Design, synthesis and biological activity of novel molecules designed to target PARP and DNA

Bioorg Med Chem Lett. 2017 Feb 1;27(3):688-694. doi: 10.1016/j.bmcl.2016.09.054. Epub 2016 Sep 22.

Abstract

In order to enhance the cytotoxic potential of poly(ADP-ribose) polymerase (PARP) inhibitors in BRCA1 or 2 deficient tumours, we designed a series of molecules containing a 1,2,3-triazene moiety tethered to a PARP targeting scaffold. A cell-based selectivity assay involving a BRCA2-deficient Chinese hamster cell line and its corresponding BRCA2 wild type transfectant, was used to predict the PARP targeting potential of the latter agents. The results showed that adding a DNA damaging function to the PARP inhibitors decreased but did not abrogate the selective targeting of the BRCA2-deficient cells. The DNA damaging moiety augmented the potency in BRCA2 deficient cells by 2-20 fold. The most selective dual PARP-DNA targeting agent 14b was found to possess dual DNA and PARP targeting properties.

Keywords: BRCA mutation; Bis-targeting; DNA damage; PARP inhibitors; Synthetic lethality.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • BRCA2 Protein / deficiency
  • BRCA2 Protein / genetics
  • Binding Sites
  • CHO Cells
  • Cricetinae
  • Cricetulus
  • DNA / chemistry
  • DNA / metabolism*
  • DNA Damage / drug effects
  • Drug Design*
  • Enzyme Activation / drug effects
  • Molecular Docking Simulation
  • Poly(ADP-ribose) Polymerase Inhibitors / chemical synthesis*
  • Poly(ADP-ribose) Polymerase Inhibitors / chemistry
  • Poly(ADP-ribose) Polymerase Inhibitors / pharmacology*
  • Poly(ADP-ribose) Polymerases / chemistry
  • Poly(ADP-ribose) Polymerases / metabolism*
  • Protein Structure, Tertiary

Substances

  • BRCA2 Protein
  • Poly(ADP-ribose) Polymerase Inhibitors
  • DNA
  • Poly(ADP-ribose) Polymerases

Grants and funding