Shell-Sheddable Poly(N-2-hydroxypropyl methacrylamide) Polymeric Micelles for Dual-Sensitive Release of Doxorubicin

Macromol Rapid Commun. 2018 Oct;39(20):e1800139. doi: 10.1002/marc.201800139. Epub 2018 May 16.

Abstract

Poly(ethylene glycol) (PEG) shell-sheddable micelles are proved to be effective tools for rapid intracellular drug delivery. However, some adverse factors, such as the potential immunogenicity and the accelerated blood clearance, might be accompanied with the traditional PEG sheddable micelles. Here, a poly(N-2-hydroxypropyl methacrylamide) (PHPMA) sheddable block copolymer containing disulfide bonds on the main chain is prepared to form pH- and reduction-dual-responsive micelles. The most optimal synthetic route of the block copolymer is selected from three potential pathways. Doxorubicin is loaded via an acid-labile hydrazone bond to achieve high drug loading content and to prevent premature drug release. As expected, as-prepared shell-sheddable micelles exhibit faster intracellular drug release and more satisfactory in vitro anticancer efficacy than the nonsheddable counterpart did. This design provides a feasible guideline for the efficient synthesis of similar shell-sheddable micelles consisting of PHPMA coatings.

Keywords: drug delivery; micelles; pH-sensitive; reduction-sensitive; shell-sheddable.

MeSH terms

  • Cell Survival / drug effects
  • Disulfides / chemistry
  • Doxorubicin / chemistry*
  • Doxorubicin / pharmacology
  • Drug Delivery Systems*
  • Drug Liberation
  • HeLa Cells / drug effects
  • Humans
  • Hydrogen-Ion Concentration
  • Methacrylates / chemical synthesis
  • Methacrylates / chemistry
  • Methacrylates / pharmacology
  • Micelles
  • Neoplasms / drug therapy*
  • Polyethylene Glycols / chemistry
  • Polyethylene Glycols / pharmacology
  • Polymers / chemical synthesis*
  • Polymers / chemistry
  • Polymers / pharmacology

Substances

  • Disulfides
  • Methacrylates
  • Micelles
  • Polymers
  • methacryloylglycylglycine-4-nitrophenyl ester
  • Polyethylene Glycols
  • Doxorubicin