Polymeric micelles based on photocleavable linkers tethered with a model drug

Ji Eun Lee, Eungjin Ahn, Jae Min Bak, Seo Hyun Jung, Jong Mok Park, Byeong-Su Kim, Hyung Il Lee

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16 Citations (Scopus)

Abstract

An amphiphilic block copolymer with photocleavable nitrobenzyl moieties in the side chain of the hydrophobic block was successfully synthesized by a combination of atom transfer radical polymerization (ATRP) and the Cu(I)-catalyzed 1,3-dipolar cycloaddition of azide and alkynes. 2-(Trimethylsilyloxy)ethyl methacrylate (HEMATMS) was polymerized from a poly(ethylene oxide) (PEO) macroinitiator via ATRP, leading to a well-defined block copolymer of PEO113-b-PHEMATMS45 with low polydispersity index (PDI = 1.09). After the polymerization, trimethylsilyl (TMS) groups were deprotected and then functionalized in-situ with 3-azidopropionic chloride to yield PEO-b-[2-(1-azidobutyryloxy)ethyl methacrylate] (PEO-b-PAzHEMA). Alkyne-functionalized pyrene with a photocleavable 2-nitrobenzyl moiety was added to the PEO-b-PAzHEMA backbone via click chemistry to produce the desired block copolymer with high fidelity. The resulting block copolymer was self-assembled in water to yield spherical micelles with an average diameter of 60 nm. Upon UV irradiation, 2-nitrobenzyl moieties were selectively cleaved, leading to the release of a model drug, 1-pyrenebutyric acid. Coumarin 102, another model drug that was physically encapsulated in the core of micelles during micellization in water, was also released at the same time. The general strategy presented herein can potentially be utilized for the preparation of polymeric vehicles that are capable of delivering multiple therapeutics under controlled individual release kinetics.

Original languageEnglish
Pages (from-to)1436-1442
Number of pages7
JournalPolymer
Volume55
Issue number6
DOIs
Publication statusPublished - 2014 Mar 24

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

Cite this

Lee, J. E., Ahn, E., Bak, J. M., Jung, S. H., Park, J. M., Kim, B-S., & Lee, H. I. (2014). Polymeric micelles based on photocleavable linkers tethered with a model drug. Polymer, 55(6), 1436-1442. https://doi.org/10.1016/j.polymer.2014.01.026