Recruitment of hexahydroquinoline as anticancer scaffold targeting inhibition of wild and mutants EGFR (EGFRWT, EGFRT790M, and EGFRL858R)

  • J Enzyme Inhib Med Chem. 2023 Dec;38(1):2241674. doi: 10.1080/14756366.2023.2241674.
Mahmoud G Abo Al-Hamd  1 Haytham O Tawfik  1 Omeima Abdullah  2 Koki Yamaguchi  3 Masaharu Sugiura  3 Ahmed B M Mehany  4 Mervat H El-Hamamsy  1 Tarek F El-Moselhy  1
Affiliations
  • 1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Tanta University, Tanta, Egypt.
  • 2. Pharmaceutical Chemistry Department, College of Pharmacy, Umm Al-Qura University, Makkah, Saudi Arabia.
  • 3. Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto, Japan.
  • 4. Zoology Department, Faculty of Science, Al-Azhar University, Cairo, Egypt.
Abstract

Hexahydroquinoline (HHQ) scaffold was constructed and recruited for development of new series of Anticancer agents. Thirty-two new compounds were synthesised where x-ray crystallography was performed to confirm enantiomerism. Thirteen compounds showed moderate to good activity against NCI 60 Cancer cell lines, with GI % mean up to 74% for 10c. Expending erlotinib as a reference drug, target compounds were verified for their inhibiting activities against EGFRWT, EGFRT790M, and EGFRL858R where compound 10d was the best inhibitor with IC50 = 0.097, 0.280, and 0.051 µM, respectively, compared to erlotinib (IC50 = 0.082 µM, 0.342 µM, and 0.055 µM, respectively). Safety profile was validated using normal human lung (IMR-90) cells. 10c and 10d disrupted cell cycle at pre-G1 and G2/M phases in Lung Cancer, HOP-92, and cell line. Molecular docking study was achieved to understand the potential binding interactions and affinities in the active sites of three versions of EGFRs.

Keywords
Hexahydroquinoline; X-ray crystallography; anticancer; molecular docking; wild and mutant EGFR inhibition.
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