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Published January 26, 2011 | Accepted Version + Supplemental Material
Journal Article Open

Core-Clickable PEG-Branch-Azide Bivalent-Bottle-Brush Polymers by ROMP: Grafting-Through and Clicking-To


The combination of highly efficient polymerizations with modular "click" coupling reactions has enabled the synthesis of a wide variety of novel nanoscopic tructures. 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 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-alkre 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 (similar to 6-similar to 50 nrn); UV photolysis of the resulting DOX-loaded materials yielded free DOX that was therapeutically effective against human cancer cells.

Additional Information

© 2010 American Chemical Society. Received: September 18, 2010. Article ASAP December 13, 2010. Published In Issue January 26, 2011. We thank Dr. S. Virgil and Mr. S. Presolski for helpful advice. This work was supported by the National Institutes of Health (NIH, R01-GM31332), the Beckman Institute at Caltech (postdoctoral fellowship for J.A.J.), and the MRSEC program of the National Science Foundation (NSF) under Award No. DMR-0520565.

Attached Files

Accepted Version - nihms258485.pdf

Supplemental Material - ja108441d_si_001.pdf


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