Synthesis of carbon-11 labeled celecoxib derivatives as new candidate PET radioligands for imaging of inflammation

Applied Radiation and Isotopes

Volumn 67, Issue 11, 2009, Pages 2019-2024

  Gao, Mingzhang ^a   Wang, Min ^a   Miller, Kathy D ^a   Hutchins, Gary D ^a   Zheng, Qi Huang ^a  

^a INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Celecoxib derivatives; Cyclooxygenase; Imaging; Inflammation; Positron emission tomography; Radioligands

Indexed keywords

CELECOXIB DERIVATIVES; CYCLOOXYGENASE; IMAGING; INFLAMMATION; RADIOLIGANDS;

ENZYMES; EXTRACTION; IMAGING TECHNIQUES; LABELS; PATHOLOGY; POSITRONS;

POSITRON EMISSION TOMOGRAPHY;

2 [4 [5 (4 METHOXYPHENYL) 3 (TRIFLUOROMETHYL) 1H PYRAZOL 1 YL]PHENYLSULFONAMIDOOXY]ACETIC ACID; 2 [4 [5 (4 TOLYL) 3 (TRIFLUOROMETHYL) 1H PYRAZOL 1 YL]PHENYLSULFONAMIDOOXY]ACETIC ACID; 2 METHYL 2 [4 [5 (4 METHOXYPHENYL) 3 (TRIFLUOROMETHYL) 1H PYRAZOL 1 YL]PHENYLSULFONAMIDOOXY]PROPANOIC ACID; 2 METHYL 2 [4 [5 (4 TOLYL) 3 (TRIFLUOROMETHYL) 1H PYRAZOL 1 YL]PHENYLSULFONAMIDOOXY]PROPANOIC ACID; CARBON 11; CARBON DIOXIDE; CELECOXIB; N (2 CYCLOHEXYLOXY 4 NITROPHENYL)METHANESULFONAMIDE; PROSTAGLANDIN SYNTHASE; RADIOLIGAND; UNCLASSIFIED DRUG;

ARTICLE; BIOMEDICINE; DRUG STRUCTURE; DRUG TARGETING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFLAMMATION; ISOTOPE LABELING; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; METHYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; RADIOCHEMISTRY; SOLID PHASE EXTRACTION; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

ANIMALS; CARBON RADIOISOTOPES; HUMANS; INFLAMMATION; ISOTOPE LABELING; POSITRON-EMISSION TOMOGRAPHY; PYRAZOLES; RADIOLIGAND ASSAY; RADIOPHARMACEUTICALS; SULFONAMIDES;

EID: 69549135103     PISSN: 09698043     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apradiso.2009.07.022     Document Type: Article

References (23)

1. Ahlstrom M.M., Ridderstrom M., Zamora I., and Luthman K. CYP2C9 structure-metabolism relationships: optimizing the metabolic stability of COX-2 inhibitors. J. Med. Chem. 50 (2007) 4444-4452
2. Anzini M., Rovin M., Cappeli A., Vomero S., Manetti F., Botta M., Sautebin L., Rossi A., Pergola C., Ghelardini C., Norcini M., Giordani A., Makovec F., Anzellotti P., Patrignani P., and Biava M. Synthesis, biological evaluation, and enzyme docking simulations of 1,5-diarylpyrrole-3-alkoxyethyl ethers as selective cyclooxygenase-2 inhibitors endowed with anti-inflammatory and antinociceptive activity. J. Med. Chem. 51 (2008) 4476-4481
3. 18F-desbromo-DuP-697 as a PET tracer for cyclooxygenase-2 expression. J. Nucl. Med. 44 (2003) 1700-1706
4. 18F-labeled matrix metalloproteinase-2 inhibitor. Nucl. Med. Biol. 30 (2003) 119-125
5. 3 receptor. Eur. J. Med. Chem. 43 (2008) 1570-1574
6. 11C]methyl triflate. Int. J. Rad. Appl. Instrum. A 43 (1992) 1383-1385
7. Julemont F., de Leval X., Michaux C., Renard J.-F., Winum J.-Y., Montero J.-L., Damas J., Dogne J.-M., and Pirotte B. Design, synthesis, and pharmacological evaluation of pyridinic analogues of nimesulide as cyclooxygenase-2 selective inhibitors. J. Med. Chem. 47 (2004) 6749-6759
8. Kuge Y., Katada Y., Shimonaka S., Temma T., Kimura H., Kiyono Y., Yokota C., Minematsu K., Seki K.-i., Tamaki T., Ohkura K., and Saji H. Synthesis and evaluation of radioiodinated cyclooxygenase-2 inhibitors as potential SPECT tracers for cyclooxygenase-2 expression. Nucl. Med. Biol. 33 (2006) 21-27
9. 6-benzylguanine derivatives. Biomed. Chromatogr. 19 (2005) 379-384
10. 18F-labeled COX-1 and COX-2 inhibitors. J. Nucl. Med. 43 (2002) 117-124
11. 11C]methyl triflate. Nucl. Med. Biol. 26 (1999) 467-471
12. Mock B.H., Glick-Wilson B.E., Zheng Q.-H., and DeGrado T.R. Automated measurement of specific activity of radiolabeled ligands during synthesis. J. Labelled Compd. Radiopharm. 48 (2005) S224
13. 11C-radio-synthesis system. J. Labelled Compd. Radiopharm. 48 (2005) S225
14. 11C]celecoxib: a potential PET probe for imaging COX-2 expression. J. Labelled Compd. Radiopharm. 48 (2005) 887-895
15. 18F]-4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide as a PET imaging probe for COX-2 expression. Bioorg. Med. Chem. 15 (2007) 1802-1807
16. Szabo G., Fischer J., Kis-Varga A., and Gyires K. New celecoxib derivatives as anti-inflammatory agents. J. Med. Chem. 51 (2008) 142-147
17. Wang M., Lacy G., Gao M., Miller K.D., Sledge G.W., and Zheng Q.-H. Synthesis of carbon-11 labeled sulfonanilide analogues as new potential PET agents for imaging of aromatase in breast cancer. Bioorg. Med. Chem. Lett. 17 (2007) 332-336
18. 18F]fluoroiodobenzene as radiotracers for positron emission tomography (PET). Org. Biomol. Chem. 3 (2005) 503-507
19. 11C]β-CFT. Nucl. Med. Biol. 36 (2009) 11-16
20. 11C]β-CIT labeled at nitrogen or oxygen positions. Nucl. Med. Biol. 23 (1996) 981-986
21. 11C]methyl ester. Nucl. Med. Biol. 30 (2003) 753-760
22. Zheng Q.-H., and Mock B.H. Purification of carbon-11 PET radiotracers from unlabeled precursors by preparative HPLC and SPE. Biomed. Chromatogr. 19 (2005) 671-676
23. 18F]hemicholinium-3. Bioorg. Med. Chem. Lett. 17 (2007) 2220-2224