Polyme phân hủy sinh học từ Xylitol

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Polyme phân hủy sinh học từ Xylitol COMMUNICATIONDOI: 10.1002/adma.200702377Biodegradable Xylitol-Based Polymers**By Joost P. Bruggeman, Christopher J. Bettinger, Christiaan L.E. Nijst, Daniel S. Kohane,and Robert Langer* Synthetic biodegradable polymers have made a consider- photocrosslinkable hydrogel. Polycondensation of xylitol withable impact in various fields of biomedical engineering, such as the water-insoluble sebacic acid monomer produced tough,drug delivery and tissue engineering. The design of synthetic biodegradable elastomers with tunable mechanical andbiodegradable polymers for bioengineering purposes is degradation properties. These xylitol-based polymers exhib-challenging because of the application-specific constraints on ited excellent in vitro and in vivo biocompatibility compared tothe physical properties, including mechanical compliance and the well-characterized poly(L-lactic-co-glycolic acid) (PLGA),degradation rates, and the need for biocompatibility and low and are promising biomaterials.cytotoxicity.[1] The monomer selection frequently limits the Sebacic acid (a metabolite in the oxidation of fatty acids)range of required material properties. Our goal was to design a and citric acid (a metabolite in the Krebs cycle) were chosen as the reacting monomers for their proven biocompatibility;[2,3]class of synthetic biopolymers based on a monomer thatpossesses a wide range of properties that are biologically they are also FDA-approved compounds. Polycondensation ofrelevant. This monomer ideally should be: (1) multifunctional xylitol with sebacic acid produced water-insoluble waxyto allow the formation of randomly crosslinked networks prepolymers (termed PXS prepolymers). PXS prepolymersand a wide range of crosslinking densities; (2) nontoxic; with a monomer ratio of xylitol: sebacic acid of 1:1 and 1:2 were(3) endogenous to the human metabolic system; (4) FDA synthesized and had a weight-average molecular weight (Mw) of 2443 g/mol (Mn ¼ 1268 g/mol, polydispersity index (PDI)approved; and (5) preferably inexpensive. We chose xylitol as 1.9) and 6202 g/mol (Mn ¼ 2255 g/mol, PDI 2.7), respectively.it meets these criteria. We hypothesized that biodegradablepolyesters could be obtained through copolymerization The PXS prepolymers were melted into the desired form andreactions with polycarboxylic acids; the hydration of such cured by polycondensation (120 8C, 40 m Torr for 4 days, 1 Torr ¼ 133.3 Pa) to yield low-modulus (PXS 1:1) andbiodegradable polymers could be controlled by tuning thedifferent compositions and stoichiometry of the reacting high-modulus (PXS 1:2) elastomers. PXS prepolymers aremonomer. Here, we describe xylitol-based polymers that soluble in ethanol, dimethyl sulfoxide, tetrahydrofuran andrealize this design. Polycondensation of xylitol with water- acetone, which allows processing into more complex geome-soluble citric acid yielded biodegradable, water-soluble tries. Polycondensation of xylitol with citric acid resulted in apolymers. Acrylation of this polymer resulted in an elastomeric water-soluble prepolymer (designated PXC prepolymer), of which the Mw was 298 066 g/mol and the Mn was 22 305 g/mol (PDI 13.4), compared to linear poly(ethylene glycol) (PEG) standards. To crosslink the water-soluble PXC prepolymer in [*] Prof. R. Langer, Dr. J. P. Bruggeman, C. L. E. Nijst Department of Chemical Engineering an aqueous environment, we functionalized the hydroxyl Massachusetts Institute of Technology groups of PXC with vinyl groups (designated PXCma) using Cambridge, MA 02139 (USA) methacrylic anhydride, as previously de ...