl-esterified poly(alpha,beta- l -aspartic acid) as amphiphilic biodegradable polyanion. Colloids Surf B Biointerfaces 2009; 68: 13-19.
28. Moon JR, Kim MW, Kim D, Jeong JH, Kim J-H,. Synthesis and self-assembly behavior of novel polyaspartamide derivatives for anti-tumor drug delivery. Colloid Polym Sci 2011; 289: 63-71.
29. Seo K, Kim D,. pH-dependent hemolysis of biocompatible imidazole-grafted polyaspartamide derivatives. Acta Biomater 2010; 6: 2157-2164.
30. Lin W, Kim D,. pH-Sensitive micelles with cross-linked cores formed from polyaspartamide derivatives for drug delivery. Langmuir 2011; 27: 12090-12097.
31. Yang H-M, Park CW, Woo M-A, Kim MI, Jo YM, Park HG, Kim J-D,. HER2/neu antibody conjugated poly(amino acid)-coated iron oxide nanoparticles for breast cancer MR imaging. Biomacromolecules 2010; 11: 2866-2872.
32. Wang X, Wu G, Lu C, Zhao W, Wang Y, Fan Y, Gao H, Ma J,. A novel delivery system of doxorubicin with high load and pH-responsive release from the nanoparticles of poly (alpha,beta-aspartic acid) derivative. Eur J Pharm Sci 2012; 47: 256-264.
33. Akinori N, Hiroaki T, Ajioka M, Yamaguchi A,. Superabsorbent Polymer and Process for Producing Same. U.S Patent 5,461,085. 1995.
34. Gyenes T, Torma V, Zrínyi M,. Swelling properties of aspartic acid-based hydrogels. Colloids Surf A Physicochem Eng Aspects 2008; 319: 154-158.
35. Torma V, Gyenes T, Szakacs Z, Zrinyi M,. A novel potentiometric method for the determination of real crosslinking ratio of poly(aspartic acid) gels. Acta Biomater 2010; 6: 1186-1190.
36. Yoon SW, Chung DJ, Kim JH,. Preparation and swelling behavior of biodegradable hydrogels based on alpha,beta-poly(N-2-hydroxyethyl- d, l -aspartamide). J Appl Polym Sci 2003; 90: 3741-3746.
37. Kim JH, Lee JH, Yoon SW,. Preparation and swelling behavior of biodegradable superabsorbent gels based on polyaspartic acid. J Ind Eng Chem 2002; 8: 138-142.
38. Min SK, Kim SH, Kim JH,. Preparation and swelling behavior of biodegradable poly(aspartic acid)-based hydrogel. J Ind Eng Chem 2000; 6: 276-279.
39. Yang J, Wang F, Tan TW,. Degradation behavior of hydrogel based on cross linked poly(aspartic acid). J Appl Polym Sci 2010; 117: 178-185.
40. Pitarresi G, Palumbo FS, Cavallaro G, Fare S, Giammona G,. Scaffolds based on hyaluronan crosslinked with a polyaminoacid: Novel candidates for tissue engineering application. J Biomed Mater Res 2008; 87: 770-779.
41. Pitarresi G, Palumbo FS, Tripodo G, Cavallaro G, Giammona G,. Preparation and characterization of new hydrogels based on hyaluronic acid and α,β-polyaspartylhydrazide. Eur Polym J 2007; 43: 3953-3962.
42. Bae Y, Kataoka K,. Intelligent polymeric micelles from functional poly(ethylene glycol)-poly(amino acid) block copolymers. Adv Drug Deliv Rev 2009; 61: 768-784.
43. Zhou L, Cheng R, Tao H, Ma S, Guo W, Meng F, Liu H, Liu Z, Zhong Z,. Endosomal pH-activatable poly(ethylene oxide)-graft-doxorubicin prodrugs: Synthesis, drug release, and biodistribution in tumor-bearing mice. Biomacromolecules 2011; 12: 1460-1467.
44. Wang X, Wu G, Lu C, Wang Y, Fan Y, Gao H, Ma J,. Synthesis of a novel zwitterionic biodegradable poly (α,β-l-aspartic acid) derivative with some l-histidine side-residues and its resistance to non-specific protein adsorption. Colloids Surf B Biointerfaces 2011; 86: 237-241.
45. Thombre SM, Sarwade BD,. Synthesis and biodegradability of polyaspartic acid: A critical review. J Macromol Sci Pure 2005; 42: 1299-1315.
46. Licciardi M, Cavallaro G, Di Stefano M, Pitarresi G, Fiorica C, Giammona G,. New self-assembling polyaspartylhydrazide copolymer micelles for anticancer drug delivery. Int J Pharm 2010; 396: 219-228.
47. Neri P, Antoni G, Benvenuti F, Cocola F, Gazzei aG,. Synthesis of alpha, beta-poly [(2-hydroxyethyl)- dl -aspartamide], a new plasma expander. J Med Chem 1973; 16: 893-897.
48. Lee F, Chung JE, Kurisawa M,. An injectable enzymatically crosslinked hyaluronic acid-tyramine hydrogel system with independent tuning of mechanical strength and gelation rate. Soft Matter 2008; 4: 880-887.
49. Lee F, Chung JE, Kurisawa M,. An injectable hyaluronic acid-tyramine hydrogel system for protein delivery. J Control Release 2009; 134: 186-193.
50. Gupta D, Tator CH, Shoichet MS,. Fast-gelling injectable blend of hyaluronan and methylcellulose for intrathecal, localized delivery to the injured spinal cord. Biomaterials 2006; 27: 2370-2379.
51. Liu L, Liu D, Wang M, Du G, Chen J,. Preparation and characterization of sponge-like composites by cross-linking hyaluronic acid and carboxymethylcellulose sodium with adipic dihydrazide. Eur Polym J 2007; 43: 2672-2681.
52. Nakaji-Hirabayashi T, Kato K, Iwata H,. Hyaluronic acid hydrogel loaded with genetically-engineered brain-derived neurotrophic factor as a neural cell carrier. Biomaterials 2009; 30: 4581-4589.
53. Nie H, Liu M, Zhan F, Guo M,. Factors on the preparation of carboxymethylcellulose hydrogel and its degradation behavior in soil. Carbohydr Polym 2004; 58: 185-189.
54. Gong C, Shi S, Wu L, Gou M, Yin Q, Guo Q, Dong P, Zhang F, Luo F, Zhao X, et al. Biodegradable in situ gel-forming controlled drug delivery system based on thermosensitive PCL-PEG-PCL hydrogel. Part 2: Sol-gel-sol transition and drug delivery behavior. Acta Biomater 2009; 5: 3358-3370.
55. Bromberg LE, Ron ES,. Temperature-responsive gels and thermogelling polymer matrices for protein and peptide delivery. Adv Drug Deliv Rev 1998; 31: 197-221.
56. Ritger PL, Peppas NA,. A simple equation for description of solute release II. Fickian and anomalous release from swellable devices. J Control Release 1987; 5: 37-42.