Affiliations 

  • 1 Department of Chemistry, Rani Channamma University, Belagavi, Karnataka, India
  • 2 Dr. Prabhakar Kore Basic Science Research Center, KLE Academy of Higher Education and Research, Belagavi, Karnataka, India
  • 3 Department of Physics, B.L.D.E. Association's S.B. Arts and K.C.P. Science College, Vijayapura, Karnataka, India
  • 4 Department of Physics, Rani Channamma University, Belagavi, Karnataka, India
  • 5 X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, George Town, Penang, Malaysia
  • 6 Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Erciyes University, Kayseri, Turkey
J Biomol Struct Dyn, 2023;41(21):11681-11699.
PMID: 36602778 DOI: 10.1080/07391102.2022.2163424

Abstract

A series of novel hydrazone compounds have been synthesized by the condensation of hydrazines and different substituted salicylaldehydes at a molar ratio of 1:1 in one step reaction and characterized by FT-IR, ESI-MS, 1H NMR, and single crystal x-ray diffraction. The crystal structure of the compound shows a trans configuration around the C = N bond and triclinic system with P -1/-p 1. Synthesized compounds were screened for cytotoxicity activities against A375 (melanoma), HT-29 (Colon), and A549 (lung) cancer cell lines. Among them, compound 2 exhibited the highest cytotoxic effect against the A375 cell line (IC50 = 0.30 µM) and HT-29 cell line (1.68 µM), compared to those of apatinib as a reference standard drug (0.28, 1.49 µM, respectively). The cytocompatibility assay on the L929 normal cell line and the hemolysis assay on human RBC were used to validate the non-toxic action. From DFT calculation, the various parameters such as HOMO-LUMO energies, Hirshfeld, and MEP have been studied. Furthermore, in silico molecular docking with three receptors was studied. Among four compounds, compound 2 has the lowest binding energy against cyclin dependent kinase (ΔGb = -9.3 kcal/mol). In addition to this, molecular dynamics (MD) simulation was also performed. Based on this study, these novel hydrazones can be considered a promising anticancer agent due to their potent cytotoxicity activities and computational analysis.Communicated by Ramaswamy H. Sarma.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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