Radiotracers for molecular imaging of cyclooxygenase-2 (COX-2) enzyme

Current Medicinal Chemistry

Volumn 20, Issue 35, 2013, Pages 4350-4369

  Tietz, O ^a   Marshall, A ^a   Wuest, M ^a   Wang, M ^a   Wuest, F ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Cyclooxygenase 2; Molecular imaging; Positron emission tomography; Radiotracer; Single photon emission computed tomography

Indexed keywords

1 (4 FLUOROPHENYL) 2 [(4 METHYLSULFONYL)PHENYL]CYCLOPENTENE; 5 (4 FLUOROPHENYL) 1 [(4 METHYLSULFONYL)PHENYL] 3 TRIFLUOROMETHYLPYRAZOLE; 5 BROMO 2 (4 FLUOROPHENYL) 3 (4 METHYLSULFONYLPHENYL)THIOPHENE; CARBON 11; CELECOXIB; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; ETORICOXIB; FLUORINE 18; IMIDAZOLE DERIVATIVE; INDOLE DERIVATIVE; INDOMETACIN; IODINE 123; IODINE 125; LUMIRACOXIB; N (2 CYCLOHEXYLOXY 4 NITROPHENYL)METHANESULFONAMIDE; NITROGEN 13; OXYGEN 15; PROSTACYCLIN; PROSTAGLANDIN; ROFECOXIB; TECHNETIUM 99M; THROMBOXANE; TRACER; VALDECOXIB;

ALZHEIMER DISEASE; ANTIINFLAMMATORY ACTIVITY; ARTICLE; AUTORADIOGRAPHY; BLOOD BRAIN BARRIER; CARDIOTOXICITY; CONTRAST TO NOISE RATIO; DISEASE COURSE; DRUG DESIGN; DRUG DISTRIBUTION; DRUG EXCRETION; DRUG HALF LIFE; DRUG POTENCY; DRUG PURIFICATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG UPTAKE; ELECTROPHILICITY; ENZYME ACTIVITY; FLUORINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; IMAGE ENHANCEMENT; IN VITRO STUDY; IN VIVO STUDY; INFLAMMATION; ISOTOPE LABELING; LIPOPHILICITY; MOLECULAR IMAGING; NONHUMAN; PAIN; PARKINSON DISEASE; POSITRON EMISSION TOMOGRAPHY; PROTEIN EXPRESSION; PROTEIN METHYLATION; RADIOACTIVITY; RADIOCHEMISTRY; RADIOSENSITIZATION; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; SUZUKI REACTION; TUMOR CELL LINE;

ANIMALS; CYCLOOXYGENASE 2; HUMANS; NEOPLASMS; NEURODEGENERATIVE DISEASES; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; TISSUE DISTRIBUTION;

EID: 84887914079     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/09298673113206660260     Document Type: Article

References (95)

1. Warner, T.D.; Mitchell, J.A. Cyclooxygenase-3 (COX-3): Filling in the gaps toward a COX continuum? Proc. Natl. Acad. Sci. U S A, 2002, 99(21), 13371-13373.
2. Kurumbail, R.G.; Kiefer, J.R.; Marnett, L.J. Cyclooxygenase enzymes: Catalysis and inhibition. Curr. Opin. Struct. Biol., 2001, 11(6), 752-760.
3. Luong, C.; Miller, A.; Barnett, J.; Chow, J.; Ramesha, C.; Browner, M.F. Flexibility of the NSAID binding site in the structure of human cyclooxygenase-2. Nat. Struct. Biol., 1996, 3(11), 927-933.
4. Shi, S.; Klotz, U. Clinical use and pharmacological properties of selective COX-2 inhibitors. Eur. J. Clin. Pharmacol., 2008, 64(3), 233-252.
5. DeWitt, D. Cox-2-selective inhibitors: The new super aspirins. Mol. Pharmacol., 1999, 55(4), 625-631.
6. Cannon, C.P.; Cannon, P.J. COX-2 Inhibitors and Cardiovascular Risk. Science, 2012, 336, 1386-1387.
7. Yu, Y.; Ricciotti, E.; Scalia, R.; Tang, S.Y.; Grant, G.; Yu, Z.; Landesberg, G.; Crichton, I.; Wu, W.; Pure, E.; Funk, C.; Fitz-Gerald, G. Vascular COX-2 Modulates Blood Pressure and Thrombosis in Mice. Sci. Transl. Med., 2012, 4(132), 132ra54.
8. Fiorucci, S.; Distrutti, E. COXIBs, CINODs and H2S-Releasing NSAIDs: Current Perspectives in the Development of Safer Non Steroidal Anti-Inflammatory Drugs. Curr. Med. Chem., 2011, 18(23), 3494-3505.
9. Rovati, G.E.; Sala, A.; Capra, V.; Dahlén, S.E.; Folco, G. Dual COXIB/TP antagonists: a possible new twist in NSAID pharmacology and cardiovascular risk. Trends Pharmacol. Sci., 2010, 31(3), 102-107.
10. Scheiman, J.M. Unmet needs in non-steroidal anti-inflammatory drug-induced upper gastrointestinal diseases. Drugs, 2006, 66 Suppl 1, 15-21; discussion 29-33.
11. Seibert, K.; Zhang, Y.; Leahy, K.; Hauser, S.; Masferrer, J.; Perkins, W.; Lee, L.; Isakson, P. Pharmacological and biochemical demonstration of the role of cyclooxygenase 2 in inflammation and pain. Proc. Natl. Acad. Sci. U S A, 1994, 91(25), 12013-12017.
12. Okamoto, T.; Hino, O. Expression of cyclooxygenase-1 and-2 mRNA in rat tissues: Tissue-specific difference in the expression of the basal level of mRNA. Int. J. Mol. Med., 2000, 6(4), 455-457.
13. Teismann, P.; Tieu, K.; Choi, D.; Wu, D.; Naini, A.; Hunot, S.; Vila, M.; Jackson-Lewis, V.; Przedborski, S. Cyclooxygenase-2 is instrumental in parkinson's disease neurodegeneration. Proc. Natl. Acad. Sci. U S A, 2003, 100(9), 5473-5478.
14. Edwards, J.; Mukherjee, R.; Munro, A.F.; Wells, A.C.; Almushatat, A.; Bartlett, J.M.S. HER2 and COX2 expression in human prostate cancer. Eur. J. Cancer, 2004, 40(1), 50-55.
15. Wang, D.; DuBois, R.N. The role of COX-2 in intestinal inflammation and colorectal cancer. Oncogene, 2010, 29(6), 781-788.
16. Hwang, D.; Scollard, D.; Byrne, J.; Levine, E. Expression of cyclooxygenase-1 and cyclooxygenase-2 in human breast cancer. J. Natl. Cancer Inst., 1998, 90(6), 455-460.
17. Jiménez, P.; García, A.; Santander, S.; Piazuelo, E. Prevention of cancer in the upper gastrointestinal tract with COX-inhibition, still an option? Curr. Pharm. Des., 2007, 13(22), 2261-2273.
18. Méric, J.; Rottey, S.; Olaussen, K.; Soria, J.; Khayat, D.; Rixe, O.; Spano, J.P. Cyclooxygenase-2 as a target for anticancer drug development. Crit. Rev. Oncol., 2006, 59(1), 51-64.
19. Greenhough, A.; Smartt, H.; Moore, A.; Roberts, H.; Williams, A.; Paraskeva, C.; Kaidi, A. The COX-2/PGE(2) pathway: Key roles in the hallmarks of cancer and adaptation to the tumour microenvironment. Carcinogenesis, 2009, 30(3), 377-386.
20. Ghosh, N.; Chaki, R.; Mandal, V.; Mandal, S. COX-2 as a target for cancer chemotherapy. Pharmacol. Rep., 2010, 62(2), 233-244.
21. Inoue, H.; Taba, Y.; Miwa, Y.; Yokota, C.; Miyagi, M.; Sasaguri, T. Transcriptional and posttranscriptional regulation of cyclooxygenase-2 expression by fluid shear stress in vascular endothelial cells. Arterioscler. Thromb. Vasc. Biol., 2002, 22(9), 1415-1420.
22. deVries, E.F.J. Imaging of cyclooxygenase-2 (COX-2) expression: Potential use in diagnosis and drug evaluation. Curr. Pharm. Des., 2006, 12(30), 3847-3856.
23. Prabhakaran, J.; Majo, V.; Simpson, N.; Van Heertum, R.; Mann, J.; Kumar, J. Synthesis of [C-11]celecoxib: A potential PET probe for imaging COX-2 expression. J. Labelled Comp. Radiopharm., 2005, 48(12), 887-895.
24. Takashima-Hirano, M.; Takashima, T.; Katayama, Y.; Wada, Y.; Sugiyama, Y.; Watanabe, Y.; Doi, H.; Suzuki, M. Efficient sequential synthesis of PET probes of the COX-2 inhibitor [11C]celecoxib and its major metabolite[11C]SC- 62807 and in vivo PET evaluation. Bioorg. Med. Chem., 2011, 19, 2997-3004.
25. Fujisaki, Y.; Kawamura, K.; Wang, W.; Ishiwata, K.; Yamamoto, F.; Kuwano, T.; Ono, M.; Maeda, M. Radiosynthesis and in vivo evaluation of 11C-labeled 1, 5-diarylpyrazole derivatives for mapping cyclooxygenases. Ann. Nucl. Med., 2005, 19(7), 617-625.
26. Gao, M.; Wang, M.; Miller, K.D.; Hutchins, G.D.; Zheng, Q. Synthesis of carbon-11 labeled celecoxib derivatives as new candidate PET radioligands for imaging of inflammation. Appl. Radiat. Isot., 2009, 67, 2019-2024.
27. Majo, V.; Prabhakaran, J.; Simpson, N.; Van Heertum, R.; Mann, J.; Kumar, J. A general method for the synthesis of aryl [C-11]methylsulfones: Potential PET probes for imaging cyclooxygenase-2 expression. Bioorg. Med. Chem. Lett., 2005, 15(19), 4268-4271.
28. de Vries, E.F.J.; Doorduin, J.; Dierckx, R.A.; van Waarde, A. Evaluation of [11C]rofecoxib as PET tracer for cyclooxygenase 2 overexpression in rat models of inflammation. Nucl. Med. Biol., 2008, 35, 35-42.
29. Wuest, F.; Kniess, T.; Bergmann, R.; Pietzsch, J. Synthesis and evaluation in vitro and in vivo of a 11C-labeled cyclooxygenase-2 (COX-2) inhibitor. Bioorg. Med. Chem., 2008, 16, 7662-7670.
30. Tanaka, M.; Fujisaki, Y.; Kawamura, K.; Ishiwata, K.; Qinggeletu, Y.F.; Mukai, T.; Maeda, M. Radiosynthesis and evaluation of 11Clabeled diaryl-substituted imidazole and indole derivatives for mapping cyclooxygenase-2. Biol. Pharm. Bull., 2006, 29(10), 2087-2094.
31. Prabhakaran, J.; Underwood, M.; Parsey, R.; Arango, V.; Majo, V.; Simpson, N.; van Heertum, R.; Mann, J.J.; Kumar, J.S. Synthesis and in vivo evaluation of [F-18]-4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl] benzene-sulfonamide as a PET imaging probe for COX-2 expression. Bioorg. Med. Chem., 2007, 15(4), 1802-1807.
32. Isakson,P.C.; Penning, T.D.; Talley, J.J.; Bertenshaw, S.R.; Carter, J.S.; Collins, P.W.; Docter, S.; Graneto, M.J.; Lee, L.F.; Malecha, J.W.; Miyashiro, J.M.; Rogers, R.S.; Rogier, D.J.; Yu, S.S.; AndersonG.D.; Burton E.G.; Cogburn J.N.; Gregory S.A.; Koboldt C.M.; Perkins, W.E.; Seibert, K.; Veenhuizen, A.W.; Zhang, Y.Y.; Isakson, P.C. Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl] benzenesulfonamide (SC-58635, celecoxib). J. Med. Chem., 1997, 40(9), 1347-1365.
33. Smith,C.J.; Zhang, Y.; Koboldt, C.M.; Muhammad, J.; Zweifel, B.S.; Shaffer, A.; Talley, J.J.; Masferrer, J.L.; Seibert, K.; Isakson, P.C. Pharmacological analysis of cyclooxygenase-1 in inflammation. Proc. Natl. Acad. Sci.U S A, 1998, 95(22), 13313-13318.
34. Kawamura, K.; Ishiwata, K. Improved synthesis of [C-11]SA4503, [C-11]MPDX and[C-11]TMSX by use of[C-11]methyl triflate. Ann. Nucl.Med., 2004, 18(2), 165-168.
35. Nagren, K.; Halldin, C. Methylation of amide and thiol functions with [C-11]methyl triflate, as exemplified by[C-11]NMSP, [C-11]flumazenil and[C-11]methionine. J. Labelled Comp. Radiopharm., 1998, 41(9), 831-841.
36. Gong, L.; Thorn, C.F.; Bertagnolli, M.M.; Grosser, T.; Altman, R.B.; Klein, T.E. Celecoxib pathways: pharmacokinetics and pharmacodynamics. Pharmacogenet. Genom., 2012, 22(4), 310-318.
37. Rodriguez, G.; Luis, A.; Cea-Soriano, L.; Tacconelli, S.; Patrignani, P. Coxibs: Pharmacology, Toxicity and Efficacy in Cancer Clinical Trials. Prospects for Chemoprevention of Colorectal Neoplasia, 2013, 67-93.
38. Szabó, G.; Fischer, J.; Kis-Varga, A.; Gyires, K. New celecoxib derivatives as anti-inflammatory agents. J. Med.Chem., 2008, 51(1), 142-147.
39. Ahuja, N.; Singh, A.; Singh, B. Rofecoxib: An update on physicochemical, pharmaceutical, pharmacodynamic and pharmacokinetic aspects. J. Pharm. Pharmacol., 2003, 55(7), 859-894.
40. Habeeb, A.G.; Rao, P.N.P.; Knaus, E.E. Design and syntheses of diarylisoxazoles: Novel inhibitors of cyclooxygenase-2 (COX-2) with analgesic-antiinflammatory activity. Drug. Dev. Res., 2000, 51(4), 273-286.
41. Dembo, G.; Park,S.B.; Kharasch, E.D. Central nervous system concentrations of cyclooxygenase-2 inhibitors in humans. Anesthesiology, 2005, 102(2), 409-415.
42. Lacroix, S.; Rivest, S. Effect of acute systemic inflammatory response and cytokines on the transcription of the genes encoding cyclooxygenase enzymes (COX-1 and COX-2) in the rat brain. J. Neurochem., 1998, 70(2), 452-466.
43. Quan, N.; Whiteside, M.; Herkenham, M. Cyclooxygenase-2 mRNA expression in rat brain after peripheral injection of lipopolysaccharide. Brain. Res., 1998, 802(1-2), 189-197.
44. Buursma, A.; de Vries, E.; Garssen, J.; Kegler, D.; van Waarde, A.; Schirm, J.; Hospers, G.; Mulder, N.; Vaalburg, W.; Klein, H. [F-18]FHPG positron emission tomography for detection of herpes simplex virus (HSV) in experimental HSV encephalitis. J.Virol., 2005, 79(12), 7721-7727.
45. Tzeng, S.; Hsiao, H.; Mak, O. Prostaglandins and cyclooxygenases in glial cells during brain inflammation. Curr. Drug Targets Inflamm. Allergy, 2005, 4(3), 335-340.
46. Yamada, S.; Kubota, K.; Kubota, R.; Ido, T.; Tamahashi, N. High accumulation of fluorine-18-fluorodeoxyglucose in turpentineinduced inflammatory tissue. J. Nuc. Med., 1995, 36(7), 1301-1306.
47. van Waarde, A.; Cobben, D.C.P.; Suurmeijer, A.J.H.; Maas, B.; Vaalburg, W.; de Vries, E,F,J.; Jager, P.L.; Hoekstra, H.J.; Elsinga, P.H. Selectivity of 18F-FLT and 18F-FDG for differentiating tumor from inflammation in a rodent model. J. Nuc. Med., 2004, 45(4), 695-700.
48. de Vries, E.F.J.; van Waarde, A.; Buursma, A.R.; Vaalburg, W. Synthesis and in vivo evaluation of 18F-desbromo-DuP-697 as a PET tracer for cyclooxygenase-2 expression. J. Nuc. Med., 2003, 44(10), 1700-1706.
49. Reitz,D.B.; Li, J.J.; Norton, M.B.; Reinhard, E.J.; Collins, J.T.; Anderson, G.D.; Gregory, S.A.; Koboldt, C.M.; Perkins, W.E. Selective cyclooxygenase inhibitors: Novel 1,2-diarylcyclopentenes are potent and orally active COX-2 inhibitors. J. Med.Chem., 1994, 37(23), 3878-3881.
50. Li,J.J.; Anderson, G.D.; Burton, E.G.; Cogburn, J.N.; Collins, J.T.; Garland, D.J.; Gregory, S.A.; Huang, H.; Isakson, P.C. 1,2-diarylcyclopentenes as selective cyclooxygenase-2 inhibitors and orally active anti-inflammatory agents. J. Med.Chem., 1995, 38(22), 4570-5478.
51. Barrio,J.R.; Satyamurthy, N.; Huang, S.C.; Keen, R.E.; Nissenson, C.H.; Hoffman, J.M.; Ackermann, R.F.; Bahn, M.M.; Mazziotta, J.C.; Phelps, M.E. 3-(2'-[18F]fluoroethyl)spiperone: In vivo biochemical and kinetic characterization in rodents, nonhuman primates, and humans. J. Cereb. Blood Flow Metab., 1989, 9(6), 830-839.
52. Almansa, C.; Alfón, J.; de Arriba,A.F.; Cavalcanti, F.L.; Escamilla, I.; Gómez, L.A.; Miralles, A.; Soliva, R.; Bartroli, J.; Carceller, E.; Merlos, M.; Garcia-Rafanell, J. Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5- diarylimidazoles. J. Med. Chem., 2003, 46(16), 3463-3475.
53. Hu, W.; Guo, Z.; Chu, F.; Bai, A.; Yi, X.; Cheng, G.; Li, J. Synthesis and biological evaluation of substituted 2-sulfonyl-phenyl-3-phenyl-indoles: A new series of selective COX-2 inhibitors. Bioorg. Med. Chem., 2003, 11(7), 1153-1160.
54. Weber, A.; Casini, A.; Heine, A.; Kuhn, D.; Supuran,C.T.; Scozzafava, A.; Klebe, G. Unexpected nanomolar inhibition of carbonic anhydrase by COX-2-selective celecoxib: New pharmacological opportunities due to related binding site recognition. J. Med. Chem., 2004, 47(3), 550-557.
55. McCarthy,T.J.; Sheriff, A.U.; Graneto, M.J.; Talley, J.J.; Welch, M.J. Radiosynthesis, in vitro validation, and in vivo evaluation of 18F-labeled COX-1 and COX-2 inhibitors. J. Nuc. Med., 2002, 43(1), 117-124.
56. Uddin, M.; Crews, B.; Ghebreselasie, K.; Huda, I.; Kingsley, P.; Ansari, M.; Tantawy, M.N.; Reese, J.; Marnett, L.J. Fluorinated COX-2 inhibitors as agents in PET imaging of inflammation and cancer. Can. Prev. Res., 2011, 4(10), 1536-1545.
57. Wüst,F.R.; Höhne, A.; Metz, P. Synthesis of 18F-labelled cyclooxygenase-2 (COX-2) inhibitors via stille reaction with 4-[18F]fluoroiodobenzene as radiotracers for positron emission tomography (PET). Org. Biomol. Chem., 2005, 3(3), 503-507.
58. Toyokuni, T.; Kumar,J.S.D.; Walsh, J.C.; Shapiro, A.; Talley, J.J.; Phelps, M.E.; Herschman, H.R.; Barrio, J.R; Satyamurthy, N. Synthesis of 4-(5-[18F]fluoromethyl-3-phenylisoxazol-4-yl)benzenesulfonamide, a new[18F]fluorinated analogue of valdecoxib, as a potential radiotracer for imaging cyclooxygenase-2 with positron emission tomography. Bioorg. Med. Chem. Lett., 2005, 15(21), 4699-4702.
59. Tian, H.; Lee, Z. Synthesis of 18F-labeled cyclooxygenase-2 (COX-2) inhibitor as a potential PET imaging agent. J. Labelled Compd. Radiopharmaceut., 2006, 49(7), 583-593.
60. Kniess, T.;Laube, M.;Bergmann, F.; Sehn, F.;Graf, F.; Steinbach, J.; Wuest, F.; Pietzsch, J. Radiosynthesis of a 18F-labeled 2,3-diarylsubstituted indole via McMurry coupling for functional characterization of cyclooxygenase-2 (COX-2) in vitro and in vivo. Bioorg. Med. Chem., 2012, 20, 3410-3421.
61. Alauddin, M.; Conti, P.; Mathew, T.; Fissekis, J.; Prakash, G.; Watanabe, K. Stereospecific fluorination of 1,3,5-tri-O-benzoylalpha-D-ribofuranose-2- sulfonate esters: Preparation of a versatile intermediate for synthesis of 2 '-[F-18]-fluoro-arabinonucleosides. J. Fluorine Chem., 2000, 106(1), 87-91.
62. Yasojima, K.; Schwab, C.; McGeer,E.G.; McGeer, P.L.. Distribution of cyclooxygenase-1 and cyclooxygenase-2 mRNAs and proteins in human brain and peripheral organs. Brain Res., 1999, 830(2), 226-236.
63. Ho, L.; Pieroni, C.; Winger, D.; Purohit,D.P.; Aisen, P.S.; Pasinetti, G.M. Regional distribution of cyclooxygenase-2 in the hippocampal formation in alzheimer's disease. J. Neurosci. Res., 1999, 57(3), 295-303.
64. Breder,C.D.; Dewitt, D.; Kraig, R.P. Characterization of inducible cyclooxygenase in rat brain. J. Comp. Neurol., 1995, 355(2), 296-315.
65. Talley, J.J. Substituted pyrazolyl benzenesulfonamides.U.S. Patent No. 5,466,823. 14 Nov. 1995.
66. Riese, J.; Hoff, T.; Nordhoff, A.; DeWitt,D.L.; Resch, K.; Kaever, V. Transient expression of prostaglandin endoperoxide synthase-2 during mouse macrophage activation. J. Leukoc. Biol., 1994, 55(4), 476-482.
67. Guha, M.; Mackman, N. LPS induction of gene expression in human monocytes. Cell Signal, 2001, 13(2), 85-94.
68. Wuest, F.; Kniess, T. Synthesis of 4-[F-18]fluoroiodobenzene and its application in sonogashira cross-coupling reactions. J. Labelled Compd. Radiopharmaceut., 2003, 46(8), 699-713.
69. Zhang, J.; Yuan, J.; Wang, Y.; Bible, R.; Breau, A. Pharmacokinetics and metabolism of a COX-2 inhibitor, valdecoxib, in mice. Drug Metab.Disposition., 2003, 31(4), 491-501.
70. Copeland, R.A.; Williams, J.M.; Giannaras, J.; Nurnberg, S.; Covington, M.; Pinto, D.; Pick, S.; Trzaskos, J.M. Mechanism of selective inhibition of the inducible isoform of prostaglandin G/H synthase. Proc. Natl. Acad. Sci.U S A, 1994, 91(23), 11202-11206.
71. Joshi, A.; Raghavan, N.; Williams, R.; Takahashi, K.; Shingu, H.; King, S. Simultaneous quantification of an antiinflammatory compound (DuP-697) and a potential metabolite (X6882) in human plasma and urine by high-performance liquid chromatography. J. Chromatogr., B: Anal. Technol. Biomed. Life Sci.,1994, 660(1), 143-150.
72. Beswick,P.J.; Blackaby, A.P.; Bountra, C.; Brown, T.; Browning, K.; Campbell, I.B.; Corfield, J.; Gleave, R.J.; Guntrip, S.B.; Hall, R.M.; Hindley, S.; Lambeth, R.F.; Lucas, F.; Mathews, N.; Naylor, A.; Player, H.; Price, H.S.; Sidebottom, P.J.; Taylor, N.L.; Webb, G.; Wiseman, J. Identification and optimisation of a novel series of pyrimidine based cyclooxygenase-2 (COX-2) inhibitors: utilisation of a biotransformation approach. Bioorg. Med. Chem. Lett., 2009, 19(15), 4509-4514.
73. Leblanc, Y.; Gauthier, J.; Ethier, D.; Guay, J.; Mancini, J.; Riendeau, D.; Tagari, P.; Vickers, P.; Wong, E.; Prasit, P.. Synthesis and biological evaluation of 2,3-diarylthiophenes as selective COX-2 and COX-1 inhibitors. Bioorg. Med. Chem. Lett., 1995, 5(18), 2123-2128.
74. Pinto,D.J.P.; Copeland, R.A.; Covington, M.B.; Pitts, W.J.; Batt, D.G.; Orwat, M.J.; Lam, G.N.; Joshi, A.; Chan, Y.; Wang, S.; Trzaskos, J.M.; Magolda, R.L.; Kornhauser, D.M. Chemistry and pharmacokinetics of diarylthiophenes and terphenyls as selective COX-2 inhibitors. Bioorg. Med. Chem. Lett., 1996, 6(24), 2907-3507.
75. Praveen Rao,P.N.; Amini, M.; Li, H.; Habeeb, A.G.; Knaus, E.E. Design, synthesis, and biological evaluation of 6-substituted-3-(4- methanesulfonylphenyl)-4-phenylpyran-2-ones: A novel class of diarylheterocyclic selective cyclooxygenase-2 inhibitors. J. Med. Chem., 2003, 46(23), 4872-4882.
76. Yang,D.J.; Bryant, J.; Chang, J.Y.; Mendez, R.; Oh, C.; Yu, D.; Ito, M.; Azhdarinia, A.; Kohanim, S.; Kim, E.E.; Lin, E.; Podoloff, D.A. Assessment of cyclooxygense-2 expression with 99m-Tclabeled celebrex. Anticancer Drugs, 2004, 15(3), 255-263.
77. Kabalka, G.; Mereddy, A.; Schuller, H. Synthesis of an iodine-123-labeled celecoxib analogue: A potential spect agent. J. Labelled Compd. Radiopharmaceut., 2005, 48(4), 295-300.
78. Kuge, Y.;Katada, Y.;Shimonaka, S.;Temma, T.;Kimura, H.;Kiyono, Y.; Yokota, C.; Minematusa, K.; Seki, K.; Tamaki, N.; Ohkura, K.; Saji, H. Synthesis and evaluation of radioiodinated cyclooxygenase-2 inhibitors as potential SPECT tracers for cyclooxygenase-2 expression. Nucl. Med. Biol., 2006, 33, 21-27.
79. Kuge, Y.;Obokata, N.;Kimura, H.;Katada, Y.; Temma, T.; Sugimoto, Y.; Aita, K.; Seki, K.; Tamaki, N.; Saji, H. Synthesis and evaluation of a radioiodinated lumiracoxib derivative for the imaging of cyclooxygenase-2 expression. Nucl. Med. Biol., 2009, 36, 869-876.
80. Verbruggen, A.M.; Nosco, D.L.; Van Nerom, C.G.; Bormans, G.M.; Adriaens, P.J.; De Roo, M.J. Technetium-99m-L,Lethylenedicysteine: A renal imaging agent, labeling and evaluation in animals. J. Nucl. Med., 1992, 33(4), 551-557.
81. Blondeau, P.; Berse, C.; Gravel, D. Dimerization of an intermediate during the sodium in liquid ammonia reduction of l-thiazolidine-4-carboxylic acid. Can. J. Chem., 1967, 45(1), 49-52.
82. Ilgan, S.; Yang,D.J.; Higuchi, T.; Zareneyrizi, F.; Bayhan, H.; Yu, D.; Kim, E.E.; Podoloff, D.A. 99mTc-ethylenedicysteine-folate: A new tumor imaging agent. synthesis, labeling and evaluation in animals. Can. Biother. Radiopharm., 1998, 13(6), 427-435.
83. Zareneyrizi, F.; Yang, D.; Oh, C.; Ilgan, S.; Yu, D.; Tansey, W.; Liu, C.; Kim, E.E.; Podoloff, D.A. Synthesis of [Tc-99m]ethylenedicysteine-colchicine for evaluation of antiangiogenic effect. Anticancer Drugs, 1999, 10(7), 685-692.
84. Yang, D.J.; Azhdarinia, A.; Wu, P.; Yu, D.F.; Tansey, W.; Kalimi, S.K.; Kim, E.E.; Podoloff, D.A. In vivo and in vitro measurement of apoptosis in breast cancer cells using 99mTc-EC-annexin V. Can. Biother Radiopharm., 2004, 16(1), 73-83.
85. Chang, H.C.; Weng, C.F. Cyclooxygenase-2 level and culture conditions influence NS398-induced apoptosis and caspase activation in lung cancer cells. Oncol. Rep., 2001, 8(6), 1321-1325.
86. Awara, W.M.; Alaa, E.E.; Magda, E.E.; Ahmed, E.G. The potential role of cyclooxygenase-2 inhibitors in the treatment of experimentally-induced mammary tumour: Does celecoxib enhance the antitumour activity of doxorubicin? Pharmacol. Res., 2004, 50, 487-498.
87. Schuller, H.; Kabalka, G.; Smith, G.; Mereddy, A.; Akula, M.; Cekanova, M. Detection of overexpressed COX-2 in precancerous lesions of hamster pancreas and lungs by molecular imaging: Implications for early diagnosis and prevention. ChemMedChem, 2006, 1(6), 603-610.
88. Schuller, H.M. Mechanisms of smoking-related lung and pancreatic adenocarcinoma development. Nat. Rev. Can., 2002, 2(6), 455-463.
89. Schuller, H.; Zhang, L.; Weddle, D.; Castonguay, A.; Walker, K.; Miller, M. The cyclooxygenase inhibitor ibuprofen and the FLAP inhibitor MK886 inhibit pancreatic carcinogenesis induced in hamsters by transplacental exposure to ethanol and the tobacco carcinogen NNK. J. Cancer Res. Clin. Oncol., 2002, 128(10), 525-532.
90. Schuller, H.; Cekanova, M. NNK-induced hamster lung adenocarcinomas over-express 2-adrenergic and EGFR signaling pathways. Lung Cancer, 2005, 49, 35-45.
91. Esser, R.; Berry, C.; Du, Z.; Dawson, J.; Fox, A.; Fujimoto, R.A.; Heston, W.; Kimble, E.F.; Koehler, J.; Peppard, J.; Quadros, E.; Quintavalla, J.; Toscano, K.; Urban, L.; van Duzer, J.; Zhang, X.; Zhou, S.; Marshall, P.J. Preclinical pharmacology of lumiracoxib: A novel selective inhibitor of cyclooxygenase-2. Br. J.Pharmacol., 2005, 144(4), 538-550.
92. Buvanendran, A.; Barkin, R. Lumiracoxib. Drugs Today (Barc)., 2007, 43(3), 137-147.
93. Bannwarth, B.; Berenbaum, F. Clinical pharmacology of lumiracoxib, a second-generation cyclooxygenase 2 selective inhibitor. Expert Opin. Investig. Drugs., 2005, 14(4), 521-533.
94. Medzhitov, R. Origin and physiological roles of inflammation. Nature, 2008, 454, 428-435.
95. Debucquoy, A.; Devos, E.; Vermaelen, P.; Landuyt, W.; De Weer, S.; Van Den Heuvel, F.; Haustermans, K. 18F-FLT and 18F-FDG PET to measure response to radiotherapy combined with celecoxib in two colorectal xenograft models. Int. J. Radiat. Biol.,2009, 85(9), 763-771.