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Interfacially Hydrazone Cross-linked Thermosensitive Polymeric Micelles for Acid-Triggered Release of Paclitaxel

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    Interfacially Hydrazone Cross-linked Thermosensitive Polymeric Micelles for Acid-Triggered Release of Paclitaxel
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    Department of Pharmaceutics, Utrecht Institute for Pharmaceutical Sciences (UIPS), Utrecht University, Universiteitsweg 99, 3508 TB Utrecht, The Netherlands
    *E-mail: [email protected]. Tel.: + 31 30 253 6964. Fax: + 31 30 251 7839.
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    ACS Biomaterials Science & Engineering

    Cite this: ACS Biomater. Sci. Eng. 2015, 1, 6, 393–404
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    https://doi.org/10.1021/acsbiomaterials.5b00006
    Published April 29, 2015
    Copyright © 2015 American Chemical Society
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    Abstract

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    Polymeric micelles are widely studied as drug carriers, but their poor in vivo stability and, as a consequence, premature drug release hampers their use for targeted drug delivery. Reversible cross-linking of polymeric micelles to achieve stability in the circulation and triggered de-cross-linking/drug release at their site of action is a highly attractive approach to design effective targeted nanomedicines. In this study, the synthesis and RAFT polymerization of a reactive ketone-containing methacrylamide monomer, 1-(acetonylamino)-2-methyl-2-propen-1-one (AMPO), was investigated. A triblock thermosensitive polymer p(HPMAm)-b-p(AMPO)-b-p(HPMAm-Bz-co-HPMAm-Lac) was synthesized by sequential RAFT polymerization of HPMAm for the permanently hydrophilic block, AMPO for the cross-linkable middle block, and HPMAm-Bz with HPMAm-Lac for the thermosensitive block. The triblock copolymer self-assembled into polymeric micelles with size of 52 nm (PDI of 0.03) by increasing the temperature of an aqueous polymer solution above its critical micelle temperature (3 °C). The micelles were subsequently cross-linked after addition of adipic acid dihydrazide, which reacts with the ketone groups of p(AMPO) located at the interfacial region of the micelles. The cross-linked micelles displayed substantially increased thermal and hydrolytic stability as compared to non-cross-linked micelles. The hydrazone bonds in the cross-links were, however, prone to hydrolysis at mild acidic condition (pH 5.0). A chemotherapeutic drug, paclitaxel, was encapsulated in the polymeric micelles with a high loading capacity (29 wt %). The retention of paclitaxel in the micelles at pH 7.4 was substantially increased by interfacial cross-linking, while the release of the drug was triggered at acidic condition (pH 5.0, pH of late endosomes and lysosomes).

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acsbiomaterials.5b00006.

    • Characterizations of the synthesized polymers by 1H NMR and GPC, complete signal assignment of 1H NMR spectrum of the triblock copolymer, 1H NMR characterization of mPEG-b-p(HPMAm-Bz-co-HPMAm-Lac) before and after incubation with ADH, determination of the CMT of p(HPMAm)-b-p(AMPO)-b-p(HPMAm-Bz-co-HPMAm-Lac), and procedure of the in vitro cytotoxicity studies (PDF)

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    This article is cited by 47 publications.

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    ACS Biomaterials Science & Engineering

    Cite this: ACS Biomater. Sci. Eng. 2015, 1, 6, 393–404
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acsbiomaterials.5b00006
    Published April 29, 2015
    Copyright © 2015 American Chemical Society
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