含腙键透明质酸-右旋糖酐嵌段聚合物的合成

doi:10.3969/j.issn.1000-1565.2019.05.007

河北大学学报(自然科学版) ›› 2019, Vol. 39 ›› Issue (5): 484-490.DOI: 10.3969/j.issn.1000-1565.2019.05.007

含腙键透明质酸-右旋糖酐嵌段聚合物的合成

刘浩帆^1,2,李心^1,2,胡连栋^1,2

收稿日期:2018-08-20 出版日期:2019-09-25 发布日期:2019-09-25
通讯作者: 胡连栋(1978—),男,河北石家庄人,河北大学教授,博士,主要从事药物新制剂研究.E-mail:hbupharm@126.com
作者简介:刘浩帆(1994—),男,河北石家庄人,河北大学在读硕士研究生. E-mail:491384677@qq.com 〓通信作者:胡连栋(1978—),男,河北石家庄人,河北大学教授,博士,主要从事药物新制剂研究. E-mail:hbupharm@126.com
基金资助:
河北省首批青年拔尖人才项目;河北省高等学校科学研究项目(ZD2016136)

Synthesis of hyaluronic acid-dextran block polymers containing hydrazone

LIU Haofan^1,2, LI Xin^1,2,HU Liandong^1,2

1. College of Pharmaceutical Science, Hebei University, Baoding 071002, China; 2. Key Laboratory of Pharmaceutical Quality Control of Hebei Province, Baoding 071002, China

Received:2018-08-20 Online:2019-09-25 Published:2019-09-25

摘要/Abstract

摘要： 采用生物可降解、无毒性的透明质酸以及右旋糖酐40等原料分别合成透明质酸酰肼(HA-NHNH₂)与氧化右旋糖酐40(Odex 40),并通过氧化度测定,确定了合成Odex 40的最优方法.将上述2种物质进行反应,合成得到含腙键的透明质酸-氧化右旋糖酐嵌段聚合物(HA-Hz-Odex).通过核磁共振波谱实验表明成功合成了含腙键的嵌段聚合物HA-Hz-Odex.

关键词: 透明质酸, 右旋糖酐, 腙键, 嵌段聚合物

Abstract: Hyaluronic acid hydrazide(HA-NHNH₂)and oxidized dextran 40(Odex 40)were synthesized by using biodegradable and non-toxic hyaluronic acid and dextran 40. The optimum method for the synthesis of oxidized dextran 40 was determined by oxidation degree. The above two substances were reacted with each other to obtain a hyaluronic acid-oxidized dextran block copolymer(HA-Hz-Odex)containing a hydrazine bond. The NMR study shows that the HA-Hz-Odex block copolymers containing hydrazine bonds have been successfully synthesized.

Key words: hyaluronic acid, dextran, hydrazone, block polymer

中图分类号:

O621.3

刘浩帆,李心,胡连栋. 含腙键透明质酸-右旋糖酐嵌段聚合物的合成[J]. 河北大学学报(自然科学版), 2019, 39(5): 484-490.

LIU Haofan, LI Xin,HU Liandong. Synthesis of hyaluronic acid-dextran block polymers containing hydrazone[J]. Journal of Hebei University (Natural Science Edition), 2019, 39(5): 484-490.

参考文献

[1] KOST J, LANGER R. Responsive polymeric delivery systems[J]. Advanced Drug Delivery Reviews, 2012, 6(1-3):125-148. DOI:10.1016/j.addr.2012.09.014.
[2] TAMAR T, RIKI G, JOSEPH K. Smart polymers for responsive drug-delivery systems[J]. Journal of Biomaterials Science Polymer Edition, 2008, 19(6):755-767. DOI:10.1163/156856208784522065.
[3] GILLIES E R, GOODWIN A P, FRECHET J M. Acetals as pH-sensitive linkages for drug delivery[J]. Bioconjugate Chemistry, 2004, 15(6):1254-1263. DOI:10.1021/bc049853x.
[4] RADOVIC-MORENO A F, LU T K, Puscasu V A, et al. Surface charge-switching polymeric nanoparticles for bacterial cell wall-targeted delivery of antibiotics[J]. Acs Nano, 2012, 6(5):4279-87. DOI:10.1021/nn3008383.
[5] YU J, ZHANG Y, BOMBA H, et al. Stimuli-responsive delivery of therapeutics for diabetes treatment[J]. Bioengineering & Translational Medicine, 2016,1(3):323. DOI:10.1002/btm2.10036.
[6] TAGHIZADEH B, TARANEJOO S, MONEMIAN SA, et al. Classification of stimuli-responsive polymers as anticancer drug delivery systems[J]. Drug Delivery, 2015, 22(2):145-155. DOI:10.3109/10717544.2014.887157.
[7] YONCHEVA K, PETROV P, PENCHEVA I,et al. Triblock polymeric micelles as carriers for anti-inflammatory drug delivery[J]. Journal of Microencapsulation, 2015, 32(3):224-230. DOI:10.3109/02652048.2014.995729.
[8] PATIL B R, MACHAKANUR S S, HUNOOR R S, et al. Synthesis and anti-cancer evaluation of cyclotriphosphazene hydrazone derivatives[J]. Der Pharma Chemica, 2011, 3(4):377-388.
[9] 李记太,张冬暖,宋亚丽. 微波辐射一锅法合成N-(4-芳基噻唑-2-基)-腙类化合物[J]. 河北大学学报(自然科学版),2012,32(3):261-264. DOI:10.3969/j.issn.1000-1565.2012.03.008.
[10] SU X, APRAHAMIAN I. Hydrazone-based switches, metallo-assemblies and sensors[J]. Chemical Society Reviews, 2014, 43(6):1963-1981. DOI:10.1039/c3cs60385g.
[11] YOSHIDA T, LAI T C, KWON G S, et al. pH- and ion-sensitive polymers for drug delivery[J]. Expert Opinion on Drug Delivery, 2013, 10(11):1497. DOI:10.1517/17425247.2013.821978.
[12] LI C, LIH, WANG Q, et al. pH-sensitive polymeric micelles for targeted delivery to inflamed joints[J]. Journal of Controlled Release, 2017, 246:133-141. DOI:10.1016/j.jconrel.2016.12.027.
[13] SONAWANE S J, KALHAPURE R S, GOVENDER T. Hydrazone linkages in pH responsive drug delivery systems[J]. European Journal of Pharmaceutical Sciences, 2017, 99:45-65. DOI:10.1016/j.ejps.2016.12.011.
[14] DING Y, SUN D, WANG G L,et al. An efficient PEGylated liposomal nanocarrier containing cell-penetrating peptide and pH-sensitive hydrazone bond for enhancing tumor-targeted drug delivery[J]. International Journal of Nanomedicine, 2015, 10:6199-6214. DOI:10.2147/ijn.s92519.
[15] BULPITT P, AESCHLIMANN D. New strategy for chemical modification of hyaluronic acid: Preparation of functionalized derivatives and their use in the formation of novel biocompatible hydrogels[J]. Journal of Biomedical Materials Research Part A,1999,47(2):152-169.
[16] 张莉,刘哲鹏,陆伟跃,等. 氧化葡聚糖交联明胶微球的制备及性质[J]. 中国医药工业杂志, 2003, 34(5):230-232.
[17] HUDSON S P, LANGER R, FINK G R, et al. Injectable in situ cross-linking hydrogels for local antifungal therapy[J]. Biomaterials, 2010, 31(6):1444-1452. DOI:10.1016/j.biomaterials.2009.11.016.

含腙键透明质酸-右旋糖酐嵌段聚合物的合成

Synthesis of hyaluronic acid-dextran block polymers containing hydrazone

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