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Fluorophore-labeled cyclooxygenase-2 inhibitors for the imaging of cyclooxygenase-2 overexpression in cancer: synthesis and biological studies.
- Source :
-
ChemMedChem [ChemMedChem] 2014 Jan; Vol. 9 (1), pp. 109-16, 240. Date of Electronic Publication: 2013 Oct 31. - Publication Year :
- 2014
-
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).<br /> (Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)
- Subjects :
- 4-Chloro-7-nitrobenzofurazan analogs & derivatives
4-Chloro-7-nitrobenzofurazan chemistry
Anti-Inflammatory Agents, Non-Steroidal chemistry
Celecoxib analogs & derivatives
Celecoxib chemistry
Cell Line, Tumor
Colonic Neoplasms metabolism
Colonic Neoplasms pathology
Cyclooxygenase 1 chemistry
Cyclooxygenase 1 metabolism
Cyclooxygenase 2 chemistry
Cyclooxygenase 2 Inhibitors chemistry
Cyclooxygenase 2 Inhibitors metabolism
Cyclooxygenase Inhibitors chemical synthesis
Cyclooxygenase Inhibitors chemistry
Cyclooxygenase Inhibitors metabolism
HCT116 Cells
Humans
Ibuprofen chemistry
Microscopy, Confocal
Naproxen chemistry
Protein Binding
Pyrazoles chemistry
Sulfonamides chemistry
Cyclooxygenase 2 metabolism
Cyclooxygenase 2 Inhibitors chemical synthesis
Fluorescent Dyes chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1860-7187
- Volume :
- 9
- Issue :
- 1
- Database :
- MEDLINE
- Journal :
- ChemMedChem
- Publication Type :
- Academic Journal
- Accession number :
- 24376205
- Full Text :
- https://doi.org/10.1002/cmdc.201300355