히알루론산에 결합된 리포산 자기조립체의 제조 및 특성

홍인림; 김영진; In Rim Hong; Young Jin Kim

Polymer(Korea), Vol.32, No.6, 561-565, November, 2008

Export Citation

히알루론산에 결합된 리포산 자기조립체의 제조 및 특성

Self-Aggregated Nanoparticles of Lipoic Acid Conjugated Hyaluronic Acid

홍인림, 김영진 ^{1, †}

충남대학교 공과대학 나노기술학과
¹충남대학교 공과대학 바이오응용화학과

In Rim Hong, and Young Jin Kim^{1, †}

Department of Nano Technology, Chungnam National University, 220, Gung-dong, Yuseong-gu, Daejeon 305-764, Korea
¹Department of Applied Chemistry & Biological Engineering, Chungnam National University, 220, Gung-dong, Yuseong-gu, Daejeon 305-764, Korea

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초록

본 연구에서는 천연고분자인 히알루론산(hyaluronic acid, HA)에 항산화제인 리포산(lipoic acid, LA)을 그래프트시켜 양친성 공중합체를 결합하였다. 이 공중합체는 수용액상에서 자기조립에 의해서 친수성인 히알루론산이 소수성인 리포산을 감싸는 형태의 고분자 입자를 형성한다. 히알루론산과 리포산을 결합하기 전에 adipic acid dihydrazide(ADH)을 이용하여 히알루론산의 카복실 부분을 개질시켰다. 히알루론산의 개질 분석과 HA-g-LA의 결합을 확인하기 위해 분광학적 분석방법을 이용하여 분석하였다. 형성된 입자는 DLS와 TEM을 사용하여 크기를 측정하였고 나노크기의 구조를 이룬다는 것을 확인하였다. 나노크기의 고분자 입자는 소수성 물질을 포함하는 전달체로 사용될 수 있다.

Hyaluronic acid (HA) is a natural glycosaminoglycan and is used widely in the pharmaceutical field. Lipoic acid (LA) helps the regeneration of exogenous and endogenous antioxidants such as Vitamin C and Vitamin E as well as glutathione. It also acts as antioxidant indirectly. Hydrophilic HA as a biodegradable and biocompatible polymer was conjugated with hydrophobic LA as an antioxidant to form the graft copolymer. The carboxyl group of HA was modified by adipic acid dihydrazide (ADH). The synthesis of HA-g-LA graft copolymers was characterized by FT-IR, 1H-NMR spectroscopy. The conjugates could form the self-assembled nanoparticles in aqueous solution. The particle size and critical aggregation concentration were verified to use the nanoparticle as a carrier for the hydrophobic material.

Keywords:hyaluronic acid;lipoic acid;graft copolymer;antioxidant

[References]

Gruzman A, Hidmi A, Katzhendler J, Haj-Yehie A, Sasson S, Bioorg. Med. Chem., 12, 1183 (2004)
Kofiji K, Nakamura M, Isobe T, Murata Y, Kawashima S, Food Chem., 109, 167 (2008)
Gonzalez-Perez O, Gonzalez-Castaneda RE, Nutr. Res., 26, 1 (2006)
Weeralkody R, Fagan P, Kosaraju SL, Int. J. Pharm., 357, 213 (2008)
Hahn SK, Oh EJ, Miyamoto H, Shimbouji T, Int. J. Pharm., 322, 44 (2006)
Hahn SK, Park JK, Tomimatsu T, Shimoboji T, Int. J. Bio. Macromol., 40, 374 (2007)
Ko YK, Kim SH, Jeong JS, Park JS, Lim JY, Kim MS, Lee HB, Khang G, Polym.(Korea), 31(6), 505 (2007)
Kim SJ, Hahn SK, Kim MJ, Kim DH, Lee YP, J. Control. Release, 104, 323 (2005)
Luo Y, Kirker KR, Prestwich GD, J. Control. Release, 69, 169 (2000)
Oh EJ, Kim JS, Hahn SK, Key Engineering Materials, 342, 525 (2007)
Palumbo F, Pitarresi G, Mandracchia D, Tripodo G, Giammona G, Carbohyd. Polym., 66, 379 (2006)
Wang YS, Liu LR, Zhang QQ, Eur. Polym. J., 43, 43 (2007)

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[1] Gruzman A, Hidmi A, Katzhendler J, Haj-Yehie A, Sasson S, Bioorg. Med. Chem., 12, 1183 (2004)

[2] Kofiji K, Nakamura M, Isobe T, Murata Y, Kawashima S, Food Chem., 109, 167 (2008)

[3] Gonzalez-Perez O, Gonzalez-Castaneda RE, Nutr. Res., 26, 1 (2006)

[4] Weeralkody R, Fagan P, Kosaraju SL, Int. J. Pharm., 357, 213 (2008)

[5] Hahn SK, Oh EJ, Miyamoto H, Shimbouji T, Int. J. Pharm., 322, 44 (2006)

[6] Hahn SK, Park JK, Tomimatsu T, Shimoboji T, Int. J. Bio. Macromol., 40, 374 (2007)

[7] Ko YK, Kim SH, Jeong JS, Park JS, Lim JY, Kim MS, Lee HB, Khang G, Polym.(Korea), 31(6), 505 (2007)

[8] Kim SJ, Hahn SK, Kim MJ, Kim DH, Lee YP, J. Control. Release, 104, 323 (2005)

[9] Luo Y, Kirker KR, Prestwich GD, J. Control. Release, 69, 169 (2000)

[10] Oh EJ, Kim JS, Hahn SK, Key Engineering Materials, 342, 525 (2007)

[11] Palumbo F, Pitarresi G, Mandracchia D, Tripodo G, Giammona G, Carbohyd. Polym., 66, 379 (2006)

[12] Wang YS, Liu LR, Zhang QQ, Eur. Polym. J., 43, 43 (2007)