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Synthesis of Passerini-3CR Polymers and Assembly into Cytocompatible Polymersomes

Travanut, Alessandra; Monteiro, Patrícia F.; Oelmann, Stefan; Howdle, Steven M.; Grabowska, Anna M.; Clarke, Philip A.; Ritchie, Alison A.; Meier, Michael A.R.; Alexander, Cameron


Alessandra Travanut

Stefan Oelmann

Professor of Cancer Microenvironment

Philip A. Clarke

Alison A. Ritchie

Michael A.R. Meier


© 2020 The Authors. Published by Wiley-VCH GmbH The versatility of the Passerini three component reaction (Passerini-3CR) is herein exploited for the synthesis of an amphiphilic diblock copolymer, which self-assembles into polymersomes. Carboxy-functionalized poly(ethylene glycol) methyl ether is reacted with AB-type bifunctional monomers and tert-butyl isocyanide in a single process via Passerini-3CR. The resultant diblock copolymer (P1) is obtained in good yield and molar mass dispersity and is well tolerated in model cell lines. The Passerini-3CR versatility and reproducibility are shown by the synthesis of P2, P3, and P4 copolymers. The ability of the Passerini P1 polymersomes to incorporate hydrophilic molecules is verified by loading doxorubicin hydrochloride in P1DOX polymersomes. The flexibility of the synthesis is further demonstrated by simple post-functionalization with a dye, Cyanine-5 (Cy5). The obtained P1-Cy5 polymersomes rapidly internalize in 2D cell monolayers and penetrate deep into 3D spheroids of MDA-MB-231 triple-negative breast cancer cells. P1-Cy5 polymersomes injected systemically in healthy mice are well tolerated and no visible adverse effects are seen under the conditions tested. These data demonstrate that new, biodegradable, biocompatible polymersomes having properties suitable for future use in drug delivery can be easily synthesized by the Passerini-3CR.

Journal Article Type Article
Publication Date Aug 16, 2020
Journal Macromolecular Rapid Communications
Print ISSN 1022-1336
Electronic ISSN 1521-3927
Publisher Wiley
Peer Reviewed Peer Reviewed
APA6 Citation Travanut, A., Monteiro, P. F., Oelmann, S., Howdle, S. M., Grabowska, A. M., Clarke, P. A., …Alexander, C. (2020). Synthesis of Passerini-3CR Polymers and Assembly into Cytocompatible Polymersomes. Macromolecular Rapid Communications,
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