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Tweaking the acid-sensitivity of transiently thermoresponsive Polyacrylamides with cyclic acetal repeating units

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Abstract

Merging the characteristics of thermoresponsive and stimuli-degradable polymers yields so-called transiently thermoresponsive polymers, which can find application for the design of injectable gels, nanoparticles, etc. within a biomedical context. Among these polymers, only a limited number is reported which shows selective degradation under mild acidic conditions. However, extension of the library of transiently thermoresponsive polymers is desired to broadening the biomaterials toolbox to suit specific needs. Three monomers were developed by modification of 2-hydroxyethylacrylamide (HEAm) via tetrahydropyranylation or -furanylation with 3,4-dihydro-2H-pyran (DHP), 2,3-dihydrofuran (DHF) or 2,3-dihydro-5-methylfuran (MeDHF). The presence of an acetal or ketal bond provided the monomers a pH-dependent hydrolysis behavior ranging from minutes to days. RAFT polymerisation allowed for the construction of homopolymers with temperature responsive behavior and pH-dependent hydrolysis which was strongly influenced by nature of the monomeric repeating units.

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Acknowledgements

This work was supported by Ghent University through the BOF-GOA grant scheme.

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Authors and Affiliations

  1. Department of Pharmaceutics, Ghent University, Ghent, Belgium

    Simon Van Herck & Bruno G. De Geest

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  1. Simon Van Herck
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  2. Bruno G. De Geest
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Correspondence to Bruno G. De Geest.

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Conflict of interest The authors declare that they have no conflict of interest.

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Van Herck, S., De Geest, B.G. Tweaking the acid-sensitivity of transiently thermoresponsive Polyacrylamides with cyclic acetal repeating units. Sci. China Chem. 63, 504–512 (2020). https://doi.org/10.1007/s11426-019-9705-4

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  • DOI: https://doi.org/10.1007/s11426-019-9705-4

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