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Poly[(ethylene oxide)-co-(methylene ethylene oxide)]: A hydrolytically-degradable poly(ethylene oxide) platform.

ABSTRACT: A facile method for imparting hydrolytic degradability to poly(ethylene oxide) (PEO), compatible with current PEGylation strategies, is presented. By incorporating methylene ethylene oxide (MEO) units into the parent PEO backbone, complete degradation was defined by the molar incorporation of MEO, and the structure of the degradation byproducts was consistent with an acid-catalyzed vinyl-ether hydrolysis mechanism. The hydrolytic degradation of poly[(ethylene oxide)-co-(methylene ethylene oxide)] was pH-sensitive, with degradation at pH 5 being significantly faster than at pH 7.4 at 37 °C in PBS buffer while long-term stability could be obtained in either the solid-state or at pH 7.4 at 6 °C.

SUBMITTER: Lundberg P

PROVIDER: S-EPMC3509790 | biostudies-literature | 2012 Nov

REPOSITORIES: biostudies-literature

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Poly[(ethylene oxide)-co-(methylene ethylene oxide)]: A hydrolytically-degradable poly(ethylene oxide) platform.

Lundberg Pontus P Lee Bongjae F BF van den Berg Sebastiaan A SA Pressly Eric D ED Lee Annabelle A Hawker Craig J CJ Lynd Nathaniel A NA

ACS macro letters 20121010 11

A facile method for imparting hydrolytic degradability to poly(ethylene oxide) (PEO), compatible with current PEGylation strategies, is presented. By incorporating methylene ethylene oxide (MEO) units into the parent PEO backbone, complete degradation was defined by the molar incorporation of MEO, and the structure of the degradation byproducts was consistent with an acid-catalyzed vinyl-ether hydrolysis mechanism. The hydrolytic degradation of poly[(ethylene oxide)-co-(methylene ethylene oxide) ...[more]

PMID: 23205320

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Project description:Poly(lactic acid) choline iodide ester methacrylate, poly(PLA4ChMA), is a cationic degradable polymer that can flocculate particles and dewater oil sands from tailings ponds. This novel material has yet to be characterized in terms of environmental and human health. If ingested, this substance may become bioaccessible. The bioaccessibility (bioaccessible fraction) of an ingested contaminant is a measure of the portion of an ingested dose that solubilizes and may be available for systemic absorption. In the present study, the partially degraded flocculant and its degradation products, modelled using lactic acid and choline chloride, were subjected to a modified physiologically based extraction test (PBET). Bioaccessible fractions were estimated by proton nuclear magnetic resonance (1H-NMR) spectroscopy and by high-performance liquid chromatography (HPLC). The measured bioaccessibility of lactic acid in gastric solution containing choline chloride is ∼100% but slightly dropped to 94% in intestinal solution at a solid-to-liquid ratio of 1:200. The partially degraded poly(PLA4ChMA) did not degrade further during the PBET and is not solubilized (i.e., 0% bioaccessibility) in the gastric phase but is fully solubilized (i.e., 100% bioaccessibility) in the intestinal phase. At the end of PBET intestinal digestion, the molar ratio of lactic acid to choline chloride in the presence of degraded poly(PLA4ChMA) was 2, approximately the same as in the initial solution. Thus, lactic acid and choline chloride are solubilized to the same extents in both gastric and intestinal solutions. Results suggest that HPLC can be used to directly estimate the bioaccessibility of lactic acid, whereas 1H - NMR may be used to indirectly quantify the bioaccessibility of both lactic acid and choline chloride by determining their molar ratio in PBET extracts. In future works, these findings may be applied to the estimation of risks from exposure to poly(PLA4ChMA) as well as to the remediation of contaminants flocculated by poly(PLA4ChMA) in tailings ponds and in other wastewaters.

Dataset Information

Poly[(ethylene oxide)-co-(methylene ethylene oxide)]: A hydrolytically-degradable poly(ethylene oxide) platform.

Publications

Poly[(ethylene oxide)-co-(methylene ethylene oxide)]: A hydrolytically-degradable poly(ethylene oxide) platform.

Similar Datasets

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