ArticleBioconjugate chemistry2013
Design, synthesis, and structure-activity relationship studies of fluorescent inhibitors of cycloxygenase-2 as targeted optical imaging agents.
Article in Bioconjugate chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed, 79 citations in OpenAlex.
- An Approach Toward Radioiodination and Radiopharmacological Evaluation of a Carborane-Containing Analog of Indomethacin.Molecules (Basel, Switzerland) · 2026Article
- Polymeric Nanoparticles Enable Targeted Visualization of Drug Delivery in Breast Cancer.Molecular pharmaceutics · 2025Article
- Benzo[a]phenoselenazine-based NIR photodynamic therapy for the treatment of COX-2 overexpressing cancer cells.Future medicinal chemistry · 2025Article
- Development and Assessment of 1,5-Diarylpyrazole/Oxime Hybrids Targeting EGFR and JNK-2 as Antiproliferative Agents: A Comprehensive Study through Synthesis, Molecular Docking, and Evaluation.Molecules (Basel, Switzerland) · 2023Article
- Method To Diversify Cyanine Chromophore Functionality Enables Improved Biomolecule Tracking and Intracellular Imaging.Journal of the American Chemical Society · 2023Article
- Design and Development of COX-II Inhibitors: Current Scenario and Future Perspective.ACS omega · 2023Review
- Development of Pluoronic nanoparticles of fluorocoxib A for endoscopic fluorescence imaging of colonic adenomas.Journal of biomedical optics · 2023Article
- Discovery of a Redox-Activatable Chemical Probe for Detection of Cyclooxygenase-2 in Cells and Animals.ACS chemical biology · 2022Article
- Molecular Imaging of Inflammation in Osteoarthritis Using a Water-Soluble Fluorocoxib.ACS medicinal chemistry letters · 2020Article
- Targeted Detection of Cyclooxygenase-1 in Ovarian Cancer.ACS medicinal chemistry letters · 2020Article
- Design and Synthesis of a Novel NIR Celecoxib-Based Fluorescent Probe for Cyclooxygenase-2 Targeted Bioimaging in Tumor Cells.Molecules (Basel, Switzerland) · 2020Article
- An Activity-Based Sensing Approach for the Detection of Cyclooxygenase-2 in Live Cells.Angewandte Chemie (International ed. in English) · 2020Article
- Fluorescent indomethacin-dansyl conjugates utilize the membrane-binding domain of cyclooxygenase-2 to block the opening to the active site.The Journal of biological chemistry · 2019Article
- Aza-BODIPY probe for selective visualization of cyclooxygenase-2 in cancer cells.RSC advances · 2019Article
- Synthesis, Characterization, and Biodistribution of Quantum Dot-Celecoxib Conjugate in Mouse Paw Edema Model.Oxidative medicine and cellular longevity · 2018Article
- Radioiodinated indomethacin amide for molecular imaging of cyclooxygenase-2 expressing tumors.Oncotarget · 2017Article
- Bifunctional conjugates with potent inhibitory activity towards cyclooxygenase and histone deacetylase.Bioorganic & medicinal chemistry · 2017Article
- Antitumor Activity of Cytotoxic Cyclooxygenase-2 Inhibitors.ACS chemical biology · 2016Article
- Development of Antioxidant COX-2 Inhibitors as Radioprotective Agents for Radiation Therapy-A Hypothesis-Driven Review.Antioxidants (Basel, Switzerland) · 2016Review
- A Bright Future for Precision Medicine: Advances in Fluorescent Chemical Probe Design and Their Clinical Application.Cell chemical biology · 2016Review
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Cycloxygenase-2 (COX-2) is an attractive target for molecular imaging because it is an inducible enzyme that is expressed in response to inflammatory and proliferative stimuli. Recently, we reported that conjugation of indomethacin with carboxy-X-rhodamine dyes results in the formation of effective, targeted, optical imaging agents able to detect COX-2 in inflammatory tissues and premalignant and malignant tumors (Uddin et al. Cancer Res. 2010, 70, 3618-3627). The present paper summarizes the details of the structure-activity relationship (SAR) studies performed for lead optimization of these dyes. A wide range of fluorescent conjugates were designed and synthesized, and each of them was tested for the ability to selectively inhibit COX-2 as the purified protein and in human cancer cells. The SAR study revealed that indomethacin conjugates are the best COX-2-targeted agents compared to the other carboxylic acid-containing nonsteroidal anti-inflammatory drugs (NSAIDs) or COX-2-selective inhibitors (COXIBs). An n-butyldiamide linker is optimal for tethering bulky fluorescent functionalities onto the NSAID or COXIB cores. The activity of conjugates also depends on the size, shape, and electronic properties of the organic fluorophores. These reagents are taken up by COX-2-expressing cells in culture, and the uptake is blocked by pretreatment with a COX inhibitor. In in vivo settings, these reagents become highly enriched in COX-2-expressing tumors compared to surrounding normal tissue, and they accumulate selectively in COX-2-expressing tumors as compared with COX-2-negative tumors grown in mice. Thus, COX-2-targeted fluorescent inhibitors are useful for preclinical and clinical detection of lesions containing elevated levels of COX-2.
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Registered trials
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