Design, synthesis, and evaluation of a water-soluble antofine analogue with high antiproliferative and antitumor activity

Bioorg Med Chem. 2013 Feb 15;21(4):1006-17. doi: 10.1016/j.bmc.2012.11.039. Epub 2012 Dec 4.

Abstract

New water soluble antofine C-13a analogues were designed, synthesized, and evaluated for antiproliferative activity against cancer cells. Particularly, (-)-(R)-13a-hydroxymethylantofine ((-)-(R)-4b) demonstrated notable growth inhibition against a panel of human cancer cell lines. This growth inhibition was associated with the arrest of the cell cycle in the G0/G1 phases and suppression of mTOR signaling in human lung A549 cancer cells. Compound (-)-(R)-4b also overcame paclitaxel-resistance in human lung cancer cells (A549-Pa) by suppressing P-glycoprotein expression. Furthermore, compound (-)-(R)-4b significantly inhibited the tumor growth of A549 and A549-Pa xenografts in a nude mouse model, which suggests it is a promising novel antitumor agent with sufficient aqueous solubility.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / therapeutic use
  • Antineoplastic Agents / toxicity
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Design*
  • Drug Evaluation, Preclinical
  • Drug Resistance, Neoplasm / drug effects
  • Drug Screening Assays, Antitumor
  • G1 Phase Cell Cycle Checkpoints / drug effects
  • HCT116 Cells
  • HEK293 Cells
  • Humans
  • Indoles / chemistry*
  • Indoles / therapeutic use
  • Indoles / toxicity
  • Lung Neoplasms / drug therapy
  • Lung Neoplasms / metabolism
  • Lung Neoplasms / pathology
  • Mice
  • Mice, Nude
  • Phenanthrolines / chemistry*
  • Phenanthrolines / therapeutic use
  • Phenanthrolines / toxicity
  • Signal Transduction / drug effects
  • Stereoisomerism
  • TOR Serine-Threonine Kinases / antagonists & inhibitors
  • TOR Serine-Threonine Kinases / metabolism
  • Transplantation, Heterologous
  • Water / chemistry

Substances

  • Antineoplastic Agents
  • Indoles
  • Phenanthrolines
  • antofine
  • Water
  • TOR Serine-Threonine Kinases