Membrane Journal (멤브레인)

The Membrane Society of Korea (한국막학회)
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Application of Hyaluronic Acid Membrane Cross-linked with 1,3-Butadiene Diepoxide

1,3-Butadiene diepoxide로 가교된 히아루론산 막의 응용

  • Cheong, Seong-Ihl (Department of Chemical Engineering and Nano-Bio Technology, Hannam University) ;
  • Han, Gwang-Seon (Department of Chemical Engineering and Nano-Bio Technology, Hannam University) ;
  • Bae, Jung-Eun (Department of Biological Sciences, Hannam University) ;
  • Kim, In-Seop (Department of Biological Sciences, Hannam University)
  • 정성일 (한남대학교 나노생명화학공학과) ;
  • 한광선 (한남대학교 나노생명화학공학과) ;
  • 배정은 (한남대학교 생명과학과) ;
  • 김인섭 (한남대학교 생명과학과)
  • Published : 2008.06.30
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Abstract

The biodegradable hyaluronic acid membranes cross-linked with lactide using the crosslinking agent, 1,3-butadiene diepoxide (BD), were prepared as a potential biocompatible material for tissue engineering. The degree of lactide and BD reaction of the crosslinked membrane was determined by the analysis of nuclear magnetic resonance spectroscopy 6% of growth inhibition was observed in case of high BD concentration but the value is low enough not to affect cell growth. As the crosslinking reaction temperature increased, elongation increased and swelling ratio decreased. The rate of degradation was found to increase with the crosslinking temperature. The drug release experiment showed that the transport of drug through the membrane decreased with the crosslinking temperature.

조직공학용 생체 물질로 사용하고자 가교제 1,3-butadiene diepoxide (BD)를 사용하여 락타이드와 가교시킨 히아루론산 막을 제조하였다. 막의 락타이드 및 BD 반응도는 핵자기 공명 분광볍으로 결정하였다. BD 농도가 높을 경우 6%이하의 성장저해 현상이 나타났으나 그 값은 세포 성장에 문제되지 않을 정도로 충분히 낮았다. 가교온도가 낮을수록 탄성 율은 증가하고 팽윤도는 감소하였다. 막의 생분해속도는 가교온도가 낮을수록 감소하였다. 약물방출 실험 결과 가교 온도가 낮을수록 막을 통한 약물 투과는 감소하였다.

Keywords

References

  1. G. D. Prestwitch, D. M. Marecak, and J. F. Marecek, 'Controlled chemical modification of hyaluronin acid: synthesis, applications, and biodegradation of hydrazide derivatives', J. Control. Rel., 53, 93-103 (1998) https://doi.org/10.1016/S0168-3659(97)00242-3
  2. Y. Luo, K. R. Kirker, and G. D. Prestwich, 'Cross-linked hyaluronic acid hydrogel films: new biomaterials for drug delivery', J. Control. Rel., 69, 169-184 (2000) https://doi.org/10.1016/S0168-3659(00)00300-X
  3. S. N. Park, H. J. Lee, K. H. Lee, and H. Suh, 'Characterization of porous collagen/hyaluronic acid scaffold modified by 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide cross-linking', Biomaterials, 22, 1205-1212 (2002)
  4. S. N. Park, H. J. Lee, K. H. Lee, and H. Suh, 'Biological characterization of EDC-crosslinked collagen-hyaluronic acid matrix in dermal tissue restoration', Biomaterials, 24, 1631-1641 (2003) https://doi.org/10.1016/S0142-9612(02)00550-1
  5. H. S. Nam, J. H. Kim, J. H. An, and D. J. Jung, 'Synthesis of Hyaluronic acid scaffold for tissue engineering and evaluation of its drug release behaviors', Polymer(Korea), 25(4), 476-485 (2001)
  6. J. A. Hunt, H. N. Joshi, V. J. Stella, and E. M. Topp, 'Diffusion and drug release in polymer films prepared from ester derivatives of hyaluronic acid', J. Control. Rel., 12, 159-169 (1990) https://doi.org/10.1016/0168-3659(90)90092-8
  7. L. Benedetti, R. Cortivo, T. Berti, A. Berti, F. Pea, M. Marzzo, M. Moras, and G. Abatangel, 'Biocompatibility and biodegradation of different hyaluronan derivatives (Hyaff) implanted in rats', Biomateials, 14, 1154-1160 (1993)
  8. J. Aigner, J. Tegeler, P. Hutzler, D. Campoccia, A. Pavesio, C. Hammer, E. Kastenbauer, and A. Naurnann, 'Cartilage tissue engineering with novel nonwoven structured biomaterial based on hyaluronic acid benzyl ester', J. Biomed. Mater. Res., 42, 172-181 (1998) https://doi.org/10.1002/(SICI)1097-4636(199811)42:2<172::AID-JBM2>3.0.CO;2-M
  9. G. P. Chen, Y. Ito, Y. Imanishi, A. Magnani, S. Lamponi, and R. Barbucci, 'Photoimmobilization of sulfated hyaluronic acid for antithrombogenicity', Bioconjugate Chem., 8, 730-734 (1997) https://doi.org/10.1021/bc9700493
  10. S. K. Hahn and A. S. Hoffman, 'Characterization of Biocompatible Polyelectrolyte Complex Multlayer of Hyaluronic Acid and Poly-L-Lysine', Biotech. and Biopro. Eng., 9, 179 (2004) https://doi.org/10.1007/BF02942289
  11. C. Grandfils, P. Flandroy, and R. Jerome, 'Control of the biodegradation rate of poly(DL-lactide) microparticles intended as chemoembolization materials', J. Control. Rel., 38, 109-122 (1996) https://doi.org/10.1016/0168-3659(95)00102-6
  12. H. Fukuzaki, M. Yoshida, M. Asano, and M. Kumakura, 'Synthesis of copoly (D,L-lactic acid) with relatively low molecular weight and in vitro degradation', Eur. Polym. J., 25(10), 1019-1026 (1989) https://doi.org/10.1016/0014-3057(89)90131-6
  13. S. Li, M. Tenon, H. Garreau, C. Braud, and M. Vert, 'Enzymatic degradation of stereocopolymers derived from L-, D,L- and meso-lactides', Polym. Degrad. Stab., 67, 85-90 (2000) https://doi.org/10.1016/S0141-3910(99)00091-9
  14. J. Y. Kwon and S. I. Cheong, 'Characterization of hyaluronic acid membrane containing lactic acid', Membrane Journal, 15(1), 8-14 (2005)
  15. J. Y. Kwon and S. I. Cheong, 'Synthesis and characterization of hyaluronic acid bead crosslinked by 1,3-butadiene diepoxide', Polymer(Korea), 29(5), 445- 450 (2005)
  16. J. Y. Kwon and S. I. Cheong, 'Characterization of hyaluronic acid membrane crosslinked with lactide', Polymer(Korea), 29(6), 599-604 (2005)
  17. M. S. Kim, J. Y. Kwon, and S. I. Cheong, 'Synthesis of lactide/hyaluronic acid polymer membrane for the application of drug delivery system', Membrane Journal, 15(4), 281-288 (2005)
  18. W. J. Kim, J. Y. Kwon, S. I. Cheong, and I. S. Kim, 'Cytotoxicity of hyaluronic acid membrane crosslinked with lactide', Korean J. Biotechnol. Bioeng., 21(4), 255-259 (2006)
  19. T. C. Laurent, K. Hellsing, and B. Gelotte, 'Crosslinked gels of hyaluronic acid', Acta Chem. Scand., 18, 274-275 (1964) https://doi.org/10.3891/acta.chem.scand.18-0274
  20. B. Ronnebeger, W. J. Kao, J. M. Anderson, and T. Kissel, 'In vivo biocompatibility study of ABA triblock copolymers consisting of poly(L-lactic-coplycolic acid) A blocks attached to central poly (oxyethylene) B blocks', J. Biomed. Mater. Res. Part A, 30, 31-40 (1996) https://doi.org/10.1002/(SICI)1097-4636(199601)30:1<31::AID-JBM5>3.0.CO;2-S
  21. S. H. Oh, J. Y. Lee, S. H. Ghil, S. S. Lee, S. H. Yuk, and J. H. Lee, 'PCL microparticle-dispersed PLGA solution as a potential injectable urethral bulking agent', Biomaterials, 27, 1936-1944 (2006) https://doi.org/10.1016/j.biomaterials.2005.09.030
  22. T. Coviello, M. Dentini, G. Rambone, P. Desideri, and F. Alhaique, 'A novel crosslinked polysaccharide: studies for a controlled delivery matrix', J. Control. Rel., 55, 57-66 (1998) https://doi.org/10.1016/S0168-3659(98)00028-5