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Characterization of Cross Linked Hyaluronic Acid Microbeads by Divinyl Sulfone

Divinyl Sulfone으로 가교된 히알루론산 마이크로비드의 특성평가

  • Kim, Jin-Tae (Department of Advanced Material Engineering, Chungbuk National University) ;
  • Lee, Deuk Yong (Department of Material Engineering, Daelim University) ;
  • Jang, Ju-Woong (Cellumed Co., Ltd.) ;
  • Kim, Tae-Hyung (Department of Radiological Science, Kangwon National University) ;
  • Jang, Yong-Wun (Department of Material Engineering, Daelim University)
  • Received : 2013.04.05
  • Accepted : 2013.06.28
  • Published : 2013.09.30

Abstract

Hyaluronic acid(HA) microbeads were synthesized by dropping the sodium hyaluronate(Streptococcus) solutions in NaOH into a solution mixture of divinyl sulfone(DVS) in 2-methyl-1-propanol, followed by stirring, cleaning and drying process at room temperature. The initial experimental conditions are crosslinking time(CLTi) of 5 h, crosslinking temperature(CLTe) of room temperature, injection air pressure(IAPr) of 5 psi, and DVS concentration( DVSc) of 0.2 vol%, respectively. Then, parametric studies were performed by varying the parameters to investigate the morphology, the porosity, the swelling ratio and the size of the beads. The microbead size pattern was not regular to function of the degree of crosslink. It was observed that the swelling ratio, the degree of crosslink, and the pore size can be controlled by adjusting the CLTi, CLTe and DVSc. Among the parameters investigated, the smallest bead size can be achieved by varying the CLTi parameter. The lowest swelling ratio, as an indication of the highest degree of crosslink, can be obtained by varying CLTe.

Keywords

References

  1. Chiara Schiraldi, Annalisa La Gatta and Mario De Rosa, "Biotechnological Production and Application of Hyaluronan", In Biopolymers; Elnashar, M., Ed.; Rijeka, Croatia, 387-412, 2010.
  2. S.P. Zhong, D. Campoccia, P.J. Doherty, R.L. Williams, L. Benedetti, D.F. Williams, "Biodegradation of hyaluronic acid derivative by hyaluronidase", Biomaterials. vol. 15, no. 5, pp. 359-365, 1994. https://doi.org/10.1016/0142-9612(94)90248-8
  3. Y. Tokita, A. Okamoto, "Hydrolytic degradation of hyaluronic acid", Polymer Degradation and Stalility. vol. 48, no. 2, pp. 269-273, 1995. https://doi.org/10.1016/0141-3910(95)00041-J
  4. A.M. Afify, M. Stern, M. Guntenhoner, R. Stern, "Purification and characterization of human serum hyaluronidase", Biochem Biophys. vol. 305, no. 2, pp. 434-441, 1993. https://doi.org/10.1006/abbi.1993.1443
  5. Oju Jeon, Su Jin Song, Kee-Jung Lee, Moon Hyang Park, Soo-Hong Lee, Sei Kwang Hahn, Sungjee Kim, Byung-soo Kim, "Mechanical properties and degradation behaviors of hyaluronic acid hydrogels cross-linked at various cross-linking densites", Carbohydrate Polymers, vol. 70, pp. 251-257, 2007. https://doi.org/10.1016/j.carbpol.2007.04.002
  6. Si-Nae Park, Jong-Chul Park, Hea Ok Kim, Min Jung Song, Hwal Suh, "Characterization of porous collagen/hyaluronic acid scaffold modified by 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide cross-linking", Biomaterials, vol. 23, pp. 1205-1212, 2002. https://doi.org/10.1016/S0142-9612(01)00235-6
  7. Yi Luo, Kelly R. Kirker, Gelnn D. Prestwich, "Cross-linked hyaluronic acid hydrogel films: new biomateirals for drug delivery", J. of Controlled Release, vol. 69, pp. 169-184, 2000. https://doi.org/10.1016/S0168-3659(00)00300-X
  8. Xiao Zheng Shu, Yanchun Liu, Yi Luo, Meredith C. Roberts, Glenn D. Prestwich, "Disulfied Cross-Linked Hyaluronan Hydrogels", Biomacromolecules, vol. 3, pp. 1304-1311, 2002. https://doi.org/10.1021/bm025603c
  9. Jin-Tae Kim, Jae-Ha Choi, Deuk-Yong Lee, "Pyrogenicity of hyaluronic acid hydrogel cross-linked by divinyl sulfone for soft tissue augmentation", Natural Science, vol. 2, no. 7, pp. 764-768, 2010. https://doi.org/10.4236/ns.2010.27096
  10. Sei Kwang Hahn, Jung Kyu Park, Takashi Tomimatsu, Tsuyoshi Shimoboji, "Synthesis and degradation test of hyaluronic acid hydrogels", Inter. J. of Biological Macromolecules, vol. 40, pp. 374-380, 2007. https://doi.org/10.1016/j.ijbiomac.2006.09.019
  11. Kenji Tomihata, Yoshito Ikada, "Preparation of cross-linked hyaluronic acid films of low water content", Biomaterials, vol. 18, pp. 189-195, 1997. https://doi.org/10.1016/S0142-9612(96)00116-0
  12. Jin Tae Kim, Deuk Yong Lee, Jae Ha Choi, "Preparation and Characterization of Hyaluronic Acid Microbeads", Biomaterials Research, vol. 14, no. 4, pp. 157-160, 2010.
  13. A. Pourjavadi, M. Ayyari, M.S. Amini-Fazl, "Taguchi optimized synthesis of collagen-g-poly(acrylic acid)/kaolin composite superabsorbent hydrogel", European Polymer Journal, vol. 44, pp. 1209-1216, 2008. https://doi.org/10.1016/j.eurpolymj.2008.01.032
  14. Ji Young Kwon, Seong Ihl Cheong, "Synthesis and Characteristics of Hyaluronic Acid Bead Crosslinked by 1,3-Butadiene diepoxide", Polymer(Korea), vol. 29, no. 5, pp. 445- 450, 2005.
  15. Chirag B. Shah, Stanley M. Barnett, "Swelling Behavior of Hyaluronic Acid Gels", J. of Applied Polymer Science, vol. 45, pp. 293-298, 1992. https://doi.org/10.1002/app.1992.070450211
  16. F.A. Korkoosh, J. Brussee, J.C. Verhoef, F. Borchard, M. Rafiee-Tehrani, H.E. Junginger, "Preparation and NMR characterization of superporous hydrogels(SPH) and SPH composites", Polymer, vol. 41, pp. 8213-8220, 2000. https://doi.org/10.1016/S0032-3861(00)00200-7
  17. Jun Chen, Haesun Park, Kinam Park, "Synthesis of superporous hydrogels: Hydrogels with fast swelling and superabsorbent properties", J. of Biomed. Mater. Res., vol. 44, pp. 53-62, 1999. https://doi.org/10.1002/(SICI)1097-4636(199901)44:1<53::AID-JBM6>3.0.CO;2-W
  18. Richard A. Gemeinhart, Haesun Park and Kinam Park, "Pore Structure of Superporous Hydrogels", Polym. Adv. Technol., vol. 11, pp. 617-625, 2000. https://doi.org/10.1002/1099-1581(200008/12)11:8/12<617::AID-PAT12>3.0.CO;2-L
  19. Hossein Omidian, Jose G. Rocca, Kinam Park, "Advances in superporous hydrogels", J. of Controlled Release, vol. 102, pp. 3-12, 2005. https://doi.org/10.1016/j.jconrel.2004.09.028
  20. Hetal Patel, Minal Bonde, Ganga Srinivasan, "Biodegradable Polymer Scaffold for Tissue Engineering", Trends Biomater. Artif. Organs, vol. 25, no. 1, pp. 20-29, 2011.
  21. Jin Tae Kim, Deuk Yong Lee, Jae Ha Choi, "Short Term Toxicity test of Tissue Augmentation Materials by Hyaluronic Acid Micro Bead", Biomaterials Research, vol. 14, no. 1, pp. 25-29, 2010.
  22. Jin Tae Kim, Deuk Yong Lee, Jae Ha Choi, "Implanting Test of Re-hydrated Hydrogels by Hyaluronic acid Microbeads", Biomaterials Research, vol. 15, no. 3, pp. 125-128, 2011.
  23. Jin Tae Kim, Jae Ha Choi, "Production and Evaluation of Hyaluronic Acid Gel for Soft Tissue Augmentation", Biomaterials Research, vol. 13, no. 3, pp. 105-108, 2009.
  24. J.T. Kim, C.H. Kook, J.H. Choi, "Production Equipment and Method of Polymer Gel for Bio-Implanting", J. of Korean Soc. of Mechanical Technology, vol. 11, no. 3, pp. 89-94, 2009. https://doi.org/10.17958/ksmt.11.3.200909.89
  25. "Manufacturing process of cationic polymer/hyaluronic acid microbead and cationic polymer/hyaluronic acid microbead chelated with metal ion highly containing hyaluronic acid in the inside of microbead, and cationic polymer/hyaluronic acid microbead chelated with metal ion manufactured by the same" 1020110135690A, patent of Korea.
  26. "Microbeads of natural polysaccharide and hyaluronic acid and processes for preparing the same", PCT/KR2003/001716.
  27. "Microbead of hyaluronic acid derivatives for medical purpose and process for preparing the same", 1020070012002, patent of Korea.
  28. J.T. Kim, D.Y. Lee, Y.S. Oh, J.W. Bang, C.Y. Hyun, T.H. Kim, "Swelling Properties for Cross-Linking Degree of Hyaluronic Acid Hydrogels", Biomaterials Research, vol. 17, no. 1, pp. 37-40, 2013.

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