Pyridinium-Substituted Tetraphenylethylenes Functionalized with Alkyl Chains as Autophagy Modulators for Cancer Therapy

Angew Chem Int Ed Engl. 2020 Jun 15;59(25):10042-10051. doi: 10.1002/anie.202001906. Epub 2020 Apr 7.

Abstract

Tuning autophagy in a controlled manner could facilitate cancer therapy but it remains challenging. Pyridinium-substituted tetraphenylethylene salts (PTPE 1-3), able to target mitochondria and disrupt autophagy after forming complexes with albumin, are reported. Mitochondrion affinity and autophagy-inducing activity are improved by prolonging the length of alkyl chains in PTPE 1-3. PTPE 1-3 demonstrate proautophagic activity and a mitophagy blockage effect. Failure of autophagosome-lysosome fusion in downstream autophagy flux results in cancer cell death. Moreover, fast formation of complexes of PTPE 1-3 with albumin in blood can facilitate biomimetic delivery and deep tumor penetration. Efficient tumor accumulation and effective tumor suppression are successfully demonstrated with in vitro and in vivo studies. PTPE 1-3 salts exhibit dual functionality: they target and image mitochondria because of aggregation-induced emission effects and they are promising for cancer therapy.

Keywords: aggregation-induced emission; autophagy; inhibitors; pyridinium-substituted tetraphenylethylenes; tumors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Antineoplastic Agents / therapeutic use
  • Autophagy / drug effects*
  • Cell Fusion
  • Cell Line, Tumor
  • Hep G2 Cells
  • Humans
  • Neoplasms / drug therapy
  • Neoplasms / metabolism
  • Pyridinium Compounds / chemistry*
  • Pyridinium Compounds / pharmacology*
  • Pyridinium Compounds / therapeutic use
  • Stilbenes / chemistry*
  • Stilbenes / pharmacology*
  • Stilbenes / therapeutic use

Substances

  • Antineoplastic Agents
  • Pyridinium Compounds
  • Stilbenes
  • tetraphenylethylene