Structure-Based Design of a Selective Class I Histone Deacetylase (HDAC) Near-Infrared (NIR) Probe for Epigenetic Regulation Detection in Triple-Negative Breast Cancer (TNBC)

J Med Chem. 2021 Apr 8;64(7):4020-4033. doi: 10.1021/acs.jmedchem.0c02161. Epub 2021 Mar 22.

Abstract

Abnormally high levels of class I histone deacetylases (HDACs) are associated with triple-negative breast cancer (TNBC) proliferation, malignant transformation, and poor prognosis of patients. Herein, we report a near-infrared imaging probe for TNBC detection via visualizing class I HDACs. Conjugating Cy5.5 to a cyclic depsipeptide inhibitor, we obtained the probe (20-Cy5.5) that retained desirable class I HDAC affinity and selectivity. Then, this probe could visualize epigenetic changes by class I HDACs in TNBC MDA-MB-231 cells and in xenograft tumor models in real time. Treatment with suberoylanilide hydroxamic acid (SAHA) significantly reduced the uptake of the probe in tumors, suggesting its potential use in evaluation of therapeutic responses of HDACi-mediated therapy. Moreover, 20-Cy5.5 could detect class I HDAC expression in TNBC lung metastasis. This novel NIR probe that achieves tumor class I HDAC imaging not only leads to a better understanding of epigenetic regulation in tumors but also has great potential for improving the TNBC diagnosis and treatment.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biomarkers, Tumor / analysis
  • Biomarkers, Tumor / metabolism
  • Carbocyanines / chemical synthesis
  • Carbocyanines / pharmacology*
  • Cell Line, Tumor
  • Depsipeptides / chemical synthesis
  • Depsipeptides / pharmacology*
  • Epigenesis, Genetic / physiology*
  • Female
  • Fluorometry
  • Gene Expression Regulation, Neoplastic / physiology
  • Heterografts / metabolism
  • Histone Deacetylase Inhibitors / chemical synthesis
  • Histone Deacetylase Inhibitors / pharmacology*
  • Histone Deacetylases / analysis
  • Histone Deacetylases / metabolism*
  • Humans
  • Lung Neoplasms / metabolism
  • Lung Neoplasms / secondary
  • Mice
  • Mice, Nude
  • Triple Negative Breast Neoplasms / metabolism*
  • Triple Negative Breast Neoplasms / pathology
  • Vorinostat / pharmacology

Substances

  • Biomarkers, Tumor
  • CY5.5 cyanine dye
  • Carbocyanines
  • Depsipeptides
  • Histone Deacetylase Inhibitors
  • Vorinostat
  • Histone Deacetylases