Abstract
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 (IC 50 range: 0.19–23.0 μ M ) 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)‐1 H ‐pyrazol‐1‐yl)benzenesulfonamide ( 14 ), which displayed the highest COX‐2 inhibitory potency and selectivity (COX‐2 IC 50 =0.19 μ M ; 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
CyclooxygenaseChemistryCelecoxibFluorophoreConjugateNaproxenIn vitroEnzymeCancerEtodolacFluorescencePharmacologyBiochemistryStereochemistryMedicinePathologyInternal medicine
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Publication Info
- Year
- 2013
- Type
- article
- Volume
- 9
- Issue
- 1
- Pages
- 109-116
- Citations
- 42
- Access
- Closed
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Cite This
Atul Bhardwaj,
Jatinder Kaur,
Frank Wuest
et al.
(2013).
Fluorophore‐Labeled Cyclooxygenase‐2 Inhibitors for the Imaging of Cyclooxygenase‐2 Overexpression in Cancer: Synthesis and Biological Studies.
ChemMedChem
, 9
(1)
, 109-116.
https://doi.org/10.1002/cmdc.201300355
Identifiers
- DOI
- 10.1002/cmdc.201300355