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Fast-Forming Dissolvable Redox-Responsive Hydrogels: Exploiting the Orthogonality of Thiol–Maleimide and Thiol–Disulfide Exchange Chemistry

[Image: see text] Fast-forming yet easily dissolvable hydrogels (HGs) have potential applications in wound healing, burn incidences, and delivery of therapeutic agents. Herein, a combination of a thiol–maleimide conjugation and thiol–disulfide exchange reaction is employed to fabricate fast-forming...

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Autores principales: Altinbasak, Ismail, Kocak, Salli, Sanyal, Rana, Sanyal, Amitav
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9472223/
https://www.ncbi.nlm.nih.gov/pubmed/35696518
http://dx.doi.org/10.1021/acs.biomac.2c00209
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author Altinbasak, Ismail
Kocak, Salli
Sanyal, Rana
Sanyal, Amitav
author_facet Altinbasak, Ismail
Kocak, Salli
Sanyal, Rana
Sanyal, Amitav
author_sort Altinbasak, Ismail
collection PubMed
description [Image: see text] Fast-forming yet easily dissolvable hydrogels (HGs) have potential applications in wound healing, burn incidences, and delivery of therapeutic agents. Herein, a combination of a thiol–maleimide conjugation and thiol–disulfide exchange reaction is employed to fabricate fast-forming HGs which rapidly dissolve upon exposure to dithiothreitol (DTT), a nontoxic thiol-containing hydrophilic molecule. In particular, maleimide disulfide-terminated telechelic linear poly(ethylene glycol) (PEG) polymer and PEG-based tetrathiol macromonomers are employed as gel precursors, which upon mixing yield HGs within a minute. The selectivity of the thiol–maleimide conjugation in the presence of a disulfide linkage was established through (1)H NMR spectroscopy and Ellman’s test. Rapid degradation of HGs in the presence of thiol-containing solution was evident from the reduction in storage modulus. HGs encapsulated with fluorescent dye-labeled dextran polymers and bovine serum albumin were fabricated, and their cargo release was investigated under passive and active conditions upon exposure to DTT. One can envision that the rapid gelation and fast on-demand dissolution under relatively benign conditions would make these polymeric materials attractive for a range of biomedical applications.
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spelling pubmed-94722232022-09-15 Fast-Forming Dissolvable Redox-Responsive Hydrogels: Exploiting the Orthogonality of Thiol–Maleimide and Thiol–Disulfide Exchange Chemistry Altinbasak, Ismail Kocak, Salli Sanyal, Rana Sanyal, Amitav Biomacromolecules [Image: see text] Fast-forming yet easily dissolvable hydrogels (HGs) have potential applications in wound healing, burn incidences, and delivery of therapeutic agents. Herein, a combination of a thiol–maleimide conjugation and thiol–disulfide exchange reaction is employed to fabricate fast-forming HGs which rapidly dissolve upon exposure to dithiothreitol (DTT), a nontoxic thiol-containing hydrophilic molecule. In particular, maleimide disulfide-terminated telechelic linear poly(ethylene glycol) (PEG) polymer and PEG-based tetrathiol macromonomers are employed as gel precursors, which upon mixing yield HGs within a minute. The selectivity of the thiol–maleimide conjugation in the presence of a disulfide linkage was established through (1)H NMR spectroscopy and Ellman’s test. Rapid degradation of HGs in the presence of thiol-containing solution was evident from the reduction in storage modulus. HGs encapsulated with fluorescent dye-labeled dextran polymers and bovine serum albumin were fabricated, and their cargo release was investigated under passive and active conditions upon exposure to DTT. One can envision that the rapid gelation and fast on-demand dissolution under relatively benign conditions would make these polymeric materials attractive for a range of biomedical applications. American Chemical Society 2022-06-13 2022-09-12 /pmc/articles/PMC9472223/ /pubmed/35696518 http://dx.doi.org/10.1021/acs.biomac.2c00209 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Altinbasak, Ismail
Kocak, Salli
Sanyal, Rana
Sanyal, Amitav
Fast-Forming Dissolvable Redox-Responsive Hydrogels: Exploiting the Orthogonality of Thiol–Maleimide and Thiol–Disulfide Exchange Chemistry
title Fast-Forming Dissolvable Redox-Responsive Hydrogels: Exploiting the Orthogonality of Thiol–Maleimide and Thiol–Disulfide Exchange Chemistry
title_full Fast-Forming Dissolvable Redox-Responsive Hydrogels: Exploiting the Orthogonality of Thiol–Maleimide and Thiol–Disulfide Exchange Chemistry
title_fullStr Fast-Forming Dissolvable Redox-Responsive Hydrogels: Exploiting the Orthogonality of Thiol–Maleimide and Thiol–Disulfide Exchange Chemistry
title_full_unstemmed Fast-Forming Dissolvable Redox-Responsive Hydrogels: Exploiting the Orthogonality of Thiol–Maleimide and Thiol–Disulfide Exchange Chemistry
title_short Fast-Forming Dissolvable Redox-Responsive Hydrogels: Exploiting the Orthogonality of Thiol–Maleimide and Thiol–Disulfide Exchange Chemistry
title_sort fast-forming dissolvable redox-responsive hydrogels: exploiting the orthogonality of thiol–maleimide and thiol–disulfide exchange chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9472223/
https://www.ncbi.nlm.nih.gov/pubmed/35696518
http://dx.doi.org/10.1021/acs.biomac.2c00209
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