Design of a small molecule against an oncogenic noncoding RNA

Proc Natl Acad Sci U S A. 2016 May 24;113(21):5898-903. doi: 10.1073/pnas.1523975113. Epub 2016 May 11.

Abstract

The design of precision, preclinical therapeutics from sequence is difficult, but advances in this area, particularly those focused on rational design, could quickly transform the sequence of disease-causing gene products into lead modalities. Herein, we describe the use of Inforna, a computational approach that enables the rational design of small molecules targeting RNA to quickly provide a potent modulator of oncogenic microRNA-96 (miR-96). We mined the secondary structure of primary microRNA-96 (pri-miR-96) hairpin precursor against a database of RNA motif-small molecule interactions, which identified modules that bound RNA motifs nearby and in the Drosha processing site. Precise linking of these modules together provided Targaprimir-96 (3), which selectively modulates miR-96 production in cancer cells and triggers apoptosis. Importantly, the compound is ineffective on healthy breast cells, and exogenous overexpression of pri-miR-96 reduced compound potency in breast cancer cells. Chemical Cross-Linking and Isolation by Pull-Down (Chem-CLIP), a small-molecule RNA target validation approach, shows that 3 directly engages pri-miR-96 in breast cancer cells. In vivo, 3 has a favorable pharmacokinetic profile and decreases tumor burden in a mouse model of triple-negative breast cancer. Thus, rational design can quickly produce precision, in vivo bioactive lead small molecules against hard-to-treat cancers by targeting oncogenic noncoding RNAs, advancing a disease-to-gene-to-drug paradigm.

Keywords: RNA; chemistry; drug design; noncoding RNA; nucleic acids.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenocarcinoma / genetics
  • Adenocarcinoma / metabolism
  • Adenocarcinoma / pathology
  • Adenocarcinoma / therapy*
  • Animals
  • Antagomirs / pharmacokinetics
  • Antagomirs / pharmacology*
  • Base Sequence
  • Binding Sites
  • Cell Line, Tumor
  • Drug Design
  • Female
  • Gene Silencing
  • Humans
  • Mice
  • Mice, Inbred NOD
  • Mice, SCID
  • MicroRNAs / antagonists & inhibitors
  • MicroRNAs / genetics*
  • MicroRNAs / metabolism
  • Nucleic Acid Conformation
  • Ribonuclease III / genetics
  • Ribonuclease III / metabolism
  • Signal Transduction
  • Small Molecule Libraries / pharmacokinetics
  • Small Molecule Libraries / pharmacology*
  • Triple Negative Breast Neoplasms / genetics
  • Triple Negative Breast Neoplasms / metabolism
  • Triple Negative Breast Neoplasms / pathology
  • Triple Negative Breast Neoplasms / therapy*
  • Xenograft Model Antitumor Assays

Substances

  • Antagomirs
  • MIRN96 microRNA, human
  • MicroRNAs
  • Small Molecule Libraries
  • DROSHA protein, human
  • Ribonuclease III