Core-clickable PEG-branch-azide bivalent-bottle-brush polymers by ROMP: grafting-through and clicking-to
| Autor: | Jeremiah A. Johnson, Yeon-Hee Lim, Ying Y. Lu, Jeffrey T. Koberstein, David A. Tirrell, M. G. Finn, Nicholas J. Turro, Alan O. Burts, Robert H. Grubbs |
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| Rok vydání: | 2010 |
| Předmět: |
Azides
Ultraviolet Rays Polyethylene glycol macromolecular substances Biochemistry Micelle Catalysis Article Polyethylene Glycols chemistry.chemical_compound Colloid and Surface Chemistry Polymer chemistry PEG ratio chemistry.chemical_classification technology industry and agriculture General Chemistry ROMP Polymer Macromonomer Nanostructures chemistry Polymerization Doxorubicin Chromatography Gel Azide Copper |
| Zdroj: | Journal of the American Chemical Society. 133(3) |
| ISSN: | 1520-5126 |
| Popis: | The combination of highly efficient polymerizations with modular “click” coupling reactions has enabled the synthesis of wide variety of novel nanoscopic structures. Here we demonstrate the facile synthesis of a new class of clickable, branched nanostructures, polyethylene glycol (PEG)-branch-azide bivalent-brush polymers, facilitated by “graft-through” ring-opening metathesis polymerization (ROMP) of a branched norbornene-PEG-chloride macromonomer followed by halide-azide exchange. The resulting bivalent-brush polymers possess azide groups at the core near a polynorbornene backbone with PEG chains extended into solution; the structure resembles a unimolecular micelle. We demonstrate copper-catalyzed azide-alkyne cycloaddition (CuAAC) “click-to” coupling of a photocleavable doxorubicin (DOX)-alkyne derivative to the azide core. The CuAAC coupling was quantitative across a wide range of nanoscopic sizes (~6 – ~50 nm); UV photolysis of the resulting DOX-loaded materials yielded free DOX that was therapeutically effective against human cancer cells. |
| Databáze: | OpenAIRE |
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