Preparation and characterization of a new hyaluronic acid grafted pullulan material

doi:10.3969/j.issn.1000-1565.2017.02.006

Abstract

Abstract: A series of hyaluronic acid grafted pullulan(HA-Pu)were prepared by esterification reaction,using 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide(EDC)as dehydrating agent and 4-dimethylaminopyridine(DMAP)as catalyst.The structure of HA-Pu was confirmed by the Fourier transform infrared spectrum(FTIR)and proton nuclear magnetic resonance(¹H NMR),and the degree of substitution(DS)of hyaluronic acid moiety was determined by ¹H NMR.The freeze-dried HA-Pu materials could be compressed to obtain a HA-Pu film.The HA-Pu film was observed by scanning electron microscopy(SEM),which obtained the layered microstructure with a lot of small holes.Compared with hyaluronic acid,the HA-Pu materials have better ability to resist enzyme degradation in vitro.Therefore,HA-Pu should be a promising novel material to expand the application of hyaluronic acid in pharmaceatics.

Key words: hyaluronic acid, pullulan, chemical grafting, enzyme degradation in vitro

CLC Number:

O658

YANG Wenzhi,WANG Shugen,LIU Jiaoyan,JIA Bei,LI Haiying. Preparation and characterization of a new hyaluronic acid grafted pullulan material[J]. Journal of Hebei University (Natural Science Edition), 2017, 37(2): 141-146.

References

[1] TEH B M,SHEN Y,FRIEDLAND P L,et al.A review on the use of hyaluronic acid in tympanic membrane wound healing[J].Expert Opinion on Biological Therapy,2012,12(1):23-36.DOI:10.1517/14712598.2012.634792.
[2] CUI N,QIAN J M,XU W J,et al.Preparation characterization and biocompatibility evaluation of poly(Nε-acryloyl-l-lysine)hyaluronic acid interpenetrating network hydrogels[J].Carbohydrate Polymers,2016,136:1017-1026.DOI:10.1016/j.carbpol.2015.09.095.
[3] WANG D H,BIAN J J,WEI G Y,et al.Simultaneously enhanced production and molecular weight of pullulan using a two-stage agitation speed control strategy[J].Journal of Chemical Technology and Biotechnology,2016,91(2):467-475.DOI:10.1002/jctb.4600.
[4] ROGERS Y E,IIO N,TAKEMUR A,et al.Synthesis and characterization of pullulan alkyl esters[J].European Polymer Journal,2015,66:470-477.DOI:10.1016/j.eurpolymj.2015.03.007.
[5] 杨文智,王苗苗,李海鹰,等.生物素化胆甾醇基普鲁兰糖合成及其自聚集性质[J].河北大学学报(自然科学版),2014,34(1):34-39.DOI:10.3969/j.issn.1000-1565.2014.01.007. YANG W Z,WANG M M,LI H Y,et al.Synthesis of biotin modified cholesteryl pullulan and its self-aggregated behavior[J].Journal of Hebei University(Natural Science Edition),2014,34(1):34-39.DOI:10.3969/j.issn.1000-1565.2014.01.007.
[6] BURDICK J A,PRESTWICH G D.Hyaluronic Acid hydrogels for biomedical applications[J].Advanced Materials,2011,23(12):41-56.DOI:10.1002/adma.201003963.
[7] JEON O,SONG S J,LEE K J,et al.Mechanical properties and degradation behaviors of hyaluronic acid hydrogels cross-linked at various cross-linking densities[J].Carbohydrate Polymers,2007,70(3): 251-257.DOI:10.1016/j.carbpol.2007.04.002.
[8] 李贤.普鲁兰多糖-透明质酸水凝胶及其制备方法:中国,CN104861178A[P].2015-05-26.
[9] 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[J].生物学医学工程学进展,2011,3(4):198-200.DOI:10.3969/j.issn.1674-1242.2011.04.005. ZHANG J,XI H W,ZHU B,et al.Fluorescence spectrophotometry detection crosslinking agent residues in crosslinking hyaluronic acid[J].Progress in Biomedical Engineering,2011,3(4):198-200.DOI:10.3969/j.issn.1674-1242.2011.04.005.
[10] MANETA C,IONUT M,IONELA O,et al.Studies on graft copolymerization of 3-acrylamidopropyl trimethylammonium chloride on pullulan[J].Carbohydrate Polymers,2011,84(3):926-932.DOI:10.1016/j.carbpol.2010.12.043.
[11] 孙汉文,许成燕,赵燕燕,等.枸杞多糖硫酸酯化修饰及其对Hela细胞的体外抑制作用[J].河北大学学报(自然科学版),2009,29(6):591-595.DOI:10.3969/j.issn.1000-1565.2009.06.009. SUN H W,XU C Y,ZHAO Y Y,et al.Sulfation for modification of lycium barbarum polysaccharide and its inhibiting effect to growth of hela cell in vitro[J].Journal of Hebei University(Natural Science Edition),2009,29(6):591-595.DOI:10.3969/j.issn.1000-1565.2009.06.009.
[12] SHAH N N,VISHWASRAO C,SINGHAL R S,et al.n-Octenyl succinylation of pullulan:Effect on its physico-mechanical and thermal properties and application as an edible coating on fruits[J].Food Hydrocolloids,2016,55:179-188.DOI:10.1016/j.foodhyd.2015.11.026.
[13] WELTI D,REES D A,WELSH E J,et al.Solution conformation of glycosaminoglycans:assignment of the 300-MHz H-magnetic resonance spectra of chondroitin 4-sulphate,chondroitin 6-sulphate and hyaluronate,and investigation of an alkali-induced conformation change[J].European Journal of Biochemistry,1979,94(2):505-514.DOI:10.1111/j.1432-1033.1979.tb12919.x.
[14] DEANE D M,HANS J V.Structural studies of pullulan by nuclear magnetic resonance spectroscopy[J].Starch-Starke,1993,45(11):406-410.DOI:10.1002/star.19930451108.
[15] YANG X D,ZHANG Q Q,WANG Y S,et al.Self-aggregated nanoparticles from methoxy poly(ethylene glycol)-modified chitosan:synthesis; characterization; aggregation and methotrexate release in vitro[J].Colloids and Surfaces B:Biointerfaces,2008,61(2):125-131.DOI:10.1016/j.colsurfb.2007.07.012.