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Maleimide Functionalized Poly( ε ‐caprolactone)‐ block ‐poly(ethylene glycol) (PCL‐PEG‐MAL): Synthesis, Nanoparticle Formation, and Thiol Conjugation
Author(s) -
Ji Shengxiang,
Zhu Zhengxi,
Hoye Thomas R.,
Macosko Christopher W.
Publication year - 2009
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.200900025
Subject(s) - maleimide , ethylene glycol , polymer chemistry , dispersity , copolymer , peg ratio , caprolactone , chemistry , nanoparticle , materials science , organic chemistry , polymer , nanotechnology , finance , economics
Carboxylic acid terminated poly( ε ‐caprolactone)s (PCL‐COOHs) with narrow polydispersity were synthesized and coupled with poly(ethylene glycol) (HO–PEG–OH) to afford PCL‐PEG–OH copolymers. The hydroxyl groups in the PCL‐PEG–OHs were then converted to maleimide groups to afford maleimide terminated PCL‐PEG‐MALs that contained 70–90% maleimide functionality. Nanoparticles with maleimide functionality on their surfaces were prepared by impingement mixing. Particle sizes and size distributions were determined by dynamic light scattering. Conjugation of reduced glutathione with model maleimides and two MAL‐functional nanoparticles was also demonstrated. The amount of accessible maleimide on the particle surface was measured using Ellman's reagent to range between ≈51–67%.