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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...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7570625/ https://www.ncbi.nlm.nih.gov/pubmed/32899627 http://dx.doi.org/10.3390/molecules25184037 |
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author | Wang, Xinli Wang, Liye Xie, Lijun Xie, Zuoxu Li, Li Bui, Dinh Yin, Taijun Gao, Song Hu, Ming |
author_facet | Wang, Xinli Wang, Liye Xie, Lijun Xie, Zuoxu Li, Li Bui, Dinh Yin, Taijun Gao, Song Hu, Ming |
author_sort | Wang, Xinli |
collection | PubMed |
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. |
format | Online Article Text |
id | pubmed-7570625 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-75706252020-10-28 Design and Synthesis of a Novel NIR Celecoxib-Based Fluorescent Probe for Cyclooxygenase-2 Targeted Bioimaging in Tumor Cells Wang, Xinli Wang, Liye Xie, Lijun Xie, Zuoxu Li, Li Bui, Dinh Yin, Taijun Gao, Song Hu, Ming Molecules Communication 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. MDPI 2020-09-04 /pmc/articles/PMC7570625/ /pubmed/32899627 http://dx.doi.org/10.3390/molecules25184037 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Communication Wang, Xinli Wang, Liye Xie, Lijun Xie, Zuoxu Li, Li Bui, Dinh Yin, Taijun Gao, Song Hu, Ming Design and Synthesis of a Novel NIR Celecoxib-Based Fluorescent Probe for Cyclooxygenase-2 Targeted Bioimaging in Tumor Cells |
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 | Communication |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7570625/ https://www.ncbi.nlm.nih.gov/pubmed/32899627 http://dx.doi.org/10.3390/molecules25184037 |
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