Novel series of 6-(2-substitutedacetamido)-4-anilinoquinazolines as EGFR-ERK signal transduction inhibitors in MCF-7 breast cancer cells

Rania S.M. Ismail, Sahar M. Abou-Seri, Wagdy M. Eldehna, Nasser S.M. Ismail, Sara M. Elgazwi, Hazem A. Ghabbour, Mahmoud Salama Ahmed, Fathi T. Halaweish, Dalal A. Abou El Ella

Research output: Contribution to journalArticlepeer-review

42 Scopus citations

Abstract

Epidermal growth factor receptor (EGFR) signaling pathway has been previously investigated for its significant role in the progression of different types of malignant tumors, where development of small molecules targeting EGFR is well known strategy for design of antitumor agents. Herein, we report the design and synthesis of two series of 6-(2-substitutedacetamido)-4-anilinoquinazolines (6a-x and 13a-d) as EGFR inhibitors. All the newly synthesized quinazoline derivatives were in vitro evaluated for their anti-proliferative activity towards MCF-7 (Breast Cancer) and HepG2 (Hepatocellular carcinoma) cell lines. In particular, compound 6n showed significant inhibitory activity against MCF-7 and HepG2 cell lines (IC50 = 3 and 16 μM, respectively), compared to that of Erlotinib (IC50 = 20 and 25 μM, respectively). Western blotting of 6n at MCF-7 cell line revealed the dual inhibitory activity of 6n towards diminishing the phosphorylated levels for EGFR and ERK. Also, ELISA assay confirmed the anti-EGFR activity of compound 6n (IC50 = 0.037 μM). Finally, a molecular docking study showed the potential binding mode of 6n within the ATP catalytic binding site of EGFR, exhibiting similar binding mode to EGFR inhibitor Erlotinib.

Original languageEnglish (US)
Pages (from-to)782-796
Number of pages15
JournalEuropean Journal of Medicinal Chemistry
Volume155
DOIs
StatePublished - Jul 15 2018
Externally publishedYes

Keywords

  • Anilinoquinazolines
  • Docking
  • EGFR
  • ERK
  • Synthesis

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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