Radiosynthesis and evaluation of11C-Labeled diaryl-substituted imidazole and indole derivatives for mapping cyclooxygenase-2

Biological and Pharmaceutical Bulletin

Volumn 29, Issue 10, 2006, Pages 2087-2094

  Tanaka, Mariko ^a   Fujisaki, Yoshihiko ^a   Kawamura, Kazunori ^b   Ishiwata, Kiichi ^b   Qinggeletu, ^b   Yamamoto, Fumihiko ^a   Mukai, Takahiro ^a   Maeda, Minoru ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b TOKYO METROPOLITAN INSTITUTE OF GERONTOLOGY   (Japan)

Author keywords

Carbon 11; Cyclooxygenase 2 inhibitor; P glycoprotein; Radiosynthesis; Tissue distribution

Indexed keywords

2 (4 AMINOSULFONYLPHENYL) 3 (4 METHOXYPHENYL)INDOLE C 11; 4 [4 CHLORO 5 (3 FLUORO 4 METHOXYPHENYL)IMIDAZOL 1 YL]BENZENESULFONAMIDE C 11; 4 CHLORO 5 (3 FLUORO 4 METHOXYPHENYL) 1 (4 METHYLSULFONYLPHENYL)IMIDAZOLE C 11; ACETONE; CARBON 11; CELECOXIB; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; CYCLOSPORIN A; GLYCOPROTEIN P; GLYCOPROTEIN P INHIBITOR; IMIDAZOLE DERIVATIVE; INDOLE DERIVATIVE; ISOPROTEIN; RADIOPHARMACEUTICAL AGENT; SODIUM HYDROXIDE; UNCLASSIFIED DRUG; CARBON; DIAGNOSTIC AGENT;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; AUTORADIOGRAPHY; BODY REGIONS; CONTROLLED STUDY; DOSE RESPONSE; DRUG ACTIVITY; DRUG DISTRIBUTION; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; EX VIVO STUDY; IN VIVO STUDY; ISOTOPE LABELING; LIVER CELL CARCINOMA; MALE; METHYLATION; NONHUMAN; PEPTIDE MAPPING; POSITRON EMISSION TOMOGRAPHY; RADIOCHEMISTRY; RAT; TISSUE DISTRIBUTION; ANIMAL; METABOLISM; PHYSIOLOGY;

ANIMALS; AUTORADIOGRAPHY; CARBON RADIOISOTOPES; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; IMIDAZOLES; INDOLES; ISOTOPE LABELING; MALE; P-GLYCOPROTEIN; RADIOPHARMACEUTICALS; RATS; TISSUE DISTRIBUTION;

EID: 33749427395     PISSN: 09186158     EISSN: 13475215     Source Type: Journal    
DOI: 10.1248/bpb.29.2087     Document Type: Article

References (39)

1. Simmons D. L., Botting R. M., Hla T., Pharmacol. Rev., 56, 387-437 (2004).
2. O'Banion M. K., Sadowski H. B., Winn V., Young D. A., J. Biol. Chem., 266, 23261-23267 (1991).
3. Kujubu D. A., Fletcher B. S., Varnum B. C., Lim R. W., Herschman H. R., J. Biol. Chem., 266, 12866-12872 (1991).
4. Vane J. R., Bakhe Y. S., Botting R. M., Ann. Rev. Pharmacol. Toxicol., 38, 97-120 (1998).
5. Futaki N., Takahashi S., Yokoyama M., Arai I., Higuchi S., Otomo S., Prostaglandins, 47, 55-59 (1994).
6. Hersh E. V., Lally E. T., Moore P. A., Curr. Med. Res. Opin., 21, 1217-1226 (2005).
7. Howe L. R., Subbaramaiah K., Brown A. M., Dannenberg A. J., Endocr. Relat. Cancer., 8, 97-114 (2001).
8. Fournier D. B., Gordon G. B., J. Cell Biochem., 34 (Suppl.), 97-102 (2000).
9. Ermert L., Dierkes C., Ermert M., Clin. Cancer Res., 9, 1604-1610 (2003).
10. Tong W., Biochim. Biophys. Acta, 1755, 135-150 (2005).
11. Marks F., Muller-Decker K., Furstenberger G., Toxicology, 153, 11-26 (2000).
12. Kaufmann W. E., Andreasson K. I., Isakson P. C., Worley P. F., Prostaglandins, 54, 601-624 (1997).
13. Minghetti L., J. Neuropathol. Exp. Neurol., 63, 901-910 (2004).
14. Kam P. C. A., See A. U. L., Anaesthesia, 55, 442-449 (2000).
15. Harvey R. H., John J. T., Raymond D., Mol. Imag. Biol., 5, 286-303 (2003).
16. 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., Anderson G. 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., J. Med. Chem., 40, 1347-1365 (1997).
17. Prasit P., Wang Z., Brideau C., Chan C. C., Charleson S., Cromlish W., Ethier D., Evans J. F., Ford-Hutchinson A. W., Gauthier J. Y., Gordon R., Guay J., Gresser M., Kargman S., Kennedy B., Leblanc Y., Leger S., Mancini J., O'Neill G. P., Ouellet M., Percival M. D., Perrier H., Riendeau D., Rodger I., Tagari P., Therien M., Vickers P., Wong E., Xu L. J., Young R. N., Zamboni R., Biooorg. Med. Chem. Lett., 9, 1773-1778 (1999).
18. McCarthy T. J., Sheriff A. U., Graneto M. J., Talley J. J., Welch M. J., J. Nucl. Med., 43, 117-124 (2002).
19. de Vries E. F., van Waarde A., Buursma A. R., Vaalburg W., J. Nucl. Med., 44,1700-1706 (2003).
20. Prabhakaran J., Majo V. J., Simpson N. R., van Heertum R. L., Mann J. J., Kumar J. S., J. Label. Compd. Radiopharm., 48, 887-895 (2005).
21. Toyokuni T., Kumar J. S., Walsh J. C., Shapiro A., Talley J. J., Phelps M. E., Herschman H. R., Barrio J. R., Satyamurthy N., Bioorg. Med. Chem. Lett., 15, 4699-4702 (2005).
22. Wust F. R., Hohne A., Metz P., Org. Biomol. Chem., 3, 503-507 (2005).
23. Fujisaki Y., Kawamura K., Wang W. F., Ishiwata K., Yamamoto F., Kuwano T., Ono M., Maeda M., Ann. Nucl. Med., 19, 617-625 (2005).
24. Carmen A., José A., Alberto F. A., Fernando L. C., Ignasi E., Luis A. G., Agusti M., Robert S., Javier B., Elena C., Manuel M., Julian G. R., J. Med. Chem., 46, 3463-3475 (2003).
25. Hu W., Guo Z., Chu F., Bai A., Yi X., Cheng G., Li J., Bioorg. Med. Chem., 11, 1153-1160 (2003).
26. Kubota K., Ishiwata K., Kubota R., Yamada S., Takahashi J., Abe Y., Fukuda H., Ido T., J. Nucl. Med., 37, 320-325 (1996).
27. Ishiwata K., Seki H., Ishii K., Ishii S., Nozaki T., Senda M., Appl. Radiat. Isot., 45, 439-443 (1994).
28. Ueda K., Okamura N., Hirai M., Tanigawara Y., Saeki T., Kioka N., Komano T., Hori R., J. Biol. Chem., 267, 24248-24252 (1992).
29. Tanigawara Y., Okamura N., Hirai M., Yasuhara M., Ueda K., Kioka N., Komano T., Hori R., J. Pharmacol. Exp. Ther., 263, 840-845 (1992).
30. Marnett L. J., Kalgutkar A. S., Curr. Opin. Chem. Biol., 2, 482-490 (1998).
31. de Vries E. F., Kortekaas R., van Waarde A., Dijkstra D., Elsinga P. H., Vaalburg W., J. Nucl. Med., 46, 1384-1392 (2005).
32. Hendrikse N. H., de Vries E. G., Eriks-Fluks L., van der Graaf W. T., Hospers G. A., Willemsen A. T., Vaalburg W., Franssen E. J., Cancer Res., 59, 2411-2416 (1999).
33. Breder C. D., Dewitt D., Kraig R. P., J. Comp. Neurol., 355, 296-315 (1995).
34. Yamagata K., Andreasson K. I., Kaufmann W. E., Barnes C. A., Worley P. F., Neuron, 11, 371-386 (1993).
35. de Lange E. C., Adv. Drug Deliv. Rev., 56, 1793-1809 (2004).
36. Pastorekova S., Parkkila S., Pastorek J., Supuran C. T., J. Enzyme Inhibi. Med. Chem., 19, 199-229 (2004).
37. Weber A., Casini A., Heine A., Kuhn D., Supuran C. T., Scozzafava A., Klebe G., J. Med. Chem., 47, 550-557 (2004).
38. Spencer A. G., Woods J. W., Arakawa T., Singer I. I., Smith W. L., J. Biol. Chem., 273, 9886-9893 (1998).
39. Parfenova H., Parfenov V. N., Shlopov B. V., Levine V., Falkos S., Pourcyrous M., Leffler C. W., Am. J. Physiol. Cell. Physiol., 281, C166-C167 (2001).