Singlet oxygen-responsive micelles for enhanced photodynamic therapy

J Control Release. 2017 Aug 28:260:12-21. doi: 10.1016/j.jconrel.2017.05.025. Epub 2017 May 17.

Abstract

Photodynamic therapy (PDT) efficacy is limited by the very short half-life and limited diffusion radius of singlet oxygen (1O2). We report a 1O2-responsive micellar nanoplatform subject to considerable size-expansion upon light triggering to facilitate on-demand release of photosensitizers. Imidazole, a well-known 1O2 scavenger, was incorporated in the hydrophobic core of amphiphilic copolymer micelles, and was used to coordinate with biocompatible Zn2+ and encapsulate the photosensitizer chlorin e6 (Ce6). The micelles are highly sensitive to light irradiation: 1O2 triggering induced dramatic particle size expansion due to the conversion of imidazole to hydrophilic urea, resulting in instantaneous release of Ce6 and rapid intracellular distribution. This 1O2-responsive, size-expandable nanosystem delivered substantially more Ce6 to tumor sites as compared to free Ce6, and exhibited improved anti-tumor efficacy in vivo in 4T1 tumor-bearing mice. This work opens new avenues of particle expansion-induced PDT enhancement by controlled imidazole chemistry.

Keywords: Drug delivery; Imidazole; Micelles; Photodynamic therapy; Singlet oxygen-responsive.

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Chlorophyllides
  • Drug Carriers / administration & dosage*
  • Drug Carriers / chemistry
  • Drug Carriers / pharmacokinetics
  • Drug Liberation
  • Female
  • Imidazoles / administration & dosage*
  • Imidazoles / pharmacokinetics
  • Light
  • Mice, Inbred BALB C
  • Micelles*
  • Neoplasms / drug therapy
  • Neoplasms / metabolism
  • Neoplasms / pathology
  • Photochemotherapy*
  • Photosensitizing Agents / administration & dosage*
  • Photosensitizing Agents / chemistry
  • Photosensitizing Agents / pharmacokinetics
  • Porphyrins / administration & dosage*
  • Porphyrins / chemistry
  • Porphyrins / pharmacokinetics
  • Singlet Oxygen / metabolism*

Substances

  • Chlorophyllides
  • Drug Carriers
  • Imidazoles
  • Micelles
  • Photosensitizing Agents
  • Porphyrins
  • Singlet Oxygen
  • phytochlorin
  • imidazole