Scientific Reports (Jul 2017)

Photo-enhanced Aqueous Solubilization of an Azo-compound

  • Minoru Ishikawa,
  • Takuya Ohzono,
  • Takao Yamaguchi,
  • Yasuo Norikane

DOI
https://doi.org/10.1038/s41598-017-06947-w
Journal volume & issue
Vol. 7, no. 1
pp. 1 – 6

Abstract

Read online

Abstract We previously showed that disruption of intermolecular interactions, e.g., by lowering the molecular planarity and/or introducing bent structures, improves the aqueous solubility of compounds, and based upon that work, we hypothesized that azobenzene trans-to-cis photoswitching could also be utilized to enhance the aqueous solubility of compounds. Here, we demonstrate that UV/visible light irradiation can reversibly switch the aqueous solubilization of an anti-cancer candidate drug, a low-molecular-weight kinase inhibitor bearing an azobenzene moiety. The increase of solubilization associated with UV-induced trans-to-cis conversion may have clinical relevance, because the time-scale of thermal cis-to-trans reversion at 37 °C is longer than that of oral absorption.