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Biocompatible unimolecular micelles obtained via the Passerini reaction as versatile nanocarriers for potential medical applications

Oelmann, Stefan; Travanut, Alessandra; Barther, Dennis; Romero, Manuel; Howdle, Steven M.; Alexander, Cameron; Meier, Michael A.R.

Authors

Stefan Oelmann

Alessandra Travanut ALESSANDRA.TRAVANUT@nottingham.ac.uk

Dennis Barther

Michael A.R. Meier



Abstract

A Passerini three-component polymerization was performed for the synthesis of amphiphilic star-shaped block copolymers with hydrophobic cores and hydrophilic coronae. The degree of polymerization of the hydrophobic core was varied from 5 to 10 repeating units, and the side chain ends were conjugated by performing a Passerini-3CR with PEG-isocyanide and PEG-aldehyde (950 g/mol). The resulting amphiphilic star-shaped block copolymers contained thioether groups, which could be oxidized to sulfones in order to further tune the polarity of the polymer chains. The ability of the amphiphilic copolymers to act as unimolecular micellar encapsulants was tested with the water-insoluble dye Orange II, the water-soluble dye Para Red and the macrolide antibiotic azithromycin. The results showed that the new copolymers were able to retain drug cargo at pH levels corresponding to circulating blood and selectively release therapeutically effective doses of antibiotic as measured by bacterial cell kill. The polymers were also well-tolerated by differentiated THP-1 macrophages in the absence of encapsulated drugs.

Journal Article Type Article
Publication Date Jan 14, 2019
Journal Biomacromolecules
Print ISSN 1525-7797
Electronic ISSN 1526-4602
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 20
Issue 1
Pages 90-101
APA6 Citation Oelmann, S., Travanut, A., Barther, D., Romero, M., Howdle, S. M., Alexander, C., & Meier, M. A. (2019). Biocompatible unimolecular micelles obtained via the Passerini reaction as versatile nanocarriers for potential medical applications. Biomacromolecules, 20(1), 90-101. https://doi.org/10.1021/acs.biomac.8b00592
DOI https://doi.org/10.1021/acs.biomac.8b00592
Publisher URL http://dx.doi.org/10.1021/acs.biomac.8b00592
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingh.../end_user_agreement.pdf

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://eprints.nottingham.ac.uk/end_user_agreement.pdf





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