Combined inhibition of the EGFR/AKT pathways by a novel conjugate of quinazoline with isothiocyanate

Eur J Med Chem. 2016 Jul 19:117:283-91. doi: 10.1016/j.ejmech.2016.04.002. Epub 2016 Apr 4.

Abstract

Epidermal growth factor receptor inhibitors (EGFR-TKIs) represent a class of compounds widely used in anticancer therapy. An increasing number of studies reports on combination therapies in which the block of the EGFR-TK activity is associated with inhibition of its downstream pathways, as PI3K-Akt. Sulforaphane targets the PI3K-Akt pathway whose dysregulation is implicated in many functions of cancer cells. According to these considerations, a series of multitarget molecules have been designed by combining key structural features derived from an EGFR-TKI, PD168393, and the isothiocyanate sulforaphane. Among the obtained molecules 1-6, compound 6 emerges as a promising lead compound able to exert antiproliferative and proapoptotic effects in A431 epithelial cancer cell line by covalently binding to EGFR-TK, and reducing the phosphorylation of Akt without affecting the total Akt levels.

Keywords: Akt phosphorylation; EGFR-TK inhibitors; Isothiocyanate; Multitarget agents; Sulforaphane.

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Apoptosis / drug effects
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • ErbB Receptors / antagonists & inhibitors*
  • Humans
  • Isothiocyanates / pharmacology*
  • Phosphatidylinositol 3-Kinases
  • Proto-Oncogene Proteins c-akt / antagonists & inhibitors*
  • Quinazolines / pharmacology*
  • Sulfoxides

Substances

  • Antineoplastic Agents
  • Isothiocyanates
  • Quinazolines
  • Sulfoxides
  • ErbB Receptors
  • Proto-Oncogene Proteins c-akt
  • sulforaphane