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.
4.	Burdick JA, Presteich GD. Hyaluronic acid hydrogels for biomedical applications. Adv Mat, 2011, 23(12):H41-56.
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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.	米鵬程, 王伯初, 馮薇, 等. 二乙烯基砜交聯透明質酸鈉凝膠的制備及其生物相容性. 中國組織工程研究與臨床康復, 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.	趙樂軍, 白碩佳, 曹紅英, 等. 透明質酸鈉交聯凝膠的制備. 透析與人工器官, 2002, 13(1):45-46.
12.	陳建英, 汪敏, 劉杰,等. 注射用交聯透明質酸鈉凝膠的制備及其體外抗酶降解性的研究. 中國生化藥物雜志, 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.	張健, 奚宏偉, 朱彬,等. 熒光分光光度法檢測交聯透明質酸中交聯劑殘留量. 生物醫學工程學進展, 2011, 32(4):198-200.
16.	馮海, 張格, 徐玉蕓, 等. 熒光分光光度法測定交聯透明質酸凝膠中交聯劑的殘留量. 藥物分析雜志, 2013, 32(4):654-657.
17.	唐燕發, 許建和, 葉勤. 分光光度法測定環氧化物濃度與環氧化物水解酶活性. 分析科學學報, 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. 米鵬程, 王伯初, 馮薇, 等. 二乙烯基砜交聯透明質酸鈉凝膠的制備及其生物相容性. 中國組織工程研究與臨床康復, 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. 趙樂軍, 白碩佳, 曹紅英, 等. 透明質酸鈉交聯凝膠的制備. 透析與人工器官, 2002, 13(1):45-46.
12. 陳建英, 汪敏, 劉杰,等. 注射用交聯透明質酸鈉凝膠的制備及其體外抗酶降解性的研究. 中國生化藥物雜志, 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. 張健, 奚宏偉, 朱彬,等. 熒光分光光度法檢測交聯透明質酸中交聯劑殘留量. 生物醫學工程學進展, 2011, 32(4):198-200.
16. 馮海, 張格, 徐玉蕓, 等. 熒光分光光度法測定交聯透明質酸凝膠中交聯劑的殘留量. 藥物分析雜志, 2013, 32(4):654-657.
17. 唐燕發, 許建和, 葉勤. 分光光度法測定環氧化物濃度與環氧化物水解酶活性. 分析科學學報, 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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