Study of the in vitro degradation of poly(ethyl glyoxylate)

Belloncle, Benjamine; Burel, Fabrice; Oulyadi, Hassan; Bunel, Claude

doi:10.1016/j.polymdegradstab.2008.03.004

Cited by 23 publications

(39 citation statements)

References 10 publications

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“…EtGH is known to be rapidly converted into GAH and ethanol in water. However, it has been reported that the hydrolysis of side ester groups in PEtG is rather slow at neutral pH and starts after at least 7 days of incubation in water (Belloncle et al, 2008). The hydrolysis of the side ester groups can result in free carboxylic acids which lower the pH and in turn auto-accelerate the hydrolysis of polymers via cleavages of acetal bonds.…”

Section: Discussionmentioning

confidence: 99%

“…To overcome the limitation, poly(ethyl glyoxylate) (PEtG) has been recently synthesized by anionic polymerization of ethyl glyoxylate (EtG) (Burel et al, 2003). The ultimate degradation products of PEtG, ethanol and glyoxylic acid, may justify the great potential of PEtG for pharmaceutical applications (Belloncle et al, 2008). Biodegradability and presumed biocompatibility of PEtG upon acid-catalyzed hydrolysis make PEtG as a suitable material for the development of a pH-sensitive drug delivery system.…”

Section: Introductionmentioning

confidence: 99%

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Novel pH-sensitive polyacetal-based block copolymers for controlled drug delivery

Kim

Garripelli

Jeong

et al. 2010

International Journal of Pharmaceutics

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The principal aim of this study was to synthesize and characterize pH-sensitive biodegradable triblock copolymers containing a hydrophobic polyacetal segment for controlled drug delivery. Poly(ethylene glycol)-poly(ethyl glyoxylate)-poly(ethylene glycol) (PEG-PEtG-PEG) triblock copolymers with PEG molecular weights 500 (PEtG-PEG 500 ) and 750 (PEtG-PEG 750 ) were synthesized by PEtG end-capping with methoxy PEG via a carbamate linkage. Synthesized amphiphilic PEG-PEtG-PEG was characterized by 1 H-NMR spectroscopy. Molecular weights of PEtG-PEG 500 and PEtG-PEG 750 were determined to be 2,823 and 3,387, respectively, by gel permeation chromatography. The polymers with a biodegradable polyacetal block underwent pHdependent degradation via an acid-catalyzed hydrolysis. Paclitaxel (PTX)-loaded polymeric micelles were prepared by a dialysis method and the amount of PTX incorporated into the polymeric micelle formulations was 45,000 times greater than the water solubility of PTX at room temperature. The polymeric micelles prepared from the amphiphilic PEG-PEtG-PEG triblock copolymers have released the loaded PTX in a pH-dependent manner. The novel PEtG-based amphiphilic block copolymers can find applications for targeted and controlled drug delivery to the acidic environments found in tumors and intracellular compartments.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Novel pH-sensitive polyacetal-based block copolymers for controlled drug delivery

Kim

Garripelli

Jeong

et al. 2010

International Journal of Pharmaceutics

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“…23 Glyoxylate monomers such as ethyl glyoxylate (EtG) are commercially available or can be prepared from readily available starting materials such as maleic or fumaric acid. 23 In addition, they ultimately degrade to glyoxylic acid, [35][36][37] a metabolite found in some mammalian biochemical pathways 38 and an intermediate in the glyoxylate cycle, an anaerobic variant of the tricarboxylic acid cycle that occurs in plants, bacteria, protists, and fungi. 37 Here we explore in detail the degradation of endcapped self-immolative poly(ethyl glyoxylate) (PEtG).…”

Section: Introductionmentioning

confidence: 99%

“…23 In addition, they ultimately degrade to glyoxylic acid, [35][36][37] a metabolite found in some mammalian biochemical pathways 38 and an intermediate in the glyoxylate cycle, an anaerobic variant of the tricarboxylic acid cycle that occurs in plants, bacteria, protists, and fungi. 37 Here we explore in detail the degradation of endcapped self-immolative poly(ethyl glyoxylate) (PEtG). In particular, the solid-state degradation of PEtG demonstrates several important novel and unusual aspects of the end-to-end depolymerization and also reveals that upon end-cap cleavage, PEtG undergoes depolymerization under ambient conditions to afford volatile products.…”

Section: Introductionmentioning

confidence: 99%

Photocontrolled Degradation of Stimuli-Responsive Poly(ethyl glyoxylate): Differentiating Features and Traceless Ambient Depolymerization

et al. 2016

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The depolymerization of coatings prepared from a 6-nitroveratryl carbonate end-capped poly(ethyl glyoxylate) (PEtG) self-immolative polymer was studied. This polymer undergoes end-to-end depolymerization following cleavage of the end-cap by UV light. Several important fundamental differences between this class of polymers and conventional degradable polymers were revealed. For example, polymer backbone cleavage and depolymerization exhibited different dependencies on pH, emphasizing the decoupling of these processes. Probing of the coating erosion mechanism illustrated an interesting combination of features from surface erosion and bulk degradation mechanisms that arise from the end-to-end depolymerization mechanism and further differentiate these polymers from convention degradable polymers. It was also demonstrated that unlike backbone cleavage, PEtG depolymerization did not exhibit a dependence on water, and that PEtG could depolymerize back to the volatile monomer ethyl glyoxylate at ambient temperature and pressure. This unusual feature was utilized to perform facile polymer reprogramming/recycling via an irradiation-trapping-repolymerization sequence as well as polymer patterning by a simple irradiation-evaporation sequence.

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“…We recently reported polyglyoxylates as a class of polyacetal‐based SIPs . They can be prepared from commercial monomers including ethyl glyoxylate and degrade to environmentally benign products such as glyoxylic acid and ethanol . Unlike other SIPs, polyglyoxylates can also degrade to volatile products (e.g., ethyl glyoxylate), so they undergo rapid depolymerization in the solid state .…”

Section: Introductionmentioning

confidence: 99%

Depolymerization of Trityl End‐Capped Poly(Ethyl Glyoxylate): Potential Applications in Smart Packaging

Fan

Salazar

Gillies

2018

Macromol. Rapid Commun.

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The temperature-dependent depolymerization of self-immolative poly(ethyl glyoxylate) (PEtG) capped with triphenylmethyl (trityl) groups is studied and its potential application for smart packaging is explored. PEtGs with four different trityl end-caps are prepared and found to undergo depolymerization to volatile products from the solid state at different rates depending on temperature and the electron-donating substituents on the trityl aromatic rings. Through the incorporation of hydrophobic dyes including Nile red and IR-780, the depolymerization is visualized as a color change of the dye as it changes from a dispersed to aggregated state. The ability of this platform to provide information on thermal history through an easily readable signal makes it promising in smart packaging applications for sensitive products such a food and other cargo that is susceptible to degradation.

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Study of the in vitro degradation of poly(ethyl glyoxylate)

Cited by 23 publications

References 10 publications

Novel pH-sensitive polyacetal-based block copolymers for controlled drug delivery

Novel pH-sensitive polyacetal-based block copolymers for controlled drug delivery

Photocontrolled Degradation of Stimuli-Responsive Poly(ethyl glyoxylate): Differentiating Features and Traceless Ambient Depolymerization

Depolymerization of Trityl End‐Capped Poly(Ethyl Glyoxylate): Potential Applications in Smart Packaging

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