Potent anti-adhesion agent using a drug-eluting visible-light curable hyaluronic acid derivative

Ga-Dug Han; Jae-Won Kim; Seung-Hyun Noh; Shin-Woong Kim; Eui-Chan Jang; Jae-Woon Nah; Young-Gi Lee; Mi-Kyung Kim; Yoshihiro Ito; Tae-Il Son

Journal of Industrial and Engineering Chemistry, Vol.70, 204-210, February, 2019

DOI10.1016/j.jiec.2018.10.017 Export Citation

Potent anti-adhesion agent using a drug-eluting visible-light curable hyaluronic acid derivative

Ga-Dug Han, Jae-Won Kim, Seung-Hyun Noh, Shin-Woong Kim, Eui-Chan Jang¹, Jae-Woon Nah², Young-Gi Lee³, Mi-Kyung Kim⁴, Yoshihiro Ito⁵, and Tae-Il Son^†

Department of Systems Biotechnology, Chung-Ang University, Anseong-si, Gyeonggi-do, Republic of Korea
¹Department of Orthopaedic Surgery, College of Medicine, Chung-Ang University Hospital, College of Medicine, 224-1 Heukseok-dong, Dongjak-gu, Seoul 156-755, Republic of, Korea
²Department of Polymer Science and Engineering, Sunchon National University, 255 Jungang-ro, Suncheon, Jeonnam 57940, Republic of Korea
³Department of Electronic Materials, Samsung SDI Company Ltd., Suwon 443-803, Republic of Korea
⁴Department of Pathology, College of Medicine, Chung-Ang University, Seoul 156-756, Republic of Korea
⁵Nano Medical Engineering Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan

E-mail:

Post-operative adhesion is a very serious complication in the clinical field, frequently occurring after surgery. In severe cases, reoperation may be required. In this study, a visible light-curable furfuryl hyaluronic acid derivative was prepared and combined with ibuprofen for anti-adhesion and antiinflammatory applications. A furfuryl isocyanate moiety was introduced in hyaluronic acid affording furfuryl hyaluronic acid (F-HA). The anti-adhesion and anti-inflammatory effects of F-HA were examined in chickens at 2, 4, and 8 weeks postoperation. It was concluded that F-HA combined with ibuprofen is a suitable anti-adhesion and anti-inflammation agent.

Keywords:Furfuryl hyaluronic acid;Ibuprofen;Photo-immobilization;Riboflavin;Anti-adhesion;Anti-inflammation

[References]

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[1] Wong YK, Lui YH, Kapacee Z, Kadler KE, Ferguson MW, McGrouther DA, Am. J. Pathol., 175, 1938 (2009)

[2] James R, Kesturu G, Balian G, Chhabra AB, J. Hand Surg. Am., 33, 102 (2008)

[3] Miller JA, Ferguson RL, Powers DL, Burns JW, Shalaby SW, J. Biomed. Mater. Res., 38, 25 (1997)

[4] Bhavsar D, Shettko D, Tenenhaus M, J. Surg. Res., 159, 765 (2010)

[5] Temiz A, Ozturk C, Bakunov A, Kara K, Kaleli T, Int. Orthop., 32, 389 (2008)

[6] Hung LK, Fu SC, Lee YW, Mok TY, Chan KM, J. Bone Joint Surg. Am., 95, e41 (2013)

[7] Hunt J, Flanagan B, McLaughlin P, Strickland I, Williams D, J. Biomed. Mater. Res., 31, 139 (1996)

[8] Tan V, Nourbakhsh A, Capo J, Cottrell JA, Meyenhofer M, O’Connor JP, J. Hand Surg. Am., 35, 941 (2010)

[9] Hellebrekers BW, Trimbos-Kemper TC, Trimbos JBM, Emeis JJ, Kooistra T, Fertil. Steril., 74, 203 (2000)

[10] Harris ES, Morgan RF, Rodeheaver GT, Surgery, 117, 663 (1995)

[11] Bolgen N, Vargel I, Korkusuz P, Menceloglu YZ, Piskin E, J. Biomed. Mater. Res. B Appl. Biomater., 81, 530 (2007)

[12] Stuhlmeier KM, Li H, Kao JJ, Biochem. Pharmacol., 57, 313 (1999)

[13] Ko YG, Yoon KH, Park C, Sung MH, Kwon OK, Ahn CH, Kim YJ, Kwon OH, Key Eng. Mater., 342-343, 225 (2007)

[14] Ito T, Fraser IP, Yeo Y, Highley CB, Bellas E, Kohane DS, Biomaterials, 28, 1778 (2007)

[15] Lee JH, Go AK, Oh SH, Lee KE, Yuk SH, Biomaterials, 26, 671 (2005)

[16] Frijns CJM, Kappelle LJ, Stroke, 33, 2115 (2002)

[17] Hu C, Liu S, Zhang Y, Li B, Yang H, Fan C, Cui W, Acta Biomater., 9, 7381 (2013)

[18] Rossi S, Marciello M, Sandri G, Ferrari F, Bonferoni MC, Papetti A, Caramella C, Dacarro C, Grisoli P, Pharm. Dev. Technol., 12, 415 (2007)

[19] Voigt J, Driver VR, Wound Repair Regen., 20, 317 (2012)

[20] Li L, Wang N, Jin X, Deng R, Nie S, Sun L, Wu Q, Wei Y, Gong C, Biomaterials, 35, 3903 (2014)

[21] Wang D, Dong H, Li M, Meng X, Cao Y, Zhang K, Dai W, Wang C, Zhang X, ACS Sustainable Chem. Eng., 5, 6786 (2017)

[22] Lu C, Han Z, Liu G, Cai X, Chen Y, Yao S, Sci. China. Series B: Chem, 44, 39 (2001)

[23] Encinas MV, Rufs AM, Bertolotti S, Previtali CM, Macromolecules, 34(9), 2845 (2001)

[24] Kim SH, Chu CC, Fibers Polym., 10, 14 (2009)

[25] Park H, Choi B, Hu J, Lee M, Acta Biomater., 9, 4779 (2013)

[26] Burget D, Fouassier J, Amat-Guerri F, Mallavia R, Sastre R, Acta Polym., 50, 337 (1999)

[27] Ibusuki S, Halbesma GJ, Randolph MA, Redmond RW, Kochevar IE, Gill TJ, Tissue Eng., 13, 1995 (2007)

[28] Heo Y, Lee HJ, Kim EH, Kim MK, Ito Y, Son TI, J. Appl. Poly. Sci., 131 (2014)

[29] Park SH, Kim EH, Lee HJ, Heo Y, Cho YM, Seo SY, Kim TY, Suh HW, Kim MK, Ito Y, Nah JW, Son TI, Macromol. Res., 24(4), 336 (2016)

[30] Shi R, Xue J, Wang H, Wang R, Gong M, Chen D, Zhang L, Tian W, J. Mater. Chem. B, 3, 4063 (2015)

[31] Xu L, Cao D, Liu W, Zhou G, Zhang WJ, Cao Y, Biomaterials, 31, 3894 (2010)

[32] Karakurum G, Buyukbebeci O, Kalender M, Gulec A, J. Surg. Res., 113, 195 (2003)

[33] Isık S, Ozturk S, Gurses S, Yetmez M, Guler M, Selmanpakoglu N, Gunhan O, Br. J. Plast. Surg., 52, 373 (1999)

[34] Kim HM, Nelson G, Thomopoulos S, Silva MJ, Das R, Gelberman RH, J. Hand Surg. Am., 35, 1031 (2010)

[35] Son TI, Sakuragi M, Takahashi S, Obuse S, Kang J, Fujishiro M, Matsushita H, Gong J, Shimizu S, Tajima Y, Yoshida Y, Suzuki K, Yamamoto T, Nakamura M, Ito Y, Acta Biomater., 6, 4005 (2010)

[36] Park S, Seo S, Na H, Kim K, Lee J, Woo H, Lee J, Seok H, Lee J, Chung S, Chung KH, Han DK, Ito Y, Jang E, Son T, Macromol. Res., 19(9), 921 (2011)

[37] Liu S, Hu C, Li F, Li XJ, Cui W, Fan C, Tissue Eng. Part A, 19, 529 (2013)

[38] Kuo SM, Chang SJ, Wang HY, Tang SC, Yang SW, Carbohydr. Polym., 114, 230 (2014)