Synthesis of click-reactive HPMA copolymers using RAFT polymerization for drug delivery applications

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  • Morten F Ebbesen, Danmark
  • D.H. Schaffert, Danmark
  • Michael L Crowley, Human Metabolome Technologies, Cambridge, USA
  • David Oupický, Department of Pharmaceutical Sciences and Center for Drug Delivery and Nanomedicine, University of Nebraska Medical Center, USA
  • Ken Howard
This study describes a versatile strategy combining reversible addition fragmentation transfer (RAFT) polymerization and click chemistry to synthesize well-defined, reactive copolymers of N-(2-hydroxypropyl)methacrylamide (HPMA) for drug delivery applications. A novel azide containing monomer N-(3-azidopropyl)methacrylamide (AzMA) was synthesized and copolymerized with HPMA using RAFT polymerization to provide p(HPMA-co-AzMA) copolymers with high control of molecular weight (∼10–54 kDa) and polydispersity (≤1.06). The utility of the side-chain azide functionality by Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) was demonstrated by efficient conjugation (up to 92%) of phosphocholine, a near infrared dye, and poly(ethylene glycol) (PEG) with different substitution degrees, either alone or in combination. This study introduces a novel and versatile method to synthesize well-defined click-reactive HPMA copolymers for preparing a panel of bioconjugates with different functionalities needed to systemically evaluate and tune the biological performance of polymer-based drug delivery
OriginalsprogEngelsk
TidsskriftJournal of Polymer Science. Part A, Polymer Chemistry
Vol/bind51
Nummer23
Sider (fra-til)5091-5099
Antal sider9
ISSN0887-624X
DOI
StatusUdgivet - 1 dec. 2013

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