Self-Assembly Behavior of Emissive Urea Benzene Derivatives Enables Heat-Induced Accumulation in Tumor Tissue

Nano Lett. 2017 Apr 12;17(4):2397-2403. doi: 10.1021/acs.nanolett.6b05371. Epub 2017 Mar 7.

Abstract

In this study we describe the construction of a system composed of thermally responsive molecules that can be induced to accumulate in tumor tissues by heating. EgX molecules consisting of an urea-benzene framework and oligoethylene glycol (OEG) functional groups with an emissive aminoquinoline formed nanoparticles (NPs) ∼10 nm in size at 23 °C with a fluorescence quantum yield of 7-10%. At higher temperatures, additional self-assembly occurred as a result of OEG dehydration, and the NPs grew to over 1000 nm in size; this was accompanied by low critical solution temperature behavior. EgXs accumulated in tumor tissues of mice at a body temperature of around 33-35 °C, an effect that was accelerated by external heating around the tumor to approximately 40 °C as a result of increased particle size and enhanced retention in tissue. These EgX NPs can serve as a tool for in vivo monitoring of tumor progression and response to treatment.

Keywords: LCST; Self-assembly; fluorescence; nanoparticles; tumor imaging.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminoquinolines / chemistry
  • Animals
  • Benzene Derivatives / chemistry*
  • Ethylene Glycol / chemistry
  • Fluorescent Dyes / chemistry*
  • Hot Temperature
  • Mice
  • Mice, Inbred BALB C
  • Nanoparticles / chemistry*
  • Neoplasms / diagnostic imaging*
  • Optical Imaging
  • Particle Size
  • Surface Properties
  • Thermodynamics
  • Tissue Distribution
  • Urea / analogs & derivatives*
  • Urea / chemistry*

Substances

  • Aminoquinolines
  • Benzene Derivatives
  • Fluorescent Dyes
  • Urea
  • Ethylene Glycol