BIOMAT Database Logo BIOMAT Database Logo

Design, synthesis and biological evaluation of novel imidazole-chalcone derivatives as potential anticancer agents and tubulin polymerization inhibitors. 2021

Sara Rahimzadeh Oskuei, and Salimeh Mirzaei, and Mohammad Reza Jafari-Nik, and Farzin Hadizadeh, and Farhad Eisvand, and Fatemeh Mosaffa, and Razieh Ghodsi
Biotechnology Research Center, Mashhad University of Medical Sciences, Mashhad, Iran; Department of Medicinal Chemistry, School of Pharmacy, Mashhad University of Medical Sciences, Mashhad, Iran.

Novel imidazole-chalcone derivatives were designed and synthesized as tubulin polymerization inhibitors and anticancer agents. The antiproliferative activity of the imidazole-chalcone was assessed on some human cancer cell lines including A549 (adenocarcinoma human alveolar basal epithelial cells), MCF-7 (human breast cancer cells), MCF-7/MX (mitoxantrone resistant human breast cancer cells), and HEPG2 (human hepatocellular carcinoma cells). Generally, the imidazole-chalcone derivatives exhibited more cytotoxicity on A549 cancer cells in comparison to the other three cell lines, among them compounds 9j' and 9g showed significant cytotoxicity with IC50 values ranging from 7.05 to 63.43 μM against all the four human cancer cells. The flow cytometry analysis of A549 cancer cells treated with 9g and 9j' displayed that these compounds induced cell cycle arrest at the G2/M phase at low concentrations and increased the number of apoptotic cells (cells in subG1 phase) at higher concentrations. They have also inhibited tubulin polymerization similar to combretastatin A-4 (CA-4). Annexin V binding staining assay in A549 cancer cells revealed that compound 9j' induced apoptosis (early and late). Finally, molecular docking studies of 9j' into the colchicine-binding site of tubulin presented the probable interactions of these compounds with tubulin.

UI MeSH Term Description Entries
D007093 Imidazoles Compounds containing 1,3-diazole, a five membered aromatic ring containing two nitrogen atoms separated by one of the carbons. Chemically reduced ones include IMIDAZOLINES and IMIDAZOLIDINES. Distinguish from 1,2-diazole (PYRAZOLES).
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D002453 Cell Cycle The complex series of phenomena, occurring between the end of one CELL DIVISION and the end of the next, by which cellular material is duplicated and then divided between two daughter cells. The cell cycle includes INTERPHASE, which includes G0 PHASE; G1 PHASE; S PHASE; and G2 PHASE, and CELL DIVISION PHASE. Cell Division Cycle,Cell Cycles,Cell Division Cycles,Cycle, Cell,Cycle, Cell Division,Cycles, Cell,Cycles, Cell Division,Division Cycle, Cell,Division Cycles, Cell
D002599 Chalcone An aromatic KETONE that forms the core molecule of CHALCONES. Benzalacetophenone,Benzylideneacetophenone,1,3-Diphenyl-2-Propen-1-One,Chalkone,1,3 Diphenyl 2 Propen 1 One
D004305 Dose-Response Relationship, Drug The relationship between the dose of an administered drug and the response of the organism to the drug. Dose Response Relationship, Drug,Dose-Response Relationships, Drug,Drug Dose-Response Relationship,Drug Dose-Response Relationships,Relationship, Drug Dose-Response,Relationships, Drug Dose-Response
D004354 Drug Screening Assays, Antitumor Methods of investigating the effectiveness of anticancer cytotoxic drugs and biologic inhibitors. These include in vitro cell-kill models and cytostatic dye exclusion tests as well as in vivo measurement of tumor growth parameters in laboratory animals. Anticancer Drug Sensitivity Tests,Antitumor Drug Screens,Cancer Drug Tests,Drug Screening Tests, Tumor-Specific,Dye Exclusion Assays, Antitumor,Anti-Cancer Drug Screens,Antitumor Drug Screening Assays,Tumor-Specific Drug Screening Tests,Anti Cancer Drug Screens,Anti-Cancer Drug Screen,Antitumor Drug Screen,Cancer Drug Test,Drug Screen, Anti-Cancer,Drug Screen, Antitumor,Drug Screening Tests, Tumor Specific,Drug Screens, Anti-Cancer,Drug Screens, Antitumor,Drug Test, Cancer,Drug Tests, Cancer,Screen, Anti-Cancer Drug,Screen, Antitumor Drug,Screens, Anti-Cancer Drug,Screens, Antitumor Drug,Test, Cancer Drug,Tests, Cancer Drug,Tumor Specific Drug Screening Tests
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000970 Antineoplastic Agents Substances that inhibit or prevent the proliferation of NEOPLASMS. Anticancer Agent,Antineoplastic,Antineoplastic Agent,Antineoplastic Drug,Antitumor Agent,Antitumor Drug,Cancer Chemotherapy Agent,Cancer Chemotherapy Drug,Anticancer Agents,Antineoplastic Drugs,Antineoplastics,Antitumor Agents,Antitumor Drugs,Cancer Chemotherapy Agents,Cancer Chemotherapy Drugs,Chemotherapeutic Anticancer Agents,Chemotherapeutic Anticancer Drug,Agent, Anticancer,Agent, Antineoplastic,Agent, Antitumor,Agent, Cancer Chemotherapy,Agents, Anticancer,Agents, Antineoplastic,Agents, Antitumor,Agents, Cancer Chemotherapy,Agents, Chemotherapeutic Anticancer,Chemotherapy Agent, Cancer,Chemotherapy Agents, Cancer,Chemotherapy Drug, Cancer,Chemotherapy Drugs, Cancer,Drug, Antineoplastic,Drug, Antitumor,Drug, Cancer Chemotherapy,Drug, Chemotherapeutic Anticancer,Drugs, Antineoplastic,Drugs, Antitumor,Drugs, Cancer Chemotherapy
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D014404 Tubulin A microtubule subunit protein found in large quantities in mammalian brain. It has also been isolated from SPERM FLAGELLUM; CILIA; and other sources. Structurally, the protein is a dimer with a molecular weight of approximately 120,000 and a sedimentation coefficient of 5.8S. It binds to COLCHICINE; VINCRISTINE; and VINBLASTINE. alpha-Tubulin,beta-Tubulin,delta-Tubulin,epsilon-Tubulin,gamma-Tubulin,alpha Tubulin,beta Tubulin,delta Tubulin,epsilon Tubulin,gamma Tubulin

Related Publications

Sara Rahimzadeh Oskuei, and Salimeh Mirzaei, and Mohammad Reza Jafari-Nik, and Farzin Hadizadeh, and Farhad Eisvand, and Fatemeh Mosaffa, and Razieh Ghodsi
Design, Synthesis, and Biological Evaluation of Novel Dihydropyrimidinone Derivatives as Potential Anticancer Agents and Tubulin Polymerization Inhibitors.
January 2023, Assay and drug development technologies,
Sara Rahimzadeh Oskuei, and Salimeh Mirzaei, and Mohammad Reza Jafari-Nik, and Farzin Hadizadeh, and Farhad Eisvand, and Fatemeh Mosaffa, and Razieh Ghodsi
Design, Synthesis, Molecular Docking, and Biological Evaluation of Pyrazole Hybrid Chalcone Conjugates as Potential Anticancer Agents and Tubulin Polymerization Inhibitors.
February 2022, Pharmaceuticals (Basel, Switzerland),
Sara Rahimzadeh Oskuei, and Salimeh Mirzaei, and Mohammad Reza Jafari-Nik, and Farzin Hadizadeh, and Farhad Eisvand, and Fatemeh Mosaffa, and Razieh Ghodsi
Design, synthesis, biological evaluation and molecular docking studies of new chalcone derivatives containing diaryl ether moiety as potential anticancer agents and tubulin polymerization inhibitors.
January 2020, Bioorganic chemistry,
Sara Rahimzadeh Oskuei, and Salimeh Mirzaei, and Mohammad Reza Jafari-Nik, and Farzin Hadizadeh, and Farhad Eisvand, and Fatemeh Mosaffa, and Razieh Ghodsi
Design, synthesis, and biological evaluation of novel 5,6,7-trimethoxy quinolines as potential anticancer agents and tubulin polymerization inhibitors.
December 2020, Iranian journal of basic medical sciences,
Sara Rahimzadeh Oskuei, and Salimeh Mirzaei, and Mohammad Reza Jafari-Nik, and Farzin Hadizadeh, and Farhad Eisvand, and Fatemeh Mosaffa, and Razieh Ghodsi
Design, Synthesis, and Biological Evaluation of Chalcone-Containing Shikonin Derivatives as Inhibitors of Tubulin Polymerization.
March 2017, ChemMedChem,
Sara Rahimzadeh Oskuei, and Salimeh Mirzaei, and Mohammad Reza Jafari-Nik, and Farzin Hadizadeh, and Farhad Eisvand, and Fatemeh Mosaffa, and Razieh Ghodsi
Design, synthesis and biological evaluation of novel thiazole-naphthalene derivatives as potential anticancer agents and tubulin polymerisation inhibitors.
December 2021, Journal of enzyme inhibition and medicinal chemistry,
Sara Rahimzadeh Oskuei, and Salimeh Mirzaei, and Mohammad Reza Jafari-Nik, and Farzin Hadizadeh, and Farhad Eisvand, and Fatemeh Mosaffa, and Razieh Ghodsi
Design, synthesis and biological evaluation of novel acridine and quinoline derivatives as tubulin polymerization inhibitors with anticancer activities.
September 2021, Bioorganic & medicinal chemistry,
Sara Rahimzadeh Oskuei, and Salimeh Mirzaei, and Mohammad Reza Jafari-Nik, and Farzin Hadizadeh, and Farhad Eisvand, and Fatemeh Mosaffa, and Razieh Ghodsi
Design, synthesis and biological evaluation of novel podophyllotoxin derivatives as tubulin-targeting anticancer agents.
December 2024, Pharmaceutical biology,
Sara Rahimzadeh Oskuei, and Salimeh Mirzaei, and Mohammad Reza Jafari-Nik, and Farzin Hadizadeh, and Farhad Eisvand, and Fatemeh Mosaffa, and Razieh Ghodsi
Synthesis and biological evaluation of novel benzo[c]acridine-diones as potential anticancer agents and tubulin polymerization inhibitors.
June 2019, Archiv der Pharmazie,
Sara Rahimzadeh Oskuei, and Salimeh Mirzaei, and Mohammad Reza Jafari-Nik, and Farzin Hadizadeh, and Farhad Eisvand, and Fatemeh Mosaffa, and Razieh Ghodsi
Design, synthesis, and anticancer evaluation of benzophenone derivatives bearing naphthalene moiety as novel tubulin polymerization inhibitors.
November 2020, Bioorganic chemistry,
Copied contents to your clipboard!