Investigation of the Impact of Hydrolytically Cleavable Groups on the Stability of Poly(ethylene glycol) Based Hydrogels Cross-Linked via the Inverse Electron Demand Diels-Alder (iEDDA) Reaction

URN to cite this document:

urn:nbn:de:bvb:355-epub-534222 Copy

DOI to cite this document:

10.5283/epub.53422 Copy

Ziegler, Christian ; Graf, Moritz ; Nagaoka, Makoto ; Goepferich, Achim

License: Creative Commons Attribution Non-commercial No Derivatives 4.0 PDF - Published Version (1MB)

Date of publication of this fulltext: 19 Dec 2022 07:47

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This publication is part of the DEAL contract with Wiley.

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Details

Item type:	Article
Open Access Type:	DEAL (Wiley)
Journal or Publication Title:	Macromolecular Bioscience
Publisher:	Wiley
Place of Publication:	WEINHEIM
Volume:	22
Number of Issue or Book Chapter:	12
Page Range:	p. 2200226
Date:	16 September 2022
Institutions:	Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Technology (Prof. Göpferich)
Identification Number:	Value Type 10.1002/mabi.202200226 DOI
Keywords:	IN-VITRO DEGRADATION; CONTROLLED-RELEASE; PROTEIN DELIVERY; POLYVINYL-ALCOHOL) HYDROGELS; INJECTABLE HYDROGELS; PHOTOASSISTED ACCESS; SUSTAINED-RELEASE; GROWTH-FACTOR; MESH SIZE; TIME; biodegradation; hydrogel; hydrolysis; Inverse electron demand Diels-Alder reaction; leaving group
Dewey Decimal Classification:	600 Technology > 615 Pharmacy
Status:	Published
Refereed:	Yes, this version has been refereed
Created at the University of Regensburg:	Yes
Item ID:	53422

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Abstract

Eight-armed poly(ethylene glycol) (PEG) hydrogels cross-linked via inverse electron demand Diels-Alder reaction between norbornene and tetrazine groups are promising materials for long-term protein delivery. While a controlled release over 265 days is achieved for 15% w/v hydrogels in the previous study, the material shows high stability over 500 days despite having cleavable ester linkages ...

Abstract

Eight-armed poly(ethylene glycol) (PEG) hydrogels cross-linked via inverse electron demand Diels-Alder reaction between norbornene and tetrazine groups are promising materials for long-term protein delivery. While a controlled release over 265 days is achieved for 15% w/v hydrogels in the previous study, the material shows high stability over 500 days despite having cleavable ester linkages between the PEG macromonomers and their functionalities. In this study, the hydrolyzable ester linkers in the PEG-norbornene precursor structure are exchanged to reduce the degradation time. To this end, 3,6-epoxy-1,2,3,6-tetrahydrophthalimide, phenyl carbamate, carbonate ester, and phenyl carbonate ester are introduced as degradable functional groups. Oscillatory shear experiments reveal that they are not affected the in situ gelation. All hydrogel types have gel points of less than 20 s even at a low polymer concentration of 5% w/v. Hydrogels with varying polymer concentrations have similar mesh sizes, all of which fell in the range of 4-12 nm. The inclusion of phenyl carbonate ester accelerates degradation considerably, with complete dissolution of 15% w/v hydrogels after 302 days of incubation in phosphate buffer (pH 7.4). Controlled release of 150 kDa fluorescein isothiocyanate-dextran over a period of at least 150 days is achieved with 15% w/v hydrogels.

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Metadata last modified: 06 Jul 2023 12:28

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