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Alan O. Burts, Longyan Liao, Ying Y. Lu, David A. Tirrell and Jeremiah A. Johnson Brush-first and Click: Efficient Synthesis of Nanoparticles that Degrade and Release Doxorubicin in Response to Light Photochemistry and Photobiology 90

Article first published online: 25 NOV 2013 | DOI: 10.1111/php.12182

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Brush-first ring-opening metathesis copolymerization of a poly(ethylene glycol) (PEG)-branch-alkyl chloride macromonomer with a photocleavable bis norbornene crosslinker leads to the formation of brush-arm star polymer (BASP) nanostructures with PEG coronas, photocleavable cores and alkyl chloride functionalities. Conversion of these chlorides to azides, followed by copper-catalyzed azide–alkyne ‘click’ conjugation of a caged doxorubicin (DOX)-alkyne derivative, yielded BASPs that simultaneously degrade and release DOX upon exposure to 365 nm light. These materials displayed low toxicity against MCF-7 human cancer cells in the absence of light; irradiation led to IC50 values similar to that of free DOX.

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