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Acid-labile thermoresponsive copolymers that combine fast pH-triggered hydrolysis and high stability under neutral conditions

Qilu Zhang (UGent) , Zhanyao Hou (UGent) , Benoit Louage (UGent) , Dingying Zhou (UGent) , Nane Vanparijs (UGent) , Bruno De Geest (UGent) and Richard Hoogenboom (UGent)
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Abstract
Biodegradable polymeric materials are intensively used in biomedical applications. Of particular interest for drug-delivery applications are polymers that are stable at pH7.4, that is, in the blood stream, but rapidly hydrolyze under acidic conditions, such as those encountered in the endo/lysosome or the tumor microenvironment. However, an increase in the acidic-degradation rate of acid-labile groups goes hand in hand with higher instability of the polymer at pH7.4 or during storage, thus posing an intrinsic limitation on fast degradation under acidic conditions. Herein, we report that a combination of acid-labile dimethyldioxolane side chains and hydroxyethyl side chains leads to acid-degradable thermoresponsive polymers that are quickly hydrolyzed under slightly acidic conditions but stable at pH7.4 or during storage. We ascribe these properties to high hydration of the hydroxy-containing collapsed polymer globules in conjunction with autocatalytic acceleration of the hydrolysis reactions by the hydroxy groups.
Keywords
RESPONSIVE POLYMERS, GENE DELIVERY, CONTROLLED-RELEASE, RADICAL POLYMERIZATION, 2-HYDROXYETHYL ACRYLATE, 2-METHOXYETHYL ACRYLATE, DRUG-DELIVERY, BIODEGRADABLE POLYMERS, thermoresponsive polymers, pH-responsive polymers, biodegradable polymers, drug delivery, biomaterials, RAFT PROCESS, DEXTRAN

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MLA
Zhang, Qilu, et al. “Acid-Labile Thermoresponsive Copolymers That Combine Fast PH-Triggered Hydrolysis and High Stability under Neutral Conditions.” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol. 54, no. 37, 2015, pp. 10879–83, doi:10.1002/anie.201505145.
APA
Zhang, Q., Hou, Z., Louage, B., Zhou, D., Vanparijs, N., De Geest, B., & Hoogenboom, R. (2015). Acid-labile thermoresponsive copolymers that combine fast pH-triggered hydrolysis and high stability under neutral conditions. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 54(37), 10879–10883. https://doi.org/10.1002/anie.201505145
Chicago author-date
Zhang, Qilu, Zhanyao Hou, Benoit Louage, Dingying Zhou, Nane Vanparijs, Bruno De Geest, and Richard Hoogenboom. 2015. “Acid-Labile Thermoresponsive Copolymers That Combine Fast PH-Triggered Hydrolysis and High Stability under Neutral Conditions.” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 54 (37): 10879–83. https://doi.org/10.1002/anie.201505145.
Chicago author-date (all authors)
Zhang, Qilu, Zhanyao Hou, Benoit Louage, Dingying Zhou, Nane Vanparijs, Bruno De Geest, and Richard Hoogenboom. 2015. “Acid-Labile Thermoresponsive Copolymers That Combine Fast PH-Triggered Hydrolysis and High Stability under Neutral Conditions.” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 54 (37): 10879–10883. doi:10.1002/anie.201505145.
Vancouver
1.
Zhang Q, Hou Z, Louage B, Zhou D, Vanparijs N, De Geest B, et al. Acid-labile thermoresponsive copolymers that combine fast pH-triggered hydrolysis and high stability under neutral conditions. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. 2015;54(37):10879–83.
IEEE
[1]
Q. Zhang et al., “Acid-labile thermoresponsive copolymers that combine fast pH-triggered hydrolysis and high stability under neutral conditions,” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol. 54, no. 37, pp. 10879–10883, 2015.
@article{7140228,
  abstract     = {{Biodegradable polymeric materials are intensively used in biomedical applications. Of particular interest for drug-delivery applications are polymers that are stable at pH7.4, that is, in the blood stream, but rapidly hydrolyze under acidic conditions, such as those encountered in the endo/lysosome or the tumor microenvironment. However, an increase in the acidic-degradation rate of acid-labile groups goes hand in hand with higher instability of the polymer at pH7.4 or during storage, thus posing an intrinsic limitation on fast degradation under acidic conditions. Herein, we report that a combination of acid-labile dimethyldioxolane side chains and hydroxyethyl side chains leads to acid-degradable thermoresponsive polymers that are quickly hydrolyzed under slightly acidic conditions but stable at pH7.4 or during storage. We ascribe these properties to high hydration of the hydroxy-containing collapsed polymer globules in conjunction with autocatalytic acceleration of the hydrolysis reactions by the hydroxy groups.}},
  author       = {{Zhang, Qilu and Hou, Zhanyao and Louage, Benoit and Zhou, Dingying and Vanparijs, Nane and De Geest, Bruno and Hoogenboom, Richard}},
  issn         = {{1433-7851}},
  journal      = {{ANGEWANDTE CHEMIE-INTERNATIONAL EDITION}},
  keywords     = {{RESPONSIVE POLYMERS,GENE DELIVERY,CONTROLLED-RELEASE,RADICAL POLYMERIZATION,2-HYDROXYETHYL ACRYLATE,2-METHOXYETHYL ACRYLATE,DRUG-DELIVERY,BIODEGRADABLE POLYMERS,thermoresponsive polymers,pH-responsive polymers,biodegradable polymers,drug delivery,biomaterials,RAFT PROCESS,DEXTRAN}},
  language     = {{eng}},
  number       = {{37}},
  pages        = {{10879--10883}},
  title        = {{Acid-labile thermoresponsive copolymers that combine fast pH-triggered hydrolysis and high stability under neutral conditions}},
  url          = {{http://doi.org/10.1002/anie.201505145}},
  volume       = {{54}},
  year         = {{2015}},
}

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