New Insights into Tolytoxin Effect in Human Cancer Cells: Apoptosis Induction and the Relevance of Hydroxyl Substitution of Its Macrolide Cycle on Compound Potency

Chembiochem. 2022 Jan 5;23(1):e202100489. doi: 10.1002/cbic.202100489. Epub 2021 Dec 9.

Abstract

Scytophycins, including tolytoxin, represent a class of actin disrupting macrolides with strong antiproliferative effects on human cells. Despite intense research, little attention has been paid to scytophycin-induced cell death or the structural features affecting its potency. We show that tolytoxin and its natural analogue, 7-O-methylscytophycin B, lacking the hydroxyl substitution in its macrolactone ring, differ substantially in their cytotoxic effect. Both compounds increase the level of caspases 3/7, which are the main executioner proteases during apoptosis, in HeLa wild-type (WT) cells. However, no caspase activity was detected in HeLa cells lacking Bax/Bak proteins crucial for caspase activation via the mitochondrial pathway. Obtained data strongly suggests that scytophycins are capable of inducing mitochondria-dependent apoptosis. These findings encourage further research in structure-activity relationships in scytophycins and highlight the potential of these compounds in targeted drug delivery.

Keywords: actin disruption; apoptosis; cancer; scytophycines; tolytoxin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Apoptosis / drug effects*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Screening Assays, Antitumor
  • Humans
  • Hydroxides / chemistry
  • Hydroxides / pharmacology*
  • Macrolides / chemistry
  • Macrolides / pharmacology*
  • Mitochondria / drug effects
  • Mitochondria / metabolism
  • Pyrans / chemistry
  • Pyrans / pharmacology*

Substances

  • Antineoplastic Agents
  • Hydroxides
  • Macrolides
  • Pyrans
  • tolytoxin
  • hydroxide ion