The Mechanochemical Release of Naphthalimide Fluorophores fromβ-Carbonate andβ-Carbamate Disulfide-Centered Polymers  

作　　者：Zhiyuan Shi Qingchuan Song Robert Göstl Andreas Herrmann 

机构地区：[1]DWI—Leibniz Institute for Interactive Materials,Aachen 52056 [2]Institute of Technical and Macromolecular Chemistry,RWTH Aachen University,Aachen 52074 [3]Department I of Internal Medicine,University Hospital of Cologne,Cologne 50937 [4]Zernike Institute for Advanced Materials,University of Groningen,9747 AG Groningen

出　　处：《CCS Chemistry》2021年第11期2333-2344,共12页中国化学会会刊（英文）

基　　金：supported by the European Union(European Research Council Advanced Grant SUPRABIOTICS no.694610);R.G.is grateful for support from a Freigeist Fellowship of the Volkswagen Foundation(no.92888);Parts of the analytical investigations were performed at the Center for Chemical Polymer Technology(CPT),supported by the European Commission and the Federal State of North Rhine-Westphalia(no.300088302).

摘　　要：The covalent attachment of cargo molecules(e.g.,drugs and fluorophores)inβ-position to a disulfide moiety through carbamate and carbonate bonds finds many applications in responsive release systems.Recently,we showed that the combination of this release process with polymer mechanochemistry-induced disulfide scission enabled the remote-controlled release of small molecule drugs and fluorophores from their inactive parent macromolecules using ultrasound.The nature of the linker bond largely governed the subsequent release kinetics,an aspect that has not been investigated so far.To compare the differences,we here employ disulfide-centered polymers releasing either hydroxyl-or amino-naphthalimides from their respectiveβ-carbonate or-carbamate linkers by forceinduced intramolecular 5-exo-trig cyclization.We present the synthesis,characterization,and cell imaging evaluation of three naphthalimides featuring colorimetric and green fluorescence turn-on upon release,allowing monitoring of the release process.We believe that the insights gained from these experiments would advance the tailoring of release rates for force-induced pharmacotherapy.

关 键 词：MECHANOCHEMISTRY POLYMERS drug delivery bioimaging sonopharmacology 

分 类 号：O62[理学—有机化学]