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The Synthesis and Biodegradability of Poly(lactide-random-depsipeptide)-PEGPoly(lactide-random-depsipeptide) ABA-type Triblock Copolymers

Department of Applied Chemistry, Faculty of Engineering, and High Technology Research Center, Kansai University, 3-3-35 Yamate-cho, Suita, Osaka 564-8680, Japanyohya{at}ipcku.kansai-u.ac.jp

Takao Nakai

Koji Nagahama

Department of Applied Chemistry, Faculty of Engineering, and High Technology Research Center, Kansai University, 3-3-35 Yamate-cho, Suita, Osaka 564-8680, Japan

Tatsuro Ouchi

Department of Applied Chemistry, Faculty of Engineering, and High Technology Research Center, Kansai University, 3-3-35 Yamate-cho, Suita, Osaka 564-8680, Japantouchi{at}ipcku.kansai-u.ac.jp

Shinji Tanaka

Kenji Kato

NOF Corporation Tsukuba Research Laboratory, 5-10, Tokodai, Tsukuba, Ibaragi 300-2635, Japan

Amphiphilic ABA-type triblock copolymers were synthesized to develop a biodegradable anti-adhesive membrane. In this particular synthesis, poly[L-lactide(LA)-co-depsipeptide] (poly[LA-co-(Glc-Leu)]: PLGL) was used as the A segment, and the poly(ethylene glycol)s (PEG)s, Mn 10,000 and Mn 20,500 were used as the B segment. The synthesis of the triblock copolymer (PLGL-PEG-PLGL) was carried out via a ring-opening copolymerization of L-lactide and cyclo(Glc-Leu) in the presence of hydroxytelechelic poly(ethylene glycol) using tin 2-ethylhexanoate as a catalyst. To evaluate the copolymer films as candidates for biodegradable anti-adhesive membranes, physicochemical properties such as degradation on behavior under physiological conditions and water absorption were investigated. The degradation rate of the PLGLPEG-PLGL films varied with changes in the molecular architecture; specifically, the molecular weight of the hydrophilic B segment and the depsipeptide unit content in the A segment were more prominent. The biocompatibility and resorption of the PLGL-PEG-PLGL films were also evaluated. The PLGLPEG-PLGL films were degraded and depleted gradually in vivo without inflammation.

Key Words: polydepsipeptide • polylactide • PEG • biodegradable polymer

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