Fluorophore-labeled cyclooxygenase-2 inhibitors for the imaging of cyclooxygenase-2 overexpression in cancer: synthesis and biological studies
- PMID: 24376205
- DOI: 10.1002/cmdc.201300355
Fluorophore-labeled cyclooxygenase-2 inhibitors for the imaging of cyclooxygenase-2 overexpression in cancer: synthesis and biological studies
Abstract
A group of cyclooxygenase-2 (COX-2)-specific fluorescent cancer biomarkers were synthesized by linking the anti-inflammatory drugs ibuprofen, (S)-naproxen, and celecoxib to the 7-nitrobenzofurazan (NBD) fluorophore. In vitro COX-1/COX-2 inhibition studies indicated that all of these fluorescent conjugates are COX-2 inhibitors (IC₅₀ range: 0.19-23.0 μM) with an appreciable COX-2 selectivity index (SI≥4.3-444). In this study the celecoxib-NBD conjugate N-(2-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)ethyl)-4-(5-(p-tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide, which displayed the highest COX-2 inhibitory potency and selectivity (COX-2 IC₅₀ =0.19 μM; SI=443.6), was identified as an impending COX-2-specific biomarker for the fluorescence imaging of cancer using a COX-2-expressing human colon cancer cell line (HCA-7).
Keywords: cancer; cyclooxygenases; enzymes; fluorescence; inhibitors; medicinal chemistry.
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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