Exploring the tetrahydroisoquinoline thiohydantoin scaffold blockade the androgen receptor as potent anti-prostate cancer agents

Eur J Med Chem. 2018 Jan 1:143:1325-1344. doi: 10.1016/j.ejmech.2017.10.031. Epub 2017 Oct 14.

Abstract

Prostate cancer (PC) is a major cause of cancer-related male death in worldwide and the identification of new and improved potent anti-PC molecules is constantly required. A novel scaffold of tetrahydroisoquinoline thiohydantoin was rationally designed based on the enzalutamide structures and our pre-work, leading to the discovery of a series of new antiproliferative compounds. Several new analogues displayed improved androgen receptor (AR) antagonistic activity, while maintaining the higher selective toxicity toward LNCaP cells (AR-rich) versus DU145 cells (AR-deficient) compared to enzalutamide. In fact, compound 55 exhibited promising in vitro antitumor activity by impairing AR unclear translocation. More importantly, 55 showed better pharmacokinetic properties compared to the compound 1 reported in our pre-work. These results demonstrate a step towards the development of novel and improved AR antagonists.

Keywords: Androgen receptor; Antagonist; Prostate cancer; Tetrahydroisoquinoline thiohydantoin derivatives.

MeSH terms

  • Androgen Receptor Antagonists / chemistry
  • Androgen Receptor Antagonists / metabolism
  • Androgen Receptor Antagonists / pharmacokinetics
  • Androgen Receptor Antagonists / pharmacology
  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / metabolism
  • Antineoplastic Agents / pharmacokinetics
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Design*
  • Humans
  • Male
  • Molecular Docking Simulation
  • Prostatic Neoplasms / drug therapy
  • Prostatic Neoplasms / pathology*
  • Protein Conformation
  • Rats
  • Receptors, Androgen / chemistry
  • Receptors, Androgen / metabolism*
  • Thiohydantoins / chemistry*
  • Thiohydantoins / metabolism
  • Thiohydantoins / pharmacokinetics
  • Thiohydantoins / pharmacology*

Substances

  • Androgen Receptor Antagonists
  • Antineoplastic Agents
  • Receptors, Androgen
  • Thiohydantoins