Design and Synthesis of a Novel NIR Celecoxib-Based Fluorescent Probe for Cyclooxygenase-2 Targeted Bioimaging in Tumor Cells
Cyclooxygenase-2 (COX-2) imaging agents are potent tools for early cancer diagnosis. Almost all of the COX2 imaging agents using celecoxib as backbone were chemically modified in the position of N-atom in the sulfonamide group. Herein, a novel COX-2 probe (CCY-5) with high targeting ability and a ne...
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| Format: | Article |
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MDPI AG
2020-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/18/4037 |
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| author | Xinli Wang Liye Wang Lijun Xie Zuoxu Xie Li Li Dinh Bui Taijun Yin Song Gao Ming Hu |
| author_facet | Xinli Wang Liye Wang Lijun Xie Zuoxu Xie Li Li Dinh Bui Taijun Yin Song Gao Ming Hu |
| author_sort | Xinli Wang |
| collection | DOAJ |
| description | Cyclooxygenase-2 (COX-2) imaging agents are potent tools for early cancer diagnosis. Almost all of the COX2 imaging agents using celecoxib as backbone were chemically modified in the position of N-atom in the sulfonamide group. Herein, a novel COX-2 probe (CCY-5) with high targeting ability and a near-infrared wavelength (achieved by attaching a CY-5 dye on the pyrazole ring of celecoxib using a migration strategy) was evaluated for its ability to probe COX-2 in human cancer cells. CCY-5 is expected to have high binding affinity for COX-2 based on molecular docking and enzyme inhibition assay. Meanwhile, CCY-5 caused stronger fluorescence imaging of COX-2 overexpressing cancer cells (Hela and SCC-9 cells) than that of normal cell lines (RAW 264.7 cells). Lipopolysaccharide (LPS) treated RAW264.7 cells revealed an enhanced fluorescence as LPS was known to induce COX-2 in these cells. In inhibitory studies, a markedly reduced fluorescence intensity was observed in cancer cells, when they were co-treated with a COX-2 inhibitor celecoxib. Therefore, CCY-5 may be a selective bioimaging agent for cancer cells overexpressing COX-2 and could be useful as a good monitoring candidate for effective diagnosis and therapy in cancer treatment. |
| first_indexed | 2024-03-10T16:34:30Z |
| format | Article |
| id | doaj.art-02a955bf8c5543c8bbfcc61ed71fe9ba |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T16:34:30Z |
| publishDate | 2020-09-01 |
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| series | Molecules |
| spelling | doaj.art-02a955bf8c5543c8bbfcc61ed71fe9ba2023-11-20T12:33:12ZengMDPI AGMolecules1420-30492020-09-012518403710.3390/molecules25184037Design and Synthesis of a Novel NIR Celecoxib-Based Fluorescent Probe for Cyclooxygenase-2 Targeted Bioimaging in Tumor CellsXinli Wang0Liye Wang1Lijun Xie2Zuoxu Xie3Li Li4Dinh Bui5Taijun Yin6Song Gao7Ming Hu8Department of Medical Oncology, Fujian Medical University Union Hospital, Fuzhou 350001, Fujian, ChinaDepartment of Pharmacological and Pharmaceutical Sciences, College of Pharmacy, University of 10 Houston, Houston, TX 77204, USADepartment of Pharmacological and Pharmaceutical Sciences, College of Pharmacy, University of 10 Houston, Houston, TX 77204, USADepartment of Pharmacological and Pharmaceutical Sciences, College of Pharmacy, University of 10 Houston, Houston, TX 77204, USADepartment of Pharmacological and Pharmaceutical Sciences, College of Pharmacy, University of 10 Houston, Houston, TX 77204, USADepartment of Pharmacological and Pharmaceutical Sciences, College of Pharmacy, University of 10 Houston, Houston, TX 77204, USADepartment of Pharmacological and Pharmaceutical Sciences, College of Pharmacy, University of 10 Houston, Houston, TX 77204, USADepartment of Pharmacological and Pharmaceutical Sciences, College of Pharmacy, University of 10 Houston, Houston, TX 77204, USADepartment of Pharmacological and Pharmaceutical Sciences, College of Pharmacy, University of 10 Houston, Houston, TX 77204, USACyclooxygenase-2 (COX-2) imaging agents are potent tools for early cancer diagnosis. Almost all of the COX2 imaging agents using celecoxib as backbone were chemically modified in the position of N-atom in the sulfonamide group. Herein, a novel COX-2 probe (CCY-5) with high targeting ability and a near-infrared wavelength (achieved by attaching a CY-5 dye on the pyrazole ring of celecoxib using a migration strategy) was evaluated for its ability to probe COX-2 in human cancer cells. CCY-5 is expected to have high binding affinity for COX-2 based on molecular docking and enzyme inhibition assay. Meanwhile, CCY-5 caused stronger fluorescence imaging of COX-2 overexpressing cancer cells (Hela and SCC-9 cells) than that of normal cell lines (RAW 264.7 cells). Lipopolysaccharide (LPS) treated RAW264.7 cells revealed an enhanced fluorescence as LPS was known to induce COX-2 in these cells. In inhibitory studies, a markedly reduced fluorescence intensity was observed in cancer cells, when they were co-treated with a COX-2 inhibitor celecoxib. Therefore, CCY-5 may be a selective bioimaging agent for cancer cells overexpressing COX-2 and could be useful as a good monitoring candidate for effective diagnosis and therapy in cancer treatment.https://www.mdpi.com/1420-3049/25/18/4037COX-2celecoxibCY-5probecancer |
| spellingShingle | Xinli Wang Liye Wang Lijun Xie Zuoxu Xie Li Li Dinh Bui Taijun Yin Song Gao Ming Hu Design and Synthesis of a Novel NIR Celecoxib-Based Fluorescent Probe for Cyclooxygenase-2 Targeted Bioimaging in Tumor Cells Molecules COX-2 celecoxib CY-5 probe cancer |
| title | Design and Synthesis of a Novel NIR Celecoxib-Based Fluorescent Probe for Cyclooxygenase-2 Targeted Bioimaging in Tumor Cells |
| title_full | Design and Synthesis of a Novel NIR Celecoxib-Based Fluorescent Probe for Cyclooxygenase-2 Targeted Bioimaging in Tumor Cells |
| title_fullStr | Design and Synthesis of a Novel NIR Celecoxib-Based Fluorescent Probe for Cyclooxygenase-2 Targeted Bioimaging in Tumor Cells |
| title_full_unstemmed | Design and Synthesis of a Novel NIR Celecoxib-Based Fluorescent Probe for Cyclooxygenase-2 Targeted Bioimaging in Tumor Cells |
| title_short | Design and Synthesis of a Novel NIR Celecoxib-Based Fluorescent Probe for Cyclooxygenase-2 Targeted Bioimaging in Tumor Cells |
| title_sort | design and synthesis of a novel nir celecoxib based fluorescent probe for cyclooxygenase 2 targeted bioimaging in tumor cells |
| topic | COX-2 celecoxib CY-5 probe cancer |
| url | https://www.mdpi.com/1420-3049/25/18/4037 |
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