Reengineered tricyclic anti-cancer agents

Bioorg Med Chem. 2015 Oct 1;23(19):6528-34. doi: 10.1016/j.bmc.2015.07.007. Epub 2015 Sep 11.

Abstract

The phenothiazine and dibenzazepine tricyclics are potent neurotropic drugs with a documented but underutilized anti-cancer side effect. Reengineering these agents (TFP, CPZ, CIP) by replacing the basic amine with a neutral polar functional group (e.g., RTC-1, RTC-2) abrogated their CNS effects as demonstrated by in vitro pharmacological assays and in vivo behavioral models. Further optimization generated several phenothiazines and dibenzazepines with improved anti-cancer potency, exemplified by RTC-5. This new lead demonstrated efficacy against a xenograft model of an EGFR driven cancer without the neurotropic effects exhibited by the parent molecules. Its effects were attributed to concomitant negative regulation of PI3K-AKT and RAS-ERK signaling.

Keywords: Clomipramine; Dibenzazepine; Neuroleptic; Phenothiazine; Tricyclic.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Antineoplastic Agents / therapeutic use
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Dibenzazepines / chemistry
  • Heterocyclic Compounds, 3-Ring / chemistry*
  • Heterocyclic Compounds, 3-Ring / pharmacology
  • Heterocyclic Compounds, 3-Ring / therapeutic use
  • Humans
  • Mice
  • Neoplasms / drug therapy
  • Neoplasms / metabolism
  • Phenothiazines / chemistry
  • Phosphatidylinositol 3-Kinases / metabolism
  • Proto-Oncogene Proteins c-akt / metabolism
  • Signal Transduction / drug effects
  • Transplantation, Heterologous
  • Vesicular Monoamine Transport Proteins / antagonists & inhibitors
  • Vesicular Monoamine Transport Proteins / metabolism

Substances

  • Antineoplastic Agents
  • Dibenzazepines
  • Heterocyclic Compounds, 3-Ring
  • Phenothiazines
  • Vesicular Monoamine Transport Proteins
  • Phosphatidylinositol 3-Kinases
  • Proto-Oncogene Proteins c-akt
  • phenothiazine
  • dibenzazepine