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Updated: Nov 4, 2025
Quantitation of Intra-peritoneal Ovarian Cancer Metastasis
Published on: July 18, 2016
Development of Fluorescence Imaging Probes for Labeling COX-1 in Live Ovarian Cancer Cells
Jatinder Kaur1,2, Atul Bhardwaj1,2, Frank Wuest1,2,3
1Department of Oncology, University of Alberta, 11560 University Avenue, Edmonton, Alberta T6G 1Z2, Canada.
Abstract:
Recent experimental evidence demonstrated an aberrant overexpression of cyclooxygenase-1 (COX-1) in various cancers, which has stimulated the development of COX-1-selective inhibitors as promising anticancer drugs and cancer imaging agents. Herein we describe the synthesis and validation of 3-(furan-2-yl)-N-aryl 5-amino-pyrazoles as a novel class of COX-1 inhibitors, including molecular docking studies. Among all tested compounds, 4-(5-azido-3-(furan-2-yl)-1H-pyrazol-1-yl)benzoic 17 displayed a favorable COX-1 inhibition and selectivity profile (COX-1 IC50 = 0.1 μM, SI >1000 over COX-2). Compound 17 was selected as a lead structure for developing the novel COX-1-selective fluorescent probe 22. Fluorescent probe 22 was prepared via click chemistry by installing a nitro-benzoxadiazole motif as a fluorophore into the 3-(furan-2-yl)-N-aryl 5-amino-pyrazole scaffold. Fluorescence probe 22 was tested in ovarian cancer cell line OVCAR-3, confirming its usefulness for targeting and visualizing COX-1 in living cells with confocal microscopy.
Insights
Researchers developed novel cyclooxygenase-1 (COX-1) inhibitors, including a fluorescent probe. This probe effectively targets and visualizes COX-1 in ovarian cancer cells, showing promise for cancer imaging.
Area of Science:
- Medicinal Chemistry
- Chemical Biology
- Cancer Research
Background:
- Aberrant cyclooxygenase-1 (COX-1) overexpression is observed in various cancers.
- COX-1 selective inhibitors are being developed as potential anticancer drugs and imaging agents.
Purpose of the Study:
- To synthesize and validate a novel class of 3-(furan-2-yl)-N-aryl 5-amino-pyrazoles as COX-1 inhibitors.
- To develop a COX-1-selective fluorescent probe for visualizing COX-1 in living cancer cells.
Main Methods:
- Synthesis of novel pyrazole derivatives.
- In vitro COX-1 inhibition and selectivity assays.
- Molecular docking studies.
- Click chemistry for fluorescent probe synthesis.
- Confocal microscopy imaging in ovarian cancer cells (OVCAR-3).
Main Results:
- Compound 17 demonstrated potent and selective COX-1 inhibition (IC50 = 0.1 μM, SI >1000).
- A novel fluorescent probe (22) was synthesized using compound 17 as a lead structure.
- Fluorescent probe 22 successfully targeted and visualized COX-1 in OVCAR-3 cells.
Conclusions:
- 3-(furan-2-yl)-N-aryl 5-amino-pyrazoles represent a promising class of COX-1 inhibitors.
- The developed fluorescent probe is effective for visualizing COX-1 in living cancer cells.
- This work supports the development of COX-1-targeted anticancer therapeutics and imaging agents.
