N-acetylcysteine side-chain functionalization of poly(globalide-co-ε-caprolactone) through thiol-ene reaction

被引:20
作者
Guindani, Camila [1 ]
Dozoretz, Pablo [1 ]
Araujo, Pedro H. H. [1 ]
Ferreira, Sandra R. S. [1 ]
de Oliveira, Debora [1 ]
机构
[1] Univ Fed Santa Catarina, Dept Chem Engn & Food Engn, EQA UFSC CP 476, BR-88040900 Florianopolis, SC, Brazil
来源
MATERIALS SCIENCE AND ENGINEERING C-MATERIALS FOR BIOLOGICAL APPLICATIONS | 2019年 / 94卷 / 477-483期
关键词
Globalide; epsilon-Caprolactone; Thiol-ene coupling; N-acetylcysteine; RING-OPENING POLYMERIZATION; ANTIOXIDANT ACTIVITY; SURFACE WETTABILITY; MOLECULAR-WEIGHT; OSTEOGENIC DIFFERENTIATION; EPSILON-CAPROLACTONE; OXIDATIVE STRESS; POLYMERS; CHEMISTRY; CELLS;
D O I
10.1016/j.msec.2018.09.060
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
N-Acetykysteine (NAC) is a drug well known for its antimucolytic action, antioxidant activity and ability to protect cells from oxidative stress. Conjugation of NAC with double bonds in the main polymer chain of poly (globalide-co-epsilon-caprolactone) (PGlCL) through thiol-ene reaction is reported. Different globalide (Gl) (an unsaturated macrolactone) to epsilon-caprolactone (CL) ratios were employed for PGICL synthesis. The polymeric materials (PGICL-NAC) were evaluated in terms of the number of functionalized double bonds, thermal properties, affinity for water and antioxidant potential. PGlCL-NAC containing more globalide repeating units presented higher degree of functionalization, due to the higher number of double bonds available to react through thiolene coupling. For high globalide contents (Gl/CL ratios above 50/50), NAC coupling in PGICL chains resulted in completely amorphous copolymers with a more hydrophilic character, which should enhance bioresorption and cell adhesion characteristics. Functionalization also gave rise to a thioether linkage, conferring to PGICL-NAC an antioxidant character, important for biomedical applications, where the material could combat cellular oxidative-stress.
引用
收藏
页码:477 / 483
页数:7
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