Acid‐Cleavable Poly(ethylene glycol) Hydrogels Displaying Protein Release at pH 5

Johannes, Ewald; Blankenburg, Jan; Worm, Matthias; Besch, Laura; Unger, Ronald E.; Tremel, Wolfgang; Frey, Holger; Pohlit, Hannah

doi:10.1002/chem.201905310

Cited by 5 publications

(3 citation statements)

References 55 publications

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“…Previously reported strategies of synthesizing degradable polyethers involve the incorporation of heterofunctionality into the polyether backbone through copolymerization of epoxides with lactones or anhydrides, − the incorporation of acetal linkages through end-group modification followed by intermolecular condensation, , or vinyl ethers derived from copolymerization followed by postpolymerization modification. − In all of these applications, either careful selection of catalytic method for balanced comonomer reactivity or postpolymerization modification is required.…”

Section: Introductionmentioning

confidence: 99%

Concurrent Ring-Opening/Ring-Closing Polymerization of Glycidyl Acetate to Acid-Degradable Poly(ether-co-orthoester) Materials Using a Mono(μ-alkoxo)bis(alkylaluminum) Initiator

et al. 2022

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Orthoester-containing copolymers are degradable under mild acidic conditions, making them attractive candidates for applications in drug delivery, photolithography, or disposable plastics with a built-in mechanism for environmental remediation. Orthoester linkages may be incorporated into polyether backbones by a chain-growth ring-opening and subsequent ring-closing polymerization of glycidyl acetate (GA) and methyl glycidyl acetate (MGA) monomers, where both epoxy and carbonyl groups participate in orthoester formation using a mono(μ-alkoxo)bis(alkylaluminum) (MOB) initiator. MGA exists as a mixture of (S,S)/(R,R)- and (S,R)/(R,S)-diastereomers, and MOB-initiated polymerization exhibited a strong preference for the (S,R)/(R,S)-diastereomer. Copolymerization between GA and a conventional epoxide monomer resulted in materials combining the facile degradation of polyorthoesters with the structural diversity of polyethers. We demonstrated the synthesis of degradable linear chains with methyl, allyl ether, propenyl ether, and methylene chloride pendant groups with weight average molecular weights ranging from 6.1 to 18.4 kg/mol. Additionally, we demonstrated the synthesis of degradable, polarity-switching cross-linked networks with acid-cleavable orthoester linkages and propenyl ether pendant groups that slowly degrade under mild acidic conditions without swelling.

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Section: Introductionmentioning

confidence: 99%

Concurrent Ring-Opening/Ring-Closing Polymerization of Glycidyl Acetate to Acid-Degradable Poly(ether-co-orthoester) Materials Using a Mono(μ-alkoxo)bis(alkylaluminum) Initiator

et al. 2022

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“…Modified difunctional water-soluble PEG dimethacrylate (PEG-acetal-DMA) macromonomers have cleavable acetal units ( 49 ), and when those were filled with allergen (OVA, grass pollen allergen, HDM allergen) and encapsulated into liposomes, they could avoid IgE-dependent activation of basophils in vitro , but were taken up by dendritic cells ( 50 ).…”

Section: Allergens Administered With Novel Adjuvantsmentioning

confidence: 99%

Formulations for Allergen Immunotherapy in Human and Veterinary Patients: New Candidates on the Horizon

Pali‐Schöll

DeBoer

Alessandri³

et al. 2020

Front. Immunol.

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Allergen immunotherapy is currently the only causal treatment for allergic diseases in human beings and animals. It aims to redirect the immune system into a tolerogenic or desensitized state. Requirements include clinical efficacy, safety, and schedules optimizing patient or owner compliance. To achieve these goals, specific allergens can be formulated with adjuvants that prolong tissue deposition and support uptake by antigen presenting cells, and/or provide a beneficial immunomodulatory action. Here, we depict adjuvant formulations being investigated for human and veterinary allergen immunotherapy.

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“…1,22,24,26 Additional environmental conditions, including pH and temperature, also influence degradation and should be considered both in terms of in vivo performance and influence on in vitro testing results. [25][26][27] All these factors collectively determine the rate at which the hydrogel breaks down and are important considerations in hydrogel design for target applications.…”

Section: Introductionmentioning

confidence: 99%

A user's guide to degradation testing of polyethylene glycol‐based hydrogels: From in vitro to in vivo studies

Rodriguez‐Rivera,

Green,

Shah

et al. 2023

J Biomedical Materials Res

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Poly(ethylene glycol) (PEG)‐based hydrogels have gained significant attention in the field of biomedical applications due to their versatility and antifouling properties. Acrylate‐derivatized PEG hydrogels (PEGDA) are some of the most widely studied hydrogels; however, there has been debate around the degradation mechanism and predicting resorption rates. Several factors influence the degradation rate of PEG hydrogels, including backbone and endgroup chemistry, macromer molecular weight, and polymer concentration. In addition to hydrogel parameters, it is necessary to understand the influence of biological and environmental conditions (e.g., pH and temperature) on hydrogel degradation. Rigorous methods for monitoring degradation in both in vitro and in vivo settings are also critical to hydrogel design and development. Herein, we provide guidance on tailoring PEG hydrogel chemistry to achieve target hydrolytic degradation kinetics for both resorbable and biostable applications. A detailed overview of accelerated testing methods and hydrogel degradation characterization is provided to aid researchers in experimental design and interpreting in vitro–in vivo correlations necessary for predicting hydrogel device performance.

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Acid‐Cleavable Poly(ethylene glycol) Hydrogels Displaying Protein Release at pH 5

Cited by 5 publications

References 55 publications

Concurrent Ring-Opening/Ring-Closing Polymerization of Glycidyl Acetate to Acid-Degradable Poly(ether-co-orthoester) Materials Using a Mono(μ-alkoxo)bis(alkylaluminum) Initiator

Concurrent Ring-Opening/Ring-Closing Polymerization of Glycidyl Acetate to Acid-Degradable Poly(ether-co-orthoester) Materials Using a Mono(μ-alkoxo)bis(alkylaluminum) Initiator

Formulations for Allergen Immunotherapy in Human and Veterinary Patients: New Candidates on the Horizon

A user's guide to degradation testing of polyethylene glycol‐based hydrogels: From in vitro to in vivo studies

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