Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 35, Pages 15135-15140Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202004017
Keywords
nanomedicine; polymer-drug conjugates; reaction induced self-assembly; reversible click reaction; self-immolation
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Funding
- NIGMS NIH HHS [R01 GM128181, R35 GM136395] Funding Source: Medline
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Polymer-drug conjugates are promising as strategies for drug delivery, because of their high drug loading capacity and low premature release profile. However, the preparation of these conjugates is often tedious. In this paper, we report an efficient method for polymer-drug conjugates using an ultrafast and reversible click reaction in a post-polymerization functionalization strategy. The reaction is based on the rapid condensation of boronic acid functionalities with salicylhydroxamates. The polymer, bearing the latter functionality, has been designed such that the reaction with boronic acid bearing drugs induces an in situ self-assembly of the conjugates to form well-defined nanostructures. We show that this method is not only applicable for molecules with an intrinsic boronic acid group, but also for the other molecules that can be linked to aryl boronic acids through a self-immolative linker. The linker has been designed to cause traceless release of the attached drug molecules, the efficiency of which has been demonstrated through intracellular delivery.
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