International Journal of Chemical and Biochemical Sciences (ISSN 2226-9614)[/vc_column_text][/vc_column][/vc_row]
VOLUME 25(19) (2024)
Design, Synthesis, and Characterization of Novel Azo Dyes Derivatives as Anticancer Agent Targeting Aurora kinase A
Nagham Hammash1, Djamila Ben Hadda2, Amir Balash3, Mustapha Fawaz Chehna1*
1Department Quality Control and Pharmaceutical Chemistry, Faculty of Pharmacy, University of Aleppo, Aleppo, Syria
2Department Quality Control and Pharmaceutical Chemistry, Faculty of Pharmacy, Ebla Private University, Aleppo, Syria
3Department of Pharmaceutical Chemistry, Institute of Pharmacy, University of Marburg, Marburg, Germany
Abstract
Some new azo dye derivatives have been designed for the development of novel kinase inhibitors. A molecular docking study of designed compounds against Aurora kinase A (PDB: 3K5u) was conducted to identify new drug candidates for cancer therapy. The binding free energy calculated by Molegro virtual docker (MVD) to select the most promising results. The corresponding docking score values in Aurora A kinase of compound 4 gave the best docking energy of -123.2 kcal/mol and for the compound 1 gave the docking energy of -88 kcal/mol. Compound 1 gaven bindings to the following amino acids Ala213, Ala273, Lys162, and Asn261 and compound 4 gaven bindings to the following amino acids Ala213, Ala273, Lys162, and Thr217. These bindings were similar to the primary ligand PFQ-1001, which is Ala213 and Ala273. A complex of azo dye derivatives containing sulfonamide with 8- hydroxyquinoline was synthesized by the conventional two-step method of formation of diazonium moiety and formation of azo dyes. Compound 1 was synthesized from a sulfonamide-containing azo dye derivatives with 8-hydroxyquinoline by a conventional two-step method. The first step is the formation of diazonium ion from a primary aromatic amine compound in acidic nitric acid medium at zero temperature. The second step is the reaction of diazonium ion with 8-hydroxyquinoline compound which has an aromatic ring with a electron donating group (OH) at the para position which facilitates the condensation of the two compounds and the formation of azo groups.The structure of the synthesized compound was well determined by mass spectrometry (MS), infrared spectroscopy (IR), 1H nuclear magnetic resonance (1H NMR), 13C nuclear magnetic resonance (13C NMR), and elemental analysis.
Keywords: cancer, anticancer, sulfonamide, 8- hydroxyl quinolone, azo dyes, Molegro virtual docker.
Full length article – PDF;*Corresponding Author, e-mail: mf.chehna@gmail.com; pharmacist.nagham@gmail.com Doi # https://doi.org/10.62877/120-IJCBS-24-25-19-120