Photoactivation of MDM2 Inhibitors: Controlling Protein-Protein Interaction with Light

J Am Chem Soc. 2018 Oct 17;140(41):13136-13141. doi: 10.1021/jacs.8b04870. Epub 2018 Oct 4.

Abstract

Selectivity remains a major challenge in anticancer therapy, which potentially can be overcome by local activation of a cytotoxic drug. Such triggered activation can be obtained through modification of a drug with a photoremovable protecting group (PPG), and subsequent irradiation in the chosen place and time. Herein, the design, synthesis and biological evaluation is described of a photoactivatable MDM2 inhibitor, PPG-idasanutlin, which exerts no functional effect on cellular outgrowth, but allows for the selective, noninvasive activation of antitumor properties upon irradiation visible light, demonstrating activation with micrometer, single cell precision. The generality of this method has been demonstrated by growth inhibition of multiple cancer cell lines showing p53 stabilization and subsequent growth inhibition effects upon irradiation. Light activation to regulate protein-protein interactions between MDM2 and p53 offers exciting opportunities to control a multitude of biological processes and has the potential to circumvent common selectivity issues in antitumor drug development.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Coumarins / chemical synthesis
  • Coumarins / chemistry
  • Coumarins / pharmacology*
  • Coumarins / radiation effects
  • Humans
  • Light
  • Molecular Docking Simulation
  • Protein Binding / drug effects
  • Proto-Oncogene Proteins c-mdm2 / chemistry
  • Proto-Oncogene Proteins c-mdm2 / metabolism*
  • Pyrrolidines / chemical synthesis
  • Pyrrolidines / chemistry
  • Pyrrolidines / pharmacology*
  • Pyrrolidines / radiation effects
  • Transcription Factors / chemistry
  • Transcription Factors / metabolism*
  • Xenopus Proteins / chemistry
  • Xenopus Proteins / metabolism*
  • Xenopus laevis
  • para-Aminobenzoates / chemical synthesis
  • para-Aminobenzoates / chemistry
  • para-Aminobenzoates / pharmacology*
  • para-Aminobenzoates / radiation effects

Substances

  • Coumarins
  • Pyrrolidines
  • RG7388
  • TP53 protein, Xenopus
  • Transcription Factors
  • Xenopus Proteins
  • para-Aminobenzoates
  • MDM2 protein, Xenopus
  • Proto-Oncogene Proteins c-mdm2