Study of the Degradation of Poly(ethyl glyoxylate): Biodegradation, Toxicity and Ecotoxicity Assays

Belloncle, Benjamine; Bunel, Claude; Menu-Bouaouiche, Laurence; Lesouhaitier, Olivier; Burel, Fabrice

doi:10.1007/s10924-012-0429-2

Cited by 25 publications

(29 citation statements)

References 13 publications

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“…22,28,33 As shown in Figure 1, the depolymerization products are ultimately ethanol and glyoxylic acid, a metabolic intermediate that can be processed in the liver. 36 Studies have suggested that this degradation product should exhibit low toxicity both to mammals and the environment, 37 making PEtG a promising polymer for drug delivery and other applications.…”

Section: Introductionmentioning

confidence: 99%

Poly(ethyl glyoxylate)-Poly(ethylene oxide) Nanoparticles: Stimuli-Responsive Drug Release via End-to-End Polyglyoxylate Depolymerization

2017

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The ability to disrupt polymer assemblies in response to specific stimuli provides the potential to release drugs selectively at certain sites or conditions in vivo. However, most stimuli-responsive delivery systems require many stimuli-initiated events to release drugs. "Self-immolative polymers" offer the potential to provide amplified responses to stimuli as they undergo complete end-to-end depolymerization following the cleavage of a single end-cap. Herein, linker end-caps were developed to conjugate self-immolative poly(ethyl glyoxylate) (PEtG) with poly(ethylene oxide) (PEO) to form amphiphilic block copolymers. These copolymers were self-assembled to form nanoparticles in aqueous solution. Cleavage of the linker end-caps were triggered by a thiol reducing agent, UV light, HO, and combinations of these stimuli, resulting in nanoparticle disintegration. Low stimuli concentrations were effective in rapidly disrupting the nanoparticles. Nile red, doxorubin, and curcumin were encapsulated into the nanoparticles and were selectively released upon application of the appropriate stimulus. The ability to tune the stimuli-responsiveness simply by changing the linker end-cap makes this new platform highly attractive for applications in drug delivery.

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Section: Introductionmentioning

confidence: 99%

Poly(ethyl glyoxylate)-Poly(ethylene oxide) Nanoparticles: Stimuli-Responsive Drug Release via End-to-End Polyglyoxylate Depolymerization

2017

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“…43,44 These degradation products were found to be non-toxic in a Caenorhabditis elegans (invertebrate) model. 45,46 Our group incorporated stimuli-responsive end-groups to enable triggered depolymerization of PEtG and also polymerized different glyoxylate monomers to afford a variety of triggerable polyglyoxylate homopolymers and copolymers. 40,47,48 We later showed proof of concept for the use of self-immolative PEtG and its block copolymers with poly(ethylene glycol) (PEG) in applications including drug delivery 39,40 and smart packaging sensors.…”

Section: Introductionmentioning

confidence: 99%

Controlled Polymerization of Ethyl Glyoxylate Using Alkyllithium and Alkoxide Initiators

Kenaree

Gillies

2018

Macromolecules

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The synthesis of poly(ethyl glyoxylate)s (PEtGs) by anionic polymerization was explored. PEtGs are a subclass of stimuli-responsive self-immolative polymers with promising properties for applications as coatings, sensors, and drug delivery vehicles. In this report, a new purification procedure for the preparation of highly pure ethyl glyoxylate (EtG), suitable for anionic 2 polymerization reactions, and the first successful examples of controlled polymerization of EtG are described. n-BuLi, PhLi, and t-BuLi were employed as initiators under different experimental conditions and their behavior was examined using NMR spectroscopy, size exclusion chromatography, and thermal analysis to develop an optimized procedure. As functional alkoxide initiators, propargyl alkoxide was employed in optimization studies and poly(ethylene glycol) (PEG) dialkoxide was utilized for the direct synthesis of PEtG-PEG-PEtG copolymers. The new polymerization method revealed many features of controlled polymerization reactions, yielding PEtGs with predictable molar masses and relatively low dispersity values. Supporting Information. Calculations for end-group analysis; pictures of EtG distillation setup; 1 H, 13 C{ 1 H}, and 31 P{ 1 H} NMR spectra; and SEC data for purified polymers (pdf).

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“…37 Furthermore, end-caps responsive to H 2 O 2 have been used in sensors. 31,32 Polyglyoxylates were recently reported by our group as a class of end-to-end depolymerizable polymers with attractive features such as ease of synthesis from readily available monomers, degradation to non-toxic products, 41 and the ability to undergo depolymerization in the solid state to volatile products ( Figure 1). 35 In comparison with earlier polyglyoxylates that were not responsive to stimuli, 42,43 the development of stimuli-responsive polyglyoxylates was made possible through end-capping with chloroformates.…”

Section: Introductionmentioning

confidence: 99%

End-Capping Strategies for Triggering End-to-End Depolymerization of Polyglyoxylates

2016

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Polymers that undergo end-to-end depolymerization in response to the cleavage of a stimuli-responsive end-cap are promising for diverse applications from drug delivery to responsive coatings and plastics. It is critical that the end-cap is designed to respond to an appropriate stimulus for the application. In the current work, end-caps for triggering the depolymerization of poly(ethyl glyoxylate) (PEtG) were explored. First a phenylboronate, a disulfide, and an azobenzene were utilized to impart redox-responsive properties to PEtG. Then, methoxy-substituted trityl groups were used to provide sensitivity to mild acid. A multi-responsive platform was also introduced, allowing PEtG to respond to multiple stimuli, either simultaneously or independently. Incorporation of a cross-linkable trialkene end-cap enabled the preparation of networks that could subsequently be depolymerized. Finally, high molar mass PEtG could be depolymerized by mechanical stimulation independent of the end-cap. It is anticipated that the versatility in end-capping strategies and potential depolymerization stimuli will not only expand PEtG's utility for different applications, but will also be useful for other classes of end-to-end depolymerizable polymers.

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Study of the Degradation of Poly(ethyl glyoxylate): Biodegradation, Toxicity and Ecotoxicity Assays

Cited by 25 publications

References 13 publications

Poly(ethyl glyoxylate)-Poly(ethylene oxide) Nanoparticles: Stimuli-Responsive Drug Release via End-to-End Polyglyoxylate Depolymerization

Poly(ethyl glyoxylate)-Poly(ethylene oxide) Nanoparticles: Stimuli-Responsive Drug Release via End-to-End Polyglyoxylate Depolymerization

Controlled Polymerization of Ethyl Glyoxylate Using Alkyllithium and Alkoxide Initiators

End-Capping Strategies for Triggering End-to-End Depolymerization of Polyglyoxylates

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