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Design, synthesis, and biological evaluation of new celecoxib analogs as apoptosis inducers and cyclooxygenase-2 inhibitors. 2022

Eman F Abdelhaleem, and Asmaa E Kassab, and Hala B El-Nassan, and Omneya M Khalil
Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Cairo University, Cairo, Egypt.

Series of new celecoxib analogs were synthesized to assess their anticancer activity against the MCF-7 cell line. Four compounds, 3a, 3c, 5b, and 5c, showed 1.4-9.2-fold more potent anticancer activity than celecoxib. The antiproliferative activity of the most potent compounds, 3c, 5b, and 5c, seems to be associated well with their ability to induce apoptosis in MCF-7 cells (18-24-fold). This evidence was supported by an increase in the expression of the tumor suppressor gene p53 (4-6-fold), the elevation in the Bax/BCL-2 ratio, and a significant increase in the level of active caspase-7 (4-7-fold). Moreover, compounds 3c and 5c showed significant cyclooxygenase-2 (COX-2) inhibitory activity. They were also docked into the crystal structure of the COX-2 enzyme (PDB ID: 3LN1) to understand their mode of binding.

UI MeSH Term Description Entries
D011720 Pyrazoles Azoles of two nitrogens at the 1,2 positions, next to each other, in contrast with IMIDAZOLES in which they are at the 1,3 positions.
D000068579 Celecoxib A pyrazole derivative and selective CYCLOOXYGENASE 2 INHIBITOR that is used to treat symptoms associated with RHEUMATOID ARTHRITIS; OSTEOARTHRITIS and JUVENILE ARTHRITIS, as well as the management of ACUTE PAIN. 4-(5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide,Celebrex,SC 58635,SC-58635,SC58635
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
D013449 Sulfonamides A group of compounds that contain the structure SO2NH2. Sulfonamide,Sulfonamide Mixture,Sulfonamide Mixtures,Mixture, Sulfonamide,Mixtures, Sulfonamide
D017209 Apoptosis A regulated cell death mechanism characterized by distinctive morphologic changes in the nucleus and cytoplasm, including the endonucleolytic cleavage of genomic DNA, at regularly spaced, internucleosomal sites, i.e., DNA FRAGMENTATION. It is genetically programmed and serves as a balance to mitosis in regulating the size of animal tissues and in mediating pathologic processes associated with tumor growth. Apoptosis, Extrinsic Pathway,Apoptosis, Intrinsic Pathway,Caspase-Dependent Apoptosis,Classic Apoptosis,Classical Apoptosis,Programmed Cell Death,Programmed Cell Death, Type I,Apoptoses, Extrinsic Pathway,Apoptoses, Intrinsic Pathway,Apoptosis, Caspase-Dependent,Apoptosis, Classic,Apoptosis, Classical,Caspase Dependent Apoptosis,Cell Death, Programmed,Classic Apoptoses,Extrinsic Pathway Apoptoses,Extrinsic Pathway Apoptosis,Intrinsic Pathway Apoptoses,Intrinsic Pathway Apoptosis
D045744 Cell Line, Tumor A cell line derived from cultured tumor cells. Tumor Cell Line,Cell Lines, Tumor,Line, Tumor Cell,Lines, Tumor Cell,Tumor Cell Lines
D051546 Cyclooxygenase 2 An inducibly-expressed subtype of prostaglandin-endoperoxide synthase. It plays an important role in many cellular processes and INFLAMMATION. It is the target of COX2 INHIBITORS. COX-2 Prostaglandin Synthase,Cyclo-Oxygenase II,Cyclooxygenase-2,PGHS-2,PTGS2,Prostaglandin H Synthase-2,COX 2 Prostaglandin Synthase,Cyclo Oxygenase II,Prostaglandin H Synthase 2,Prostaglandin Synthase, COX-2,Synthase, COX-2 Prostaglandin
D052246 Cyclooxygenase 2 Inhibitors A subclass of cyclooxygenase inhibitors with specificity for CYCLOOXYGENASE-2. COX-2 Inhibitor,COX2 Inhibitor,Coxib,Cyclooxygenase 2 Inhibitor,Cyclooxygenase-2 Inhibitor,COX-2 Inhibitors,COX2 Inhibitors,Coxibs,Cyclooxygenase-2 Inhibitors,2 Inhibitor, Cyclooxygenase,COX 2 Inhibitor,COX 2 Inhibitors,Inhibitor, COX-2,Inhibitor, COX2,Inhibitor, Cyclooxygenase 2,Inhibitor, Cyclooxygenase-2,Inhibitors, COX-2,Inhibitors, COX2,Inhibitors, Cyclooxygenase 2,Inhibitors, Cyclooxygenase-2

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