氧化多糖的研究进展
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摘要
通过将多糖的大量羟基氧化为醛基或羧基,可以在保持多糖原有优良性能的同时赋予其理想的化学性,应用于胶原基生物材料的交联。文章总结了氧化多糖的制备、交联胶原的条件、交联产物的性能及其应用等方面的进展,并提出了未来的研究方向。
引文
[1] Liu J, Willf觟r S, Xu CL. A review of bioactive plant polysaccharides:Biological activities, functionalization, and biomedical applications[J]. Bioactive Carbohydrates and Dietary Fibre, 2015, 5(1):31-61.
[2] D’Ayala GG, Malinconico M, Laurienzo P. Marine derived polysaccharides for biomedical applications:chemical modification approaches[J]. Molecules, 2008, 13(9):2069-2106.
[3] ZI Ya-xin, LEI Jin-feng, XU Zhi-lang, et al. Preparation and biomedical applications of oxidized polysaccharides[J].Chinese Journal of Bioprocess Engineering, 2018, 16(1):31-37.[訾娅鑫,雷金凤,徐志朗,等.多糖的氧化改性及在生物医药领域的应用[J].生物加工过程,2018,16(1):31-37.]
[4] Kristiansen KA, Potthast A, Christensen BE. Periodate oxidation of polysaccharides for modification of chemical and physical properties[J]. Carbohydr Res, 2010, 345(10):1264-1271.
[5] Guo J, Ge L, Li X, et al. Periodate oxidation of xanthan gum and its crosslinking effects on gelatin-based edible films[J].Food Hydrocolloids, 2014, 39:243-250.
[6] HE Li-rong, LI Hong-li, ZHANG Kai, et al. Preparation of dialdehyde starch and its enhancement of thermal stability of collagen[J]. China Leather, 2009, 38(15):23-27.[贺丽蓉,李宏利,张凯,等.双醛淀粉的制备及其提高胶原的热稳定性研究[J].中国皮革,2009,38(15):23-27.]
[7] Tan H, Wu B, Li C, et al. Collagen cryogel cross-linked by naturally derived dialdehyde carboxymethyl cellulose[J]. Carbohydr Polym, 2015, 129:17-24.
[8] ZHANG Li-ming, LI Zheng-jun, ZHANG Xiao-bian, et al.Effect of reaction conditions on aldehyde content of dialdehyde yam starch[J]. Modern Food Science&Technology,2013, 29(5):1019-1022.[张黎明,李正君,张晓变,等.反应条件对双醛山药淀粉醛基含量的影响[J].现代食品科技,2013,29(5):1019-1022.]
[9] ZHU Ying, LIU Wen-jie, ZUO Ying-feng, et al. Process optimization of dialdehyde starch prepared by acid hydrolysis and oxidation[J]. Journal of Southwest Forestry University:Natural Science, 2017, 37(3):199-203.[朱颖,刘文杰,左迎峰,等.双醛淀粉酸解氧化制备工艺优化研究[J].西南林业大学学报:自然科学,2017,37(3):199-203.]
[10] CHEN Yi-ning, DAN Nian-hua, WANG Lei, et al. Study on poricine acellular dermal amtrix crosslinked by isomaltooligosaccharide dialdehyde[J]. Journal of Functional Materials, 2016, 47(5):5195-5200.[陈一宁,但年华,王磊,等.双醛低聚异麦芽糖交联脱细胞猪真皮基质的研究[J].功能材料,2016,47(5):5195-5200.]
[11] LüYong, SONG Ci, DAI Lei, et al. Preparation of oxidized chitosan and its application in synthesis and stabilization of silver nanoparticles[J]. Journal of Functional Materials, 2014,45(6):6092-6096, 6101-6101.[吕勇,宋词,戴磊,等.壳聚糖氧化改性及还原稳定纳米银研究[J].功能材料,2014,45(6):6092-6096,6101-6101.]
[12] CHEN Yi-ning. Study on functional glycosylated acellular porcine dermal matrix[D]. Chengdu:Sichuan University, 2017.[陈一宁.功能型糖基化脱细胞猪真皮基质的研究[D].成都:四川大学,2017.]
[13] LI Li, XU Yuan-ting, CHEN Jian, et al. Study on preparation of acellular matrix materials fixed by oxidized sodium alginate and its cytocompatibility[J]. Journal of Biomedical Engineering, 2011, 28(6):1154-1158.[李莉,徐源廷,陈健,等.氧化海藻酸钠交联改性脱细胞基质材料及其细胞相容性研究[J].生物医学工程学杂志,2011,28(6):1154-1158.]
[14] WANG Ya-juan, JIANG Lan, YUAN Bing, et al. Research on properties of oxidized chitin-gelatin films[J]. China Leather,2012, 41(13):12-16.[王亚娟,蒋岚,袁冰,等.氧化壳聚糖/明胶共混膜的制备及性能研究[J].中国皮革,2012,41(13):12-16.]
[15] CHENG Qing-su, WANG Shuo, LI Qiu-hong, et al. Research on properties of dialdehyde starch-collagen films[J].Leather Science and Engineering, 2010, 20(6):8-12, 16-16.[程庆甦,王硕,李秋鸿,等.双醛淀粉/胶原共混膜的制备及性能研究[J].皮革科学与工程,2010,20(6):8-12,16-16.]
[16] LIU Yun, ZHANG Chuan, ZHANG Chuan-jie, et al. The effect of oxidation degrec of oxidized starch on the properties of sodium alginate/gelatin IPNs crosslinked with oxidized starch[J]. Acta Polymerica Sinica, 2015,(4):374-381.[刘云,张川,张传杰,等.氧化淀粉的氧化度对其交联海藻酸钠/明胶互穿网络膜性能的影响[J].高分子学报,2015,(4):374-381.]
[17] XU Yuan-ting, GU Zhi-peng, HUANG Jing-yun, et al. Experimental study of fixing biological tissues for biomaterials by oxidized sodium alginate[J]. Journal of Functional Material, 2010, 41(10):1687-1690.[徐源廷,顾志鹏,黄晶芸,等.氧化海藻酸钠交联生物性组织制备生物材料的实验研究[J].功能材料,2010,41(10):1687-1690.]
[18] Balakrishnan B, Jayakrishnan A. Self-cross-linking biopolymers as injectable in situ forming biodegradable scaffolds[J].Biomaterials, 2005, 26(18):3941-3951.
[19] Draye JP, Delaey B, Van de Voorde A, et al. In vitro and in vivo biocompatibility of dextran dialdehyde cross-linked gelatin hydrogel films[J]. Biomaterials, 1998, 19(18):1677-1687.
[20] YOU Wei-ting, DAN Wei-hua, DAN Nian-hua, et al.Structure and degradation property of collagen film modified by oxidation sodium alginate[J]. China Leather, 2017, 46(8):19-24.[尤伟婷,但卫华,但年华,等.氧化海藻酸钠改性胶原膜的结构及其降解性能[J].中国皮革,2017,46(8):19-24.]
[21] LIANG Ye, LIU Wan-shun, HAN Bao-qin, et al. Preparation and characterization of a novel biodegradable crosslinker[J].Journal of Ocean University of China:Natural Science Edition, 2008, 38(4):590-594.[梁晔,刘万顺,韩宝芹,等.一种新型生物交联剂的制备及其性质[J].中国海洋大学学报:自然科学版,2008,38(4):590-594.]
[22] Yu H, Xiao C. Synthesis and properties of novel hydrogels from oxidized konjac glucomannan crosslinked gelatin for in vitro drug delivery[J]. Carbohydrate Polymers, 2007, 72(3):479-489.
[23] ZHANG Xia, ZHOU Hao, YANG Yu-hong, et al. Oxidized cellulose enhanced collagen hydrogels[J]? Chemical Journal of Chinese Universities, 2015, 36(10):2040-2046.[张霞,周浩,杨宇红,等.氧化纤维素增强胶原水凝胶[J].高等学校化学学报,2015,36(10):2040-2046.]
[24] LU Jin-ting, CHENG Yong-mei, ZHAO Peng, et al. The preparation of regenerated cellulose/collagen composite wound dressing and its performance evaluation[J]. Journal of Functional Materials, 2014, 45(14):14150-14155.[陆金婷,程咏梅,赵朋,等.再生纤维素/胶原蛋白复合伤口敷料的制备及其性能评价[J].功能材料,2014,45(14):14150-14155.]
[25] ZHENG Xue-jing, LI Jun-wei, LIU Jie, et al. Preparation and properties of dialdehyde starch modified gelatin films[J].China Leather, 2011, 40(23):28-31, 36-36.[郑学晶,李俊伟,刘捷,等.双醛淀粉改性明胶膜的制备与性能研究[J].中国皮革,2011,40(23):28-31,36-36.]
[26] Chetouani A, Elkolli M, Bounekhel M, et al. Synthesis and properties of novel hydrogels from oxidized pectin crosslinked gelatin for biomedical applications[J]. Polymer Bulletin, 2014,71(9):2303-2316.
[27] Li D, Ye Y, Li D, et al. Biological properties of dialdehyde carboxymethyl cellulose crosslinked gelatin-PEG composite hydrogel fibers for wound dressings[J]. Carbohydr Polym, 2016,137:508-514.
[28] Mu C, Liu F, Cheng Q, et al. Collagen cryogel cross-linked by dialdehyde starch[J]. Macromolecular Materials and Engineering, 2010, 295(2):100-107.
[29] Balakrishnan B, Mohanty M, Fernandez AC, et al. Evaluation of the effect of incorporation of dibutyryl cyclic adenosine monophosphate in an in situ-forming hydrogel wound dressing based on oxidized alginate and gelatin[J]. Biomaterials,2006, 27(8):1355-1361.
[30] Dawlee S, Sugandhi A, Balakrishnan B, et al. Oxidized chondroitin sulfate-cross-linked gelatin matrixes:a new class of hydrogels[J]. Biomacromolecules, 2005, 6(4):2040-2048.
[31] YAN Xiao-li, FENG Yu-jie, LU Wei, et al. The preparation and characterization of collagen-oxygenatcd hyaluronic acid composite hydrogel scaffold[J]. China Practical Medicine, 2011,6(29):3-5.[岩晓丽,冯玉杰,卢伟,等.胶原/氧化透明质酸复合水凝胶支架的制备与表征[J].中国实用医药,2011,6(29):3-5.]
[32] WANG Lei, DAN Nian-hua, CHEN Yi-ning, et al. Evaluation of chemical cross-linking method of porcine acellular dermal matrix with oxidative chitosam oligosaccharide[J].Biomedical Engineering and Clinical Medicine, 2016, 20(5):443-449.[王磊,但年华,陈一宁,等.氧化壳寡糖交联脱细胞猪真皮基质的研究[J].生物医学工程与临床,2016,20(5):443-449.]
[33] DING Cui-cui, ZHENG Zhi-gong, YANG Jia-yang, et al.The study on the structure and properties of collagen modified by a hybrid material dialdehyde carboxymethyl chitosan-SiO2[J]. Journal of Fujian University of Technology, 2017,15(6):559-562.[丁翠翠,郑志功,杨加扬,等.双醛羧甲基壳聚糖-SiO2杂化材料改性胶原研究[J].福建工程学院学报,2017,15(6):559-562.]
[34] FENG Yu-jie, LU Wei, YAN Xiao-li, et al. Preparation and characterization of collagen/dialdehyde pullulan complex scaffold materials[J]. China Foreign Medical Treatment, 2010,29(21):10-12.[冯玉杰,卢伟,岩小丽,等.双醛普鲁兰改性胶原支架材料的制备与表征[J].中外医疗,2010,29(21):10-12.]
[35] Guo J, Ge L, Li X, et al. Periodate oxidation of xanthan gum and its crosslinking effects on gelatin-based edible films[J].Food Hydrocolloids, 2014, 39:243-250.
[36] Thi TTH, Lee Y, Ryu SB, et al. Oxidized cyclodextrin-functionalized injectable gelatin hydrogels as a new platform for tissue-adhesive hydrophobic drug delivery[J]. Rsc Advances,2017, 7(54):34053-34062.
[2] D’Ayala GG, Malinconico M, Laurienzo P. Marine derived polysaccharides for biomedical applications:chemical modification approaches[J]. Molecules, 2008, 13(9):2069-2106.
[3] ZI Ya-xin, LEI Jin-feng, XU Zhi-lang, et al. Preparation and biomedical applications of oxidized polysaccharides[J].Chinese Journal of Bioprocess Engineering, 2018, 16(1):31-37.[訾娅鑫,雷金凤,徐志朗,等.多糖的氧化改性及在生物医药领域的应用[J].生物加工过程,2018,16(1):31-37.]
[4] Kristiansen KA, Potthast A, Christensen BE. Periodate oxidation of polysaccharides for modification of chemical and physical properties[J]. Carbohydr Res, 2010, 345(10):1264-1271.
[5] Guo J, Ge L, Li X, et al. Periodate oxidation of xanthan gum and its crosslinking effects on gelatin-based edible films[J].Food Hydrocolloids, 2014, 39:243-250.
[6] HE Li-rong, LI Hong-li, ZHANG Kai, et al. Preparation of dialdehyde starch and its enhancement of thermal stability of collagen[J]. China Leather, 2009, 38(15):23-27.[贺丽蓉,李宏利,张凯,等.双醛淀粉的制备及其提高胶原的热稳定性研究[J].中国皮革,2009,38(15):23-27.]
[7] Tan H, Wu B, Li C, et al. Collagen cryogel cross-linked by naturally derived dialdehyde carboxymethyl cellulose[J]. Carbohydr Polym, 2015, 129:17-24.
[8] ZHANG Li-ming, LI Zheng-jun, ZHANG Xiao-bian, et al.Effect of reaction conditions on aldehyde content of dialdehyde yam starch[J]. Modern Food Science&Technology,2013, 29(5):1019-1022.[张黎明,李正君,张晓变,等.反应条件对双醛山药淀粉醛基含量的影响[J].现代食品科技,2013,29(5):1019-1022.]
[9] ZHU Ying, LIU Wen-jie, ZUO Ying-feng, et al. Process optimization of dialdehyde starch prepared by acid hydrolysis and oxidation[J]. Journal of Southwest Forestry University:Natural Science, 2017, 37(3):199-203.[朱颖,刘文杰,左迎峰,等.双醛淀粉酸解氧化制备工艺优化研究[J].西南林业大学学报:自然科学,2017,37(3):199-203.]
[10] CHEN Yi-ning, DAN Nian-hua, WANG Lei, et al. Study on poricine acellular dermal amtrix crosslinked by isomaltooligosaccharide dialdehyde[J]. Journal of Functional Materials, 2016, 47(5):5195-5200.[陈一宁,但年华,王磊,等.双醛低聚异麦芽糖交联脱细胞猪真皮基质的研究[J].功能材料,2016,47(5):5195-5200.]
[11] LüYong, SONG Ci, DAI Lei, et al. Preparation of oxidized chitosan and its application in synthesis and stabilization of silver nanoparticles[J]. Journal of Functional Materials, 2014,45(6):6092-6096, 6101-6101.[吕勇,宋词,戴磊,等.壳聚糖氧化改性及还原稳定纳米银研究[J].功能材料,2014,45(6):6092-6096,6101-6101.]
[12] CHEN Yi-ning. Study on functional glycosylated acellular porcine dermal matrix[D]. Chengdu:Sichuan University, 2017.[陈一宁.功能型糖基化脱细胞猪真皮基质的研究[D].成都:四川大学,2017.]
[13] LI Li, XU Yuan-ting, CHEN Jian, et al. Study on preparation of acellular matrix materials fixed by oxidized sodium alginate and its cytocompatibility[J]. Journal of Biomedical Engineering, 2011, 28(6):1154-1158.[李莉,徐源廷,陈健,等.氧化海藻酸钠交联改性脱细胞基质材料及其细胞相容性研究[J].生物医学工程学杂志,2011,28(6):1154-1158.]
[14] WANG Ya-juan, JIANG Lan, YUAN Bing, et al. Research on properties of oxidized chitin-gelatin films[J]. China Leather,2012, 41(13):12-16.[王亚娟,蒋岚,袁冰,等.氧化壳聚糖/明胶共混膜的制备及性能研究[J].中国皮革,2012,41(13):12-16.]
[15] CHENG Qing-su, WANG Shuo, LI Qiu-hong, et al. Research on properties of dialdehyde starch-collagen films[J].Leather Science and Engineering, 2010, 20(6):8-12, 16-16.[程庆甦,王硕,李秋鸿,等.双醛淀粉/胶原共混膜的制备及性能研究[J].皮革科学与工程,2010,20(6):8-12,16-16.]
[16] LIU Yun, ZHANG Chuan, ZHANG Chuan-jie, et al. The effect of oxidation degrec of oxidized starch on the properties of sodium alginate/gelatin IPNs crosslinked with oxidized starch[J]. Acta Polymerica Sinica, 2015,(4):374-381.[刘云,张川,张传杰,等.氧化淀粉的氧化度对其交联海藻酸钠/明胶互穿网络膜性能的影响[J].高分子学报,2015,(4):374-381.]
[17] XU Yuan-ting, GU Zhi-peng, HUANG Jing-yun, et al. Experimental study of fixing biological tissues for biomaterials by oxidized sodium alginate[J]. Journal of Functional Material, 2010, 41(10):1687-1690.[徐源廷,顾志鹏,黄晶芸,等.氧化海藻酸钠交联生物性组织制备生物材料的实验研究[J].功能材料,2010,41(10):1687-1690.]
[18] Balakrishnan B, Jayakrishnan A. Self-cross-linking biopolymers as injectable in situ forming biodegradable scaffolds[J].Biomaterials, 2005, 26(18):3941-3951.
[19] Draye JP, Delaey B, Van de Voorde A, et al. In vitro and in vivo biocompatibility of dextran dialdehyde cross-linked gelatin hydrogel films[J]. Biomaterials, 1998, 19(18):1677-1687.
[20] YOU Wei-ting, DAN Wei-hua, DAN Nian-hua, et al.Structure and degradation property of collagen film modified by oxidation sodium alginate[J]. China Leather, 2017, 46(8):19-24.[尤伟婷,但卫华,但年华,等.氧化海藻酸钠改性胶原膜的结构及其降解性能[J].中国皮革,2017,46(8):19-24.]
[21] LIANG Ye, LIU Wan-shun, HAN Bao-qin, et al. Preparation and characterization of a novel biodegradable crosslinker[J].Journal of Ocean University of China:Natural Science Edition, 2008, 38(4):590-594.[梁晔,刘万顺,韩宝芹,等.一种新型生物交联剂的制备及其性质[J].中国海洋大学学报:自然科学版,2008,38(4):590-594.]
[22] Yu H, Xiao C. Synthesis and properties of novel hydrogels from oxidized konjac glucomannan crosslinked gelatin for in vitro drug delivery[J]. Carbohydrate Polymers, 2007, 72(3):479-489.
[23] ZHANG Xia, ZHOU Hao, YANG Yu-hong, et al. Oxidized cellulose enhanced collagen hydrogels[J]? Chemical Journal of Chinese Universities, 2015, 36(10):2040-2046.[张霞,周浩,杨宇红,等.氧化纤维素增强胶原水凝胶[J].高等学校化学学报,2015,36(10):2040-2046.]
[24] LU Jin-ting, CHENG Yong-mei, ZHAO Peng, et al. The preparation of regenerated cellulose/collagen composite wound dressing and its performance evaluation[J]. Journal of Functional Materials, 2014, 45(14):14150-14155.[陆金婷,程咏梅,赵朋,等.再生纤维素/胶原蛋白复合伤口敷料的制备及其性能评价[J].功能材料,2014,45(14):14150-14155.]
[25] ZHENG Xue-jing, LI Jun-wei, LIU Jie, et al. Preparation and properties of dialdehyde starch modified gelatin films[J].China Leather, 2011, 40(23):28-31, 36-36.[郑学晶,李俊伟,刘捷,等.双醛淀粉改性明胶膜的制备与性能研究[J].中国皮革,2011,40(23):28-31,36-36.]
[26] Chetouani A, Elkolli M, Bounekhel M, et al. Synthesis and properties of novel hydrogels from oxidized pectin crosslinked gelatin for biomedical applications[J]. Polymer Bulletin, 2014,71(9):2303-2316.
[27] Li D, Ye Y, Li D, et al. Biological properties of dialdehyde carboxymethyl cellulose crosslinked gelatin-PEG composite hydrogel fibers for wound dressings[J]. Carbohydr Polym, 2016,137:508-514.
[28] Mu C, Liu F, Cheng Q, et al. Collagen cryogel cross-linked by dialdehyde starch[J]. Macromolecular Materials and Engineering, 2010, 295(2):100-107.
[29] Balakrishnan B, Mohanty M, Fernandez AC, et al. Evaluation of the effect of incorporation of dibutyryl cyclic adenosine monophosphate in an in situ-forming hydrogel wound dressing based on oxidized alginate and gelatin[J]. Biomaterials,2006, 27(8):1355-1361.
[30] Dawlee S, Sugandhi A, Balakrishnan B, et al. Oxidized chondroitin sulfate-cross-linked gelatin matrixes:a new class of hydrogels[J]. Biomacromolecules, 2005, 6(4):2040-2048.
[31] YAN Xiao-li, FENG Yu-jie, LU Wei, et al. The preparation and characterization of collagen-oxygenatcd hyaluronic acid composite hydrogel scaffold[J]. China Practical Medicine, 2011,6(29):3-5.[岩晓丽,冯玉杰,卢伟,等.胶原/氧化透明质酸复合水凝胶支架的制备与表征[J].中国实用医药,2011,6(29):3-5.]
[32] WANG Lei, DAN Nian-hua, CHEN Yi-ning, et al. Evaluation of chemical cross-linking method of porcine acellular dermal matrix with oxidative chitosam oligosaccharide[J].Biomedical Engineering and Clinical Medicine, 2016, 20(5):443-449.[王磊,但年华,陈一宁,等.氧化壳寡糖交联脱细胞猪真皮基质的研究[J].生物医学工程与临床,2016,20(5):443-449.]
[33] DING Cui-cui, ZHENG Zhi-gong, YANG Jia-yang, et al.The study on the structure and properties of collagen modified by a hybrid material dialdehyde carboxymethyl chitosan-SiO2[J]. Journal of Fujian University of Technology, 2017,15(6):559-562.[丁翠翠,郑志功,杨加扬,等.双醛羧甲基壳聚糖-SiO2杂化材料改性胶原研究[J].福建工程学院学报,2017,15(6):559-562.]
[34] FENG Yu-jie, LU Wei, YAN Xiao-li, et al. Preparation and characterization of collagen/dialdehyde pullulan complex scaffold materials[J]. China Foreign Medical Treatment, 2010,29(21):10-12.[冯玉杰,卢伟,岩小丽,等.双醛普鲁兰改性胶原支架材料的制备与表征[J].中外医疗,2010,29(21):10-12.]
[35] Guo J, Ge L, Li X, et al. Periodate oxidation of xanthan gum and its crosslinking effects on gelatin-based edible films[J].Food Hydrocolloids, 2014, 39:243-250.
[36] Thi TTH, Lee Y, Ryu SB, et al. Oxidized cyclodextrin-functionalized injectable gelatin hydrogels as a new platform for tissue-adhesive hydrophobic drug delivery[J]. Rsc Advances,2017, 7(54):34053-34062.