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1 Journal of the Korean Chemical Society Printed in the Republic of Korea 열처리에의해가교된다공성키토산 - 알지네이트 - 젤라틴지지체의특성 Áw Á w Á Á Á * w yw q ³ w w w ( ) Characteristics of porous Chitosan-Alginate-Gelatin Scaffold Cross-linked by Heat-treatment Min Soo Choi, Hee Dong Han, Hasoo Seong, Eun Seok Park, Sang Cheol Chi, and Byung Cheol Shin* Bioactive Molecules Delivery & Control Research Team, Korea Research Institute of Chemical Technology, Daejeon , Korea College of Pharmacy, Sung Kyun Kwan University, Suwon , Korea (Received March 30, 2006). š œ» w w ƒ s w w w k. jm, p p œ ƒ w š w ƒ jš, ƒ œ w. FT-IR Ÿ mw œ ƒ š l w w x y w. œ 100~200 µmj» œ x w š, ƒ œ w 2 w. œ ƒ w œ w 130% w š, ƒ œ 11.3% w. ƒ k š œ w w œ w w. : œ, š,, œw ABSTRACT. Cross-linking agents used for enhancing mechanical properties of porous natural scaffolds, reduces biocompatability of the scaffolds, due to their inherent cytotoxicity. In this study, scaffolds which was composed of chitosan, alginate and gelatin were cross-linked by using heat treatment instead of cross-linking agent and mechanical properties of the cross-linked scaffold were investigated. Fourier transform infrared spectroscopy (FT-IR) analysis confirmed that cross-linking of heat-treated scaffold was formed via amide or ester linkage between the polymer chains. The heat-treated scaffold had interconnected pores with mean diameter of 100~200 µm and showed more than two fold increase of water uptake in comparison with chemically cross-linked scaffold. Tensile strength of the heat-treated scaffold increased up to 130% compared to non cross-linked scaffold and average maximum elongation was 11.3%. The porous cross-linked scaffold with the improved mechanical property may be suitable as a biocompatable scaffold for tissue engineering. Keywords: Porous scaffold, Natural polymer, Heat-treatment, Tissue engineering 224

2 š œ e, y e, w š. 1 p w r l, w s w w ww ü z ùkü w w ƒ š w. 2 s z xw» w w sƒ t w 3 x w œ ƒ w œ µm j» œ x w s wš s ww w. 3 w œ ü z y w š, z w w w š w. w, w, š» w œ v. 2,4 x œ š š g, p, p jm š s, s w, s ε-ev m, s l, s g, s p œ w w š ƒ š. 3~8 p œ š ey š ü ü w ù ü š œ š š. wr, š œ w» w ƒ š. œ š w j» yww w z w g w, 9 š s xk w, 10 š w k yww y z þ jš w y š. 3,4,11 w p w œ jm - p- p p 225»œ j» œ. w š w w œ w š w œ w w, w» ù w š ƒ w w. š 12 w ƒ yw mw» w j. yw ƒ 3~6, 13~15 EDC (N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride), k (glutaraldehyde), β-gp (β-glycerol-phosphate) š ƒ w x g w ƒ w wš» ƒ k. ù ƒ ƒ œ ü w ƒ w s ùk ý ü z ƒ w» w ùký. ƒ yw ù ƒ w š» ƒ j» w ƒ š. jm p p w w l w x œ w. œ š ƒ w x FT-IR mw y w š, t ü œ x w w. w œ, d w» p sƒw.»». œ w» w» š jm (75~85% k py, ; 5-20 cps), p( ; 250 cps), š p ƒƒ Showa Chem. Inc. (Kyoto, Japan), Sigma-Aldrich Co. (Mo, USA), š Yakuri Pure Chem. Co. (Kyoto, Japan) w w š x w š yw Fig. 1 ùkü. ƒ EDC Sigma-Aldrich Co. (MO, USA) w w. x w x

3 226 Áw Á w Á Á Á Fig. 1. Structure of natural polymers. (a) Chitosan (degree of deacetylation is 75~85 %), (b) Alginate and (c) Gelatin. p w.»». š yw w š» (Ultra-turrax T25, IKA Lab., Germany) w š, œ w»(fd5505s, Ilsin Lab, Korea) w. œ w d w» w»(companion Lab, SI-600, Korea) w. œ Ì Dial indicator ( , IDS TYPE) w d w š, œ x (Model S-2250N, Hitachi Co., Japan) w w. œ y w Fourier transform infrared spectrophotometry (FT-IR, FT 165, Bio-Rad, USA) w w š»(instron 4482, Instron Co., MA, USA) w d w. œ jm, p p œ w» w 2% (w/v) jm, 2% (w/v) p, š 2% (w/v) p ƒƒ w. jm 3% (v/v) p ww. 2% (w/v) w jm, p, p 6:2:2 v 5 mlƒ ywwš š» w 13,000 rpm 10 z»s w» w 4 C o 12 w. yw 5 ml 55 mm š -20 C þ k z o» w 3 w. x œ œ w w w z œ 80 C 12 w o w. ƒ EDC w ƒ w œ œ w 13 w. 90% (v/v) k 0.3% (w/v) w EDC 100 ml œ e w z 25 o C, 100 rpm» 24 ƒ g. ƒ œ p, EDC k w» w 300 ml 20 w 3z w. w œ -20 o C þ k z 3 w ƒ œ w. œ FT-IR d œ œ t w gqw x w. wr,, š ƒ œ š wx w» w w FT-IR w Ÿ w. œ œ w 2 cm 2 cm j» w, š ƒ w œ (ph 7.4, 80 ml) e w 37 o C 200 rpm z w» 3 k z xk w sƒw. œ 2 cm 2 cm w d w z, 60 Journal of the Korean Chemical Society

4 w œ jm - p- p p 227 e w Éü z d w (1) w w. W Water Uptake, Wu = w W d (1) W d Ww œ š W d w œ. œ œ» w» w d w. œ 3cm 1cm j» w r Ì d w z Ì s w w. r ó š wš» w 0.5 mm/s r w š q (2) (3) w w. Tensile strength (KPa, 10 3 N/m 2 )= Load( N) (2) Cross sectional Area( m 2 ) ( e Maximum elongation (%) = t e i ) (3) (2) σ q š d q r Ì. wr (3) ei š e t q r ¼. m œ w w FT-IR Fig. 2, ƒ œ FT-IR Ÿ w ùkü. jm, p p 3 œ rp 1654 cm -1 Iv j, 1549 cm -1 II, 1406 cm -1 e» vj, 1100 cm -1 l w vj š 1075 cm -1 fm vj y w. œ rp œ rp w ù vj. œ I w vjƒ ƒ e i Fig. 2. FT-IR spectra of Chitosan-Alginate-Gelatin scaffolds. (a) Control scaffold, (b) Heat-treated scaffold and (c) Crosslinked scaffold. w w w ƒ y w. wr, ƒ œ I, l w, š fm» w vj j» ƒ ƒwš e» w vjƒ w y w. ƒ œ l w fm» w vjƒ ƒwš e» w vj j»ƒ w p p e» jm p» EDC w w w» ƒ. ƒ œ ƒ yw w w y ù, œ w w l w š ƒ w x q. œ t Fig. 3, ƒ œ ƒƒ t x w. Fig. 3(a) ùkù œ t ñ t k x»œ š, Fig. 3(b) ù kü œ t µm j» w»œ x. Fig. 3(c) ùkü ƒ œ t t ƒ w e xk»œ. w y k xk w k

5 최민수 한희동 성하수 박은석 지상철 신병철 SEM images of the surface of Chitosan-Alginate-Gelatin scaffolds. (a) Control scaffold, (b) Heat-treated scaffold and (c) Cross-linked scaffold (original magnification of 150). Fig 키는 방법으로서, 지지체 용액을 동결시키는 과정에 서 형성된 지지체 표면 막에 기공을 형성시킨다. 지 지체에 형성된 기공은 지지체 내부로 필요한 세포와 영양분을 이동시키는 이동로 역할을 한다. 따라서 다 공성 지지체 표면에 기공이 없을 경우에는 세포와 영 양분의 이동이 용이하지 않아 세포증식이 원활하지 못한 문제점이 야기된다. 그러므로 다공성지지체 내 부로 세포와 영양분의 이동이 원활하게 해주기 위해 서는 다공성 지지체 표면에 많은 기공을 형성시켜야 한다. 본 연구에서 제조된 다공성 지지체는 동결과 정에서 표면에 막을 형성한다. 따라서 대조군 지지 체의 기공은 표면에 형성된 막에 동결건조 과정에서 승화된 물이 외부로 방출되기 위하여 형성된 통로이 다. 그러나 가교처리 다공성 지지체는 제조과정을 고 려할 때 1차 동결건조에서 형성된 기공구조가 가교 반응에 의해 닫힌 것으로 생각된다. 반면, 열처리 다 공성 지지체는 열처리 과정에서 증발되는 초산 기체 11 가 표면에 형성된 기공의 수와 면적을 증가시켜 가 장 많은 기공을 형성한 것으로 판단된다. 다공성 지지체의 단면구조 는 대조군, 열처리 및 가교처리 다공성 지지 체의 단면 구조를 주사전자 현미경으로 관찰한 사진 이다. 대조군, 가교처리 및 열처리 다공성 지지체의 단면공극의 크기는 각각 150, 200 그리고 200 µm의 연속적인 열린 구조의 형태를 이루고 있는 것을 확 인하였다. 특히 가교처리와 열처리한 다공성 지지체 의 공극 모양은 대조군 다공성 지지체의 공극에 비 하여 구형에 가까운 형태임을 확인하였다. 한편, Doillon 등은 다공성 지지체의 기공이 연속적으로 형 성된 열린 구조일 때 섬유아세포가 빠르게 이동하여 조직재생을 촉진한다고 보고하였다. 이것은 연속적 으로 연결된 공극사이를 섬유아세포와 영양분이 빠 르게 이동하여 조직 형성을 촉진하기 때문이다. 따 Fig Cross-sectional SEM images of Chitosan-Alginate-Gelatin scaffolds. (a) Control scaffold, (b) Heat-treated scaffold and (c) Cross-linked scaffold (original magnification of 80). Fig Journal of the Korean Chemical Society

6 열처리한 다공성 키토산 알지네이트 젤라틴 지지체의 특성 - 라서 다공성 지지체 공극의 열린 구조는 세포의 부 착과 증식에 중요한 요소이다. 대조군 다공성 지지 체의 공극이 타원형의 구조를 갖는 것에 반하여 열 처리와 가교처리한 다공성 지지체의 공극이 구형이 고, 크기가 50 µm 이상 증가한 것은 공극의 외벽이 아미드 결합이나 에스테르 결합에 의해 가교되었기 때문인 것으로 생각된다. 대조군 다공성 지지체에 잔 류하는 미량의 초산은 공기 중의 수분접촉 만으로도 지지체의 강도를 약화시켜 공극의 외벽이 무너지고 수축현상이 나타나 결과적으로 지지체의 공극을 파 괴시킨다. 반면, 열처리와 가교처리 다공성 지지체는 아미드 결합 또는 에스테르 결합에 의해 연결된 공 극구조를 가짐으로써 강도가 증가하여 공극의 외벽 이 무너지지 않고 수축현상이 발생하지 않아 공극의 구조를 유지할 수 있는 것으로 생각된다. 특히, 열처 리 다공성 지지체는 가교제를 사용하지 않고 부분적 인 아미드 결합 또는 에스테르 결합이 형성되어 수 분으로 인한 공극의 수축현상을 일으키지 않으면서 형태를 유지할 수 있어 세포와 영양분의 공급이 원 활한 열린 구조를 유지하는 것을 관찰하였다 다공성 지지체의 안정성 다공성 지지체의 수분에 대한 안정성을 조사하기 위하여 각각의 다공성 지지체를 37 C에서 인산염 완 충용액에 침지하여 3시간 교반한 후의 형태를 관찰 하였고 그 결과를 Fig. 5에 나타내였다. 대조군 다공 성 지지체는 인산염 완충용액 내에서 용해되어 형태 를 관찰할 수 없었다. 그러나 열처리 다공성 지지체 와 가교처리한 다공성 지지체는 인산염 완충용액 내 o 에서 용해되지 않고 고유의 형태를 유지하였고, 자 료로 제시하지는 않았으나 24시간 후에도 고유의 형 태를 유지하고 있었다. 세포는 다공성 지지체의 내 부벽면에 부착한 후 증식하여 일정한 형태와 기능을 갖춘 조직으로 형성된다. 따라서 다공성 지지체는 조 직이 형성되면서 생분해될 수 있어야 하나 세포가 부 착하고 증식하는 동안 혈액이나 수분에 의해 급격히 분해되지 않고 형태를 유지하여야 한다. 그러므로 열 처리 다공성 지지체와 가교처리 다공성 지지체는 수 분에 의해 급격히 분해되지 않고 세포가 증식하는 동 안 안정한 형태를 유지할 수 있을 것으로 생각된다. 고분자 사슬간의 인력이 존재하지 않는 대조군 다 공성 지지체는 인산염 완충 용액에서 쉽게 용해되어 형태를 유지할 수 없다. 그러나 가교처리 다공성 지 지체는 EDC에 의해 활성화된 알지네이트의 카르복 실기가 키토산또는 젤라틴과 공유결합을 형성하면서 고분자 사슬간의 가교결합을 형성하여 수분에 의해 용해되지 않았다. 특히, 열처리 다공성 지지체가 인 산염 완충 용액에 용해되지 않는 것은 80 C에서 열 처리하여 고분자 사슬간에 부분적인 아미드 결합 또 는 에스테르 결합이 형성되었기 때문으로 생각된다. o 16 수분흡수력 다공성 지지체의 수분흡수력은 체내에 이식된 다 공성 지지체가 혈액 속에 포함된 세포를 수용할 수 있는 능력을 결정하는 중요한 요소이다. Fig. 6에 본 연구에서 제조된 다공성 지지체의 수분흡수도를 나 타내었으며 가교처리와 열처리 다공성 지지체의 수 분흡수도는 각각 60.13과 로써 열처리 다공성. 5. Morphology of Chitosan-Alginate-Gelatin scaffolds in PBS buffer solution at 37 oc after 3 hours incubation. (a) Control scaffold, (b) Heat-treated scaffold and (c) Cross-linked scaffold. Fig

7 230 Áw Á w Á Á Á Fig. 6. Water uptake (Wu) of heat-treated or cross-linked scaffolds. ( ý ) Cross-linked scafold and ( þ ) Heat-treated scaffold. ƒ ƒ œ w 2 ùkü. wr, œ w d ƒ w (Fig. 5). w EDC w e y ƒ». Fig. 4 ùkù ƒ t ü ww ƒ w ƒ w., œ ü ƒ t w»œ mw yw» ƒ ƒw. w œ Table 1 ù kü, ƒ œ ƒƒ 8.1Û1.5 KPa, 10.7Û2.5 KPa š 12.8Û3.1 KPa. r ƒw ùkü. ƒ œ Table 1. Tensile strength and maximum elongation of Chitosan-Alginate-Gelatin scaffolds Scaffold Tensile strength (KPa, 10 3 N/m 2 ) Maximum elongation (%) Control 8.1± ±1.3 Heat-treated 10.7± ±3.60 Cross-linked 12.8± ±0.8 œ w ƒ 4.7 KPa ƒw ƒ š. ƒ w w š w ƒw». wr, œ ƒ œ w ƒ û ù œ w 2.6 KPa w k y w. wr,,, ƒ œ 8.4Û1.3%, 11.3Û3.6% š 4.9Û 0.77%. œ œ w 3% ƒw ù ƒ œ 3.5% w. œ (entanglement) w w w l w ƒ ƒ ƒ» ƒ ƒ. ù ùe ƒ ƒ g ƒw š Á x w. ƒ œ ƒ Á x ùkù w. œ ƒ w ƒ w w k ü ù q x w q w. ü w w š š w w l w x w. œ w w w š, ƒ œ w 2 ƒ w. w œ œ j» sƒ x w» w yw w 100~200 µm ùkü y wš ƒ g ü œ q yw. ƒ k œ» yw ƒ w Journal of the Korean Chemical Society

8 w œ jm - p- p p 231 w wš, ƒ ƒ k œw y».. x 1. Lee, S. B.; Joen, H. W.; Lee, Y. W.; Lee, Y. M.; Song, K. W.; Park, M. H. Y.; Nam, S.; Ah/n, H. C. Biomaterials 2003, 24, Pierre, S.; Xavier, Roy; Basil. D. F. Biomaterials 2004, 25, Shin, H. W.; Kim, S. H.; Jang, J. W.; Kim, M. S.; Cho, S. H.; Lee, H. B.; Khang, K. S. Polymer(Korea) 2004, 28, Jeon, E. K.; Whang, H. J.; Kang, G. G.; Lee, I.; Rhee, J. M.; Lee, H. B. Polymer(Korea) 2001, 25(6), Choi, Y. S.; Hong S. R.; Lee, Y. M.; Song, K. W.; Park, M. H.; Nam, Y. S. Int. J. Bioed. Mater. Res. 1999, 23, Yilmaz, G.; Jongboom R. O. J.; Feil, H.; Hennink, W.E. Carbohyd. Polym. 2001, 45, Choi, M. S.; Han, H. D.; Kim, T. W.; Song, C. K.; Park, E. S.; Shin, B. C. J. Kor. Pharm. Sci. 2005, 35, Caren, C.; Bernd, W. M. Int. J. Pharm. 2000, 194, Jang, J. W.; Lee, B.; Han, C. W.; Lee, I. W.; Lee, H. B.; Khang, K. S. Polymer(Korea) 2003, 27, Bhattarai, N.; Edmondson, D.; Veiseh, O.; Matsen, F. A.; Zhang, M. Biomaterials 2005, 26, Choi, Y. S.; Lee, S. B,; Hong S. R.; Lee, Y. M.; Song, K. W.; Park M. H. J. Mater. Sci. 2001, 12, Li, Z.; Ramay, H. R.; Hauch, K. D.; Xiao, D.; Zhang, M. Biomaterials, 2005, 26, Mao, J. S.; Liu, H. F.; Yin, Y. J.; Yao, K. D. Biomaterials 2003, 24, Smitha, B.; Sridhar, S,; Khan, A. A. Eur. Polym. J. 2005, 41, Park, S. N.; Park, J. C.; Kim, H. O.; Sung, M. J.; Suh, H. Biomaterials 2002, 23, Pitthidej, G. C.; Phaechamud, T.; Koizumi, T. Int. J. Pharm. 2002, 232, Doillon C. H.; Silver, F. H. Biomaterials 1986, 7, 3.

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