Enzymatic synthesis and characterization of novel biodegradable copolymers of 5-benzyloxy-trimethylene carbonate with 1,4-dioxan-2-one.
Enzymatic ring-opening copolymerization of 5-benzyloxy-trimethylene carbonate (BTMC) and 1,4-dioxan-2-one (DON) was investigated for the first time. Immobilized porcine pancreas lipase (IPPL) on silica particles was selected to perform the copolymerization. A series of novel biodegradable copolymers with different compositions were characterized by (1)H NMR, (13)C NMR, and GPC. The influences of reaction conditions such as polymerization time and catalyst concentration on the yield and molecular weight of the copolymers were also studied. The copolymerizations of different monomer feed ratios were carried out in bulk at 150 degrees C with 4.5 wt per thousand IPPL as a catalyst for 24 h. With the increase of the BTMC molar feed ratio from 20% to 79%, the M(n) of the resulting copolymers increased from 5600 to 63400. Water uptake and static contact angle experiments showed that the hydrophilicity of copolymers could be improved with increasing DON content in the copolymers. Moreover, the in vitro drug release rate (ibuprofen as the model drug) of the resulting copolymers also increased along with the DON content in the copolymers.
He
Feng
F
Key Laboratory of Biomedical Polymers of the Ministry of Education, Department of Chemistry, Wuhan University, Wuhan 430072, China. fenghe2002@hotmail.com
Jia
Hua-Li
HL
Liu
Gang
G
Wang
Yan-Ping
YP
Feng
Jun
J
Zhuo
Ren-Xi
RX
D018712:Analgesics, Non-Narcotic / Q000737:chemistry*; D000818:Animals; D001672:Biocompatible Materials; D001673:Biodegradation, Environmental; D003692:Delayed-Action Preparations / Q000138:chemical synthesis / Q000737:chemistry; D004146:Dioxanes / Q000737:chemistry*; D007052:Ibuprofen / Q000737:chemistry*; D008049:Lipase / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D013552:Swine
D018712:Analgesics, Non-Narcotic; D001672:Biocompatible Materials; D003692:Delayed-Action Preparations; D004146:Dioxanes; D011108:Polymers; C443643:trimethylene carbonate; D008049:Lipase; C025223:1,4-dioxane; D007052:Ibuprofen