METHOD OF RESIDUE ASSAY OF CROSSLINKING AGENT IN CROSS-LINKED SODIUM HYALURONIC GEL_Chinese Journal of Reparative and Reconstructive Surgery

Authors：

 WEIChangzheng , LÜHuanghong , ZHANGJian , ZHUBin , JIANGLixia

Shanghai Qisheng Biological Preparation Co., LTD, Shanghai, 201106, P. R. China;

Corresponding author：

WEIChangzheng, Email: czwei@3healthcare.com

Keywords：

Cross-linked sodium hyaluronic; 1,4-butanediol diglycidyl ether; Residue; Fluorescence spectrophotometry; Crosslinking agent

DOI：

10.7507/1002-1892.20150132

Video：

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Objective To establish a more accurately method to detect the residue of 1,4-butanediol diglycidyl-ether (BDDE) in the cross-linked sodium hyaluronic gel so as to provide a scientific testing method for the quality control. Methods The gas chromatography was used to explore the thermal stability of BDDE, and the residues of BDDE in sodium hyaluronic gel was detected by fluorescence spectrophotometry. The hyaluronidase was added to the BDDE standard solution and the improved fluorescence spectrophotometer was used to detect the BDDE residues in the cross-linked hyaluronic sodium gel. Results A good linearity was obtained as y=14.102x+1.103 (R²=0.999 8) for BDDE. BDDE was unstable under high temperature and long storage time. The relevant fluorescence intensity was detected with hyaluronidase solution. After adding hyaluronidase into the BDDE standard solutions, the advanced linearity was obtained as y=14.027x+7.062 (R²=0.999 9). Conclusion Fluorescent spectrophotometry is a simple, rapid, and accurate method to analyze BDDE residue of cross-linked sodium hyaluronic gel. Due to the poor thermal stability, all the factors related to temperature must be excluded during the process, including the temperature control of every step. Furthermore, the adding of hyaluronidase in the pre-preparation of cross-linked sodium hyaluronic gel can bring interference. So when using fluorescent spectrophotometry, adjustment must be taken before the calibration curve is preparation.

Citation： WEIChangzheng, LÜHuanghong, ZHANGJian, ZHUBin, JIANGLixia. METHOD OF RESIDUE ASSAY OF CROSSLINKING AGENT IN CROSS-LINKED SODIUM HYALURONIC GEL. Chinese Journal of Reparative and Reconstructive Surgery, 2015, 29(5): 615-619. doi: 10.7507/1002-1892.20150132 Copy

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2.	Laurent TC, Fraser JR. Hyaluronan. FASEB J, 1992, 6(7):2397-2404.
3.	Xian X, Jha AK, Harrington DA, et al. Hyaluronic acid-based hydrogels:from a natural polysaccharide to complex networks. Soft Matter, 2012, 8(12):3280-3294.
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8.	Tomihata K, Ikada Y. Crosslinking of hyaluronic acid with water-soluble carbodiimide. J Biomed Mater Res, 1997, 37(2):243-251.
9.	米鹏程, 王伯初, 冯薇, 等. 二乙烯基砜交联透明质酸钠凝胶的制备及其生物相容性. 中国组织工程研究与临床康复, 2008, 12(14):2675-2678.
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12.	陈建英, 汪敏, 刘杰,等. 注射用交联透明质酸钠凝胶的制备及其体外抗酶降解性的研究. 中国生化药物杂志, 2008, 29(4):262-265.
13.	De Boulle K, Glogau R, Kono T, et al. A review of the metabolism of 1,4-butanediol diglycidyl ether-crosslinked hyaluronic acid dermal fillers. Dermatol Surg, 2013, 39(12):1758-1766.
14.	Yeom J, Bhang SH, Kim BS, et al. Effect of cross-linking reagents for hyaluronic acid hydrogel dermal fillers on tissue augmentation and regeneration. Bioconjug Chem, 2010, 21(2):240-247.
15.	张健, 奚宏伟, 朱彬,等. 荧光分光光度法检测交联透明质酸中交联剂残留量. 生物医学工程学进展, 2011, 32(4):198-200.
16.	冯海, 张格, 徐玉芸, 等. 荧光分光光度法测定交联透明质酸凝胶中交联剂的残留量. 药物分析杂志, 2013, 32(4):654-657.
17.	唐燕发, 许建和, 叶勤. 分光光度法测定环氧化物浓度与环氧化物水解酶活性. 分析科学学报, 2002, 18(2):142-144.
18.	Lai JY. Relationship between structure and cytocompatibility of divinyl sulfone cross-linked hyaluronic acid. Carbohydr Polym, 2014, 101:203-212.
19.	Ibrahim S, Kang QK, Ramamurthi A. The impact of hyaluronic acid oligomer content on physical, mechanical, and biologic properties of divinyl sulfone-crosslinked hyaluronic acid hydrogels. J Biomed Mater Res A, 2010, 94(2):355-370.
20.	Credi C, Biella S, De Marco C, et al. Fine tuning and measurement of mechanical properties of crosslinked hyaluronic acid hydrogels as biomimetic scaffold coating in regenerative medicine. J Mech Behav Biomed Mater, 2014, 29:309-316.
21.	La Gatta A, Schiraldi C, Papa A, et al. Hyaluronan scaffolds via diglycidyl ether crosslinking:toward improvements in composition and performance. Carbohydr Polym, 2013, 96(2):536-544.

1. Prestwich GD, Marecak DM, MJF, et al. Controlled chemical modification of hyaluronic acid:synthesis, applications, and biodegradation of hydrazide derivatives. J Contr Rel, 1998, 53(1-3):93-103.
2. Laurent TC, Fraser JR. Hyaluronan. FASEB J, 1992, 6(7):2397-2404.
3. Xian X, Jha AK, Harrington DA, et al. Hyaluronic acid-based hydrogels:from a natural polysaccharide to complex networks. Soft Matter, 2012, 8(12):3280-3294.
4. Burdick JA, Presteich GD. Hyaluronic acid hydrogels for biomedical applications. Adv Mat, 2011, 23(12):H41-56.
5. Edsman K, Nord LI, Ohrlund A, et al. Gel properties of hyaluronic acid dermal fillers. Dermatol Surg, 2012, 38(7 Pt 2):1170-1179.
6. Kablik J, Monheit GD, Yu L, et al. Comparative physical properties of hyaluronic acid dermal fillers. Dermatol Surg, 2009, 35 Suppl 1:302-312.
7. Bencherif SA, Srinivasan A, Horkay F, et al. Influence of the degree of methacrylation on hyaluronic acid hydrogels properties. Biomaterials, 2008, 29(12):1739-1749.
8. Tomihata K, Ikada Y. Crosslinking of hyaluronic acid with water-soluble carbodiimide. J Biomed Mater Res, 1997, 37(2):243-251.
9. 米鹏程, 王伯初, 冯薇, 等. 二乙烯基砜交联透明质酸钠凝胶的制备及其生物相容性. 中国组织工程研究与临床康复, 2008, 12(14):2675-2678.
10. Fakharia A, Berkland C. Applications and emerging trends of hyaluronic acid in tissue engineering, as a dermal filler and in osteoarthritis treatment. Acta Biomaterialia, 2013, 9(7):7081-7092.
11. 赵乐军, 白硕佳, 曹红英, 等. 透明质酸钠交联凝胶的制备. 透析与人工器官, 2002, 13(1):45-46.
12. 陈建英, 汪敏, 刘杰,等. 注射用交联透明质酸钠凝胶的制备及其体外抗酶降解性的研究. 中国生化药物杂志, 2008, 29(4):262-265.
13. De Boulle K, Glogau R, Kono T, et al. A review of the metabolism of 1,4-butanediol diglycidyl ether-crosslinked hyaluronic acid dermal fillers. Dermatol Surg, 2013, 39(12):1758-1766.
14. Yeom J, Bhang SH, Kim BS, et al. Effect of cross-linking reagents for hyaluronic acid hydrogel dermal fillers on tissue augmentation and regeneration. Bioconjug Chem, 2010, 21(2):240-247.
15. 张健, 奚宏伟, 朱彬,等. 荧光分光光度法检测交联透明质酸中交联剂残留量. 生物医学工程学进展, 2011, 32(4):198-200.
16. 冯海, 张格, 徐玉芸, 等. 荧光分光光度法测定交联透明质酸凝胶中交联剂的残留量. 药物分析杂志, 2013, 32(4):654-657.
17. 唐燕发, 许建和, 叶勤. 分光光度法测定环氧化物浓度与环氧化物水解酶活性. 分析科学学报, 2002, 18(2):142-144.
18. Lai JY. Relationship between structure and cytocompatibility of divinyl sulfone cross-linked hyaluronic acid. Carbohydr Polym, 2014, 101:203-212.
19. Ibrahim S, Kang QK, Ramamurthi A. The impact of hyaluronic acid oligomer content on physical, mechanical, and biologic properties of divinyl sulfone-crosslinked hyaluronic acid hydrogels. J Biomed Mater Res A, 2010, 94(2):355-370.
20. Credi C, Biella S, De Marco C, et al. Fine tuning and measurement of mechanical properties of crosslinked hyaluronic acid hydrogels as biomimetic scaffold coating in regenerative medicine. J Mech Behav Biomed Mater, 2014, 29:309-316.
21. La Gatta A, Schiraldi C, Papa A, et al. Hyaluronan scaffolds via diglycidyl ether crosslinking:toward improvements in composition and performance. Carbohydr Polym, 2013, 96(2):536-544.

Chinese Journal of Reparative and Reconstructive Surgery

METHOD OF RESIDUE ASSAY OF CROSSLINKING AGENT IN CROSS-LINKED SODIUM HYALURONIC GEL

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