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

Johnson, Jeremiah A. and Lu, Ying Y. and Burts, Alan O. and Lim, Yeon-Hee and Finn, M. G. and Koberstein, Jeffrey T. and Turro, Nicholas J. and Tirrell, David A. and Grubbs, Robert H. (2011) Core-Clickable PEG-Branch-Azide Bivalent-Bottle-Brush Polymers by ROMP: Grafting-Through and Clicking-To. Journal of the American Chemical Society, 133 (3). pp. 559-566. ISSN 0002-7863. PMCID PMC3077470. https://resolver.caltech.edu/CaltechAUTHORS:20110321-113913494

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Abstract

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja108441d DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja108441dPublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3077470/PubMed CentralArticle
ORCID:
AuthorORCID
Tirrell, David A.0000-0003-3175-4596
Grubbs, Robert H.0000-0002-0057-7817
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.
Funders:
Funding AgencyGrant Number
NIHR01-GM31332
Caltech Beckman InstituteUNSPECIFIED
NSFDMR-0520565
Issue or Number:3
PubMed Central ID:PMC3077470
Record Number:CaltechAUTHORS:20110321-113913494
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20110321-113913494
Official Citation:Core-Clickable PEG-Branch-Azide Bivalent-Bottle-Brush Polymers by ROMP: Grafting-Through and Clicking-To Jeremiah A. Johnson, Ying Y. Lu, Alan O. Burts, Yeon-Hee Lim, M. G. Finn, Jeffrey T. Koberstein, Nicholas J. Turro, David A. Tirrell, Robert H. Grubbs Journal of the American Chemical Society 2011 133 (3), 559-566
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:23013
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:21 Mar 2011 20:17
Last Modified:03 Oct 2019 02:42

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