Article
  • Synthesis and Characteristic of Cross-linked Hyaluronic Acid Hydrogels with Putrescine under the Neutral pH Condition

  • Yu Rim Je*, **, So Ra Bang*, Il Keun Kwon**, Sang Jun Park*, and Chun-Ho Kim*,†

  • *Laboratory of Tissue Engineering, Korea Institute of Radiological Medical Sciences, Seoul 01812, Korea
    **Department of Dentistry, Graduate School, Kyung Hee University, 26 Kyungheedae-ro, Dongdaemum-gu, Seoul 02447, Korea

  • Putrescine의 존재 하에 중성 pH 조건에서의 가교 히알루론산 하이드로젤의 합성 및 특성

  • 제유림*, ** · 방소라* · 권일근** · 박상준* · 김천호*,†

  • *한국원자력의학원 방사선의학연구소, **경희대학교 치과대학 치의학과

  • Reproduction, stored in a retrieval system, or transmitted in any form of any part of this publication is permitted only by written permission from the Polymer Society of Korea.

References
  • 1. Collins, M. N.; Birkinshaw, C. Hyaluronic Acid Based Scaffolds for Tissue Engineering-A Review. Carbohyd. Polym. 2013, 92, 1262-1279.
  •  
  • 2. Jung, S. W.; Oh, S. H.; Lee, I. S.; Byun, J.-H.; Lee, J. H. In situ Gelling Hydrogel with Anti-bacterial Activity and Bone Healing Property for Treatment of Osteomyelitis. Tissue Eng. Regen. Med. 2019, 16, 479-490.
  •  
  • 3. Im, G.-I. Perspective on Intra-articular Injection Cell Therapy for Osteoarthritis Treatment. Tissue Eng. Regen. Med. 2019, 1-7.
  •  
  • 4. Lyu, H.-Z.; Lee, J. H. The Efficacy of rhBMP-2 Loaded Hydrogel Composite on Bone Formation Around Dental Implants in Mandible Bone Defects of Minipigs. Biomaterials Res. 2020, 24, 5.
  •  
  • 5. Choi, J.-S.; Oh, S. H.; Kim, Y.-M.; Lim, J.-Y. Hyaluronic Acid/alginate Hydrogel Containing Hepatocyte Growth Factor and Promotion of Vocal Fold Wound Healing. Tissue Eng. Regen. Med. 2020, 17, 651-658.
  •  
  • 6. Min, S.-J.; Kim, S.-W.; Lee, T.-H.; Kwon, I.-K.; Son, T.-I. Preparation of Injectable Hydrogels Immobilized with FGF Using UV-curable Hyaluronic Acid Derivatives. Polym. Korea 2020, 44, 451-458.
  •  
  • 7. Sung, Y. K.; Kim, S. W. Recent Advances in Polymeric Drug Delivery Systems. Biomaterials Res. 2020, 24, 1-12.
  •  
  • 8. Yang, J.-M.; Kim, H.-J.; Cho, B.-K. Preparation of Antioxidant Hydrogel Contact Lenses Based on Interpenetrating Hyaluronic Acid Network, Polym. Korea 2020, 44, 21-29.
  •  
  • 9. Hong, B. M.; Park, S. A.; Park, W. H. Effect of Photoinitiator on Chain Degradation of Hyaluronic Acid. Biomaterials Res. 2019, 23, 1-8.
  •  
  • 10. Xu, X.; Jha, A. K.; Harrington, D. A.; Farach-Carson, M. C.; Jia, X. Hyaluronic Acid-based Hydrogels: from a Natural Polysaccharide to Complex Networks. Soft Mater. 2012, 8, 3280-3294.
  •  
  • 11. Khunmanee, S.; Jeong, Y.; Park, H. Crosslinking Method of Hyaluronic-based Hydrogel for Biomedical Applications. J. Tissue Eng. 2017, 8, 2041731417726464.
  •  
  • 12. Yang, B.; Guo, X.; Zang, H.; Liu, J. Determination of Modification Degree in BDDE-modified Hyaluronic Acid Hydrogel by SEC/MS. Carbohyd. Polym. 2015, 131, 233-239.
  •  
  • 13. Shimojo, A. A.; Pires, A.; Lichy, R.; Santana, M. H. The Performance of Crosslinking with Divinyl Sulfone as Controlled by the Interplay between the Chemical Modification and Conformation of Hyaluronic Acid. J. Brazil. Chem. Soc. 2015, 26, 506-512.
  •  
  • 14. Ibrahim, S.; Kang, Q. K.; Ramamurthi, A. The Impact of Hyaluronic Acid Oligomer Content on Physical, Mechanical, and Biologic Properties of Divinyl Sulfone‐crosslinked Hyaluronic Acid Hydrogels. J. Biomed. Mater. Res. A 2010, 94, 355-370.
  •  
  • 15. Calles, J. A.; Ressia, J. A.; Llabot, J. M.; Vallés, E. M.; Palma, S. D. Hyaluronan–itaconic Acid–glutaraldehyde Films for Biomedical Applications: Preliminary Studies. Sci. Pharm. 2016, 84, 61-72.
  •  
  • 16. Kirk, J. F.; Ritter, G.; Finger, I.; Sankar, D.; Reddy, J. D.; Talton, J. D.; Nataraj, C.; Narisawa, S.; Millán, J. L.; Cobb, R. R. Mechanical and Biocompatible Characterization of a Cross-linked Collagen-hyaluronic Acid Wound Dressing. Biomatter 2013, 3, e25633.
  •  
  • 17. Cao, W.; Sui, J.; Ma, M.; Xu, Y.; Lin, W.; Chen, Y.; Man, Y.; Sun, Y.; Fan, Y.; Zhang, X. The Preparation and Biocompatible Evaluation of Injectable Dual Crosslinking Hyaluronic Acid Hydrogels as Cytoprotective Agents. J. Mater. Chem. B 2019, 7, 4413-4423.
  •  
  • 18. Nakajima, N.; Ikada, Y. Mechanism of Amide Formation by Carbodiimide for Bioconjugation in Aqueous Media. Bioconjugate Chem. 1995, 6, 123-130.
  •  
  • 19. Bulpitt, P.; Aeschlimann, D. New Strategy for Chemical Modification of Hyaluronic Acid: Preparation of Functionalized Derivatives and Their Use in the Formation of Novel Bio- compatible Hydrogels. J. Biomed. Mater. Res. A 1999, 47, 152-169.
  •  
  • 20. Kunishima, M.; Kawachi, C.; Monta, J.; Terao, K.; Iwasaki, F.; Tani, S. 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methyl-Morpho- linium Chloride: An Efficient Condensing Agent Leading to the Formation of Amides and Esters. Tetrahedron 1999, 55, 13159-13170.
  •  
  • 21. Farkaš, P.; Bystrický, S. Efficient Activation of Carboxyl Polysaccharides for the Preparation of Conjugates. Carbohyd. Polym. 2007, 68, 187-190.
  •  
  • 22. Raw, S. A. An Improved Process for the Synthesis of DMTMM-Based Coupling Reagents. Tetrahedron Lett. 2009, 50, 946-948.
  •  
  • 23. D’este, M.; Eglin, D.; Alini, M. A Systematic Analysis of DMTMM vs EDC/NHS for Ligation of Amines to Hyaluronan in Water. Carbohyd. Polym. 2014, 108, 239-246.
  •  
  • 24. Til, H.; Falke, H.; Prinsen, M.; Willems, M. Acute and Subacute Toxicity of Tyramine, Spermidine, Spermine, Putrescine and Cadaverine in Rats. Food Chem. Toxicol. 1997, 35, 337-348.
  •  
  • 25. Farriol, M.; Segovia-Silvestre, T.; Castellanos, J. M.; Venereo, Y.; Orta, X. Role of Putrescine in Cell Proliferation in a Colon Carcinoma Cell Line. Nutrition 2001, 17, 934-938.
  •  
  • 26. Seliktar, D. Designing Cell-compatible Hydrogels for Biomedical Applications. Science 2012, 336, 1124-1128.
  •  
  • 27. Tomihata, K.; Ikada, Y. Crosslinking of Hyaluronic Acid with Water‐soluble Carbodiimide. J. Biomed. Mater. Res. B 1997, 37, 243-251.
  •  
  • Polymer(Korea) 폴리머
  • Frequency : Bimonthly(odd)
    ISSN 0379-153X(Print)
    ISSN 2234-8077(Online)
    Abbr. Polym. Korea
  • 2023 Impact Factor : 0.4
  • Indexed in SCIE

This Article

  • 2021; 45(4): 601-609

    Published online Jul 25, 2021

  • 10.7317/pk.2021.45.4.601
  • Received on Mar 18, 2021
  • Revised on Apr 16, 2021
  • Accepted on Apr 21, 2021

Correspondence to

  • Chun-Ho Kim

  • Laboratory of Tissue Engineering, Korea Institute of Radiological Medical Sciences, Seoul 01812, Korea

  • E-mail: chkim@kcch.re.kr