Chemical functionalization of hyaluronic acid for drug delivery applications

被引:138
作者
Vasi, Ana-Maria [1 ]
Popa, Marcel Ionel [1 ]
Butnaru, Maria [2 ]
Dodi, Gianina [1 ,3 ]
Verestiuc, Liliana [2 ]
机构
[1] Gheorghe Asachi Tech Univ Iasi, Fac Chem Engn & Environm Protect, Iasi 700050, Romania
[2] Grigore T Popa Univ Med Pharm, Fac Med Bioengn, Iasi 700454, Romania
[3] SCIENT Res Ctr Instrumental Anal SC, CROMATEC PLUS, Bucharest 060114, Romania
来源
MATERIALS SCIENCE & ENGINEERING C-MATERIALS FOR BIOLOGICAL APPLICATIONS | 2014年 / 38卷
关键词
Functionalized hyaluronic acid; Ring opening mechanism; Gels; Acrylic acid; Pilocarpine; SUSTAINED-RELEASE FORMULATION; MOLECULAR-WEIGHT; DEGRADATION; MECHANISM; HYDROGELS; SYSTEM; DILUTE;
D O I
10.1016/j.msec.2014.01.052
中图分类号
TB3 [工程材料学]; R318.08 [生物材料学];
学科分类号
0805 ; 080501 ; 080502 ;
摘要
Functionalized hyaluronic acid (HA) derivatives were obtained by ring opening mechanism of maleic anhydride (MA). FTIR and H-1 NMR spectroscopy were used to confirm the chemical linkage of MA on the hyaluronic acid chains. Thermal analysis (TG-DTG and DSC) and GPC data for the new products revealed the formation of new functional groups, without significant changes in molecular weight and thermal stability. New gels based on hyaluronic acid modified derivatives were obtained by acrylic acid copolymerization in the presence of a redox initiation system. The resulted circular and interconnected pores of the gels were visualized by SEM. The release profiles of an ophthalmic model drug, pilocarpine from tested gels were studied in simulated media. Evaluation of the cytotoxicity and cell proliferation properties indicates the potential of the new systems to be used in contact with biological media in drug delivery applications. (C) 2014 Elsevier B.V. All rights reserved.
引用
收藏
页码:177 / 185
页数:9
相关论文
共 43 条
[1]   Characterization of enzymatically digested hyaluronic acid using NMR, Raman, IR, and UV-Vis spectroscopies [J].
Alkrad, JA ;
Mrestani, Y ;
Stroehl, D ;
Wartewig, S ;
Neubert, R .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2003, 31 (03) :545-550
[2]  
BALAZS EA, 1993, J RHEUMATOL, V20, P3
[3]  
BALAZS EA, 1983, HEALON SODIUM HYALUR
[4]   Stability evaluation of n-alkyl hyaluronic acid derivates by DSC and TG measurement [J].
Benesová, K ;
Pekar, M ;
Lapcík, L ;
Kucerík, J .
JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY, 2006, 83 (02) :341-348
[5]   New associative systems based on alkylated hyaluronic acid.: Synthesis and aqueous solution properties [J].
Creuzet, C ;
Kadi, S ;
Rinaudo, M ;
Auzléy-Velty, R .
POLYMER, 2006, 47 (08) :2706-2713
[6]   Preparation and structural characterisation of novel and versatile amphiphilic octenyl succinic anhydride-modified hyaluronic acid derivatives [J].
Eenschooten, Corinne ;
Guillaumie, Fanny ;
Kontogeorgis, Georgios M. ;
Stenby, Erling H. ;
Schwach-Abdellaoui, Khadija .
CARBOHYDRATE POLYMERS, 2010, 79 (03) :597-605
[7]  
EENSCHOOTEN SC, 2007, Patent No. 20070987701
[8]   Liposomal diclofenac eye drop formulations targeting the retina: Formulation stability improvement using surface modification of liposomes [J].
Fujisawa, Takuya ;
Miyai, Hiroko ;
Hironaka, Kohei ;
Tsukamoto, Toshimasa ;
Tahara, Kohei ;
Tozuka, Yuichi ;
Ito, Masaki ;
Takeuchi, Hirofumi .
INTERNATIONAL JOURNAL OF PHARMACEUTICS, 2012, 436 (1-2) :564-567
[9]   Potential mechanism of action of intra-articular hyaluronan therapy in osteoarthritis: Are the effects molecular weight dependent? [J].
Ghosh, P ;
Guidolin, D .
SEMINARS IN ARTHRITIS AND RHEUMATISM, 2002, 32 (01) :10-37
[10]   The magic glue hyaluronan and its eraser hyaluronidase: A biological overview [J].
Girish, K. S. ;
Kemparaju, K. .
LIFE SCIENCES, 2007, 80 (21) :1921-1943