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Systematic Screening of Different Polyglycerin‐Based Dienophile Macromonomers for Efficient Nanogel Formation through IEDDA Inverse Nanoprecipitation
Author(s) -
Oehrl Alexander,
Schötz Sebastian,
Haag Rainer
Publication year - 2020
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201900510
Subject(s) - click chemistry , cycloaddition , nanogel , bioorthogonal chemistry , chemistry , polymer chemistry , drug delivery , organic chemistry , catalysis
Abstract Alternatives for strain‐promoted azide–alkyne cycloaddition (SPAAC) chemistries are needed because of the employment of expensive and not easily scalable precursors such as bicyclo[6.1.0]non‐4‐yne (BCN). Inverse electron demand Diels Alder (iEDDA)‐based click chemistries, using dienophiles and tetrazines, offer a more bioorthogonal and faster toolbox, especially in the biomedical field. Here, the straightforward synthesis of dendritic polyglycerin dienophiles (dPG‐dienophiles) and dPG‐methyl‐tetrazine (dPG‐metTet) as macromonomers for a fast, stable, and scalable nanogel formation by inverse nanoprecipitation is reported. Nanogel size–influencing parameters are screened such as macromonomer concentration and water‐to‐acetone ratio are screened. dPG‐norbonene and dPG‐cyclopropene show fast and stable nanogel formation in the size range of 40–200 nm and are thus used for the coprecipitation of the model protein myoglobin. High encapsulation efficiencies of more than 70% at a 5 wt% feed ratio are obtained in both cases, showing the suitability of the mild gelation chemistry for the encapsulation of small proteins.