Nuclear Medicine and Biology
Volume 33, Issue 1 , Pages 21-27 , January 2006

Synthesis and evaluation of radioiodinated cyclooxygenase-2 inhibitors as potential SPECT tracers for cyclooxygenase-2 expression

  • Yuji Kuge

      Affiliations

    • Department of Patho-Functional Bioanalysis, Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501, Japan
    • Corresponding Author InformationCorresponding author. Tel.: +81 75 753 4608; fax: +81 75 753 4568.
  • ,
  • Yumiko Katada

      Affiliations

    • Department of Patho-Functional Bioanalysis, Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501, Japan
  • ,
  • Sayaka Shimonaka

      Affiliations

    • Department of Patho-Functional Bioanalysis, Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501, Japan
  • ,
  • Takashi Temma

      Affiliations

    • Department of Patho-Functional Bioanalysis, Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501, Japan
  • ,
  • Hiroyuki Kimura

      Affiliations

    • Department of Patho-Functional Bioanalysis, Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501, Japan
  • ,
  • Yasushi Kiyono

      Affiliations

    • Radioisotopes Research Laboratory, Kyoto University Hospital, Faculty of Medicine, Kyoto University, Kyoto 606-8507, Japan
  • ,
  • Chiaki Yokota

      Affiliations

    • Cerebrovascular Laboratory, National Cardiovascular Center Research Institute, Osaka 565-8565, Japan
  • ,
  • Kazuo Minematsu

      Affiliations

    • Cerebrovascular Division, Department of Medicine, National Cardiovascular Center Research Institute, Osaka 565-8565, Japan
  • ,
  • Koh-ichi Seki

      Affiliations

    • Central Institute of Isotope Science, Hokkaido University, Hokkaido 060-8638, Japan
  • ,
  • Nagara Tamaki

      Affiliations

    • Department of Nuclear Medicine, Graduate School of Medicine, Hokkaido University, Hokkaido 060-8638, Japan
  • ,
  • Kazue Ohkura

      Affiliations

    • Department of Radiopharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Hokkaido 061-0293, Japan
  • ,
  • Hideo Saji

      Affiliations

    • Department of Patho-Functional Bioanalysis, Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501, Japan

Received 26 August 2005 ,Revised 30 September 2005 ,Accepted 5 October 2005.

References 

  1. Davies NM, Good RL, Roupe KA, Yanez JA. Cyclooxygenase-3: axiom, dogma, anomaly, enigma or splice error? — Not as easy as 1, 2, 3. J Pharm Pharm Sci. 2004;7:217–226
  2. FitzGerald GA. COX-2 and beyond: approaches to prostaglandin inhibition in human disease. Nat Rev Drug Discov. 2003;2:879–890
  3. Collaco-Moraes Y, Aspey B, Harrison M, de-Belleroche J. Cyclo-oxygenase-2 messenger RNA induction in focal cerebral ischemia. J Cereb Blood Flow Metab. 1996;16:1366–1372
  4. Nogawa S, Zhang F, Ross ME, Iadecola C. Cyclo-oxygenase-2 gene expression in neurons contributes to ischemic brain damage. J Neurosci. 1997;17:2746–2755
  5. Hara K, Kong DL, Sharp FR, Weinstein PR. Effect of selective inhibition of cyclooxygenase 2 on temporary focal cerebral ischemia in rats. Neurosci Lett. 1998;256:53–56
  6. Yokota C, Inoue H, Kuge Y, Abumiya T, Tagaya M, Hasegawa Y, et al. Cyclooxygenase-2 expression associated with spreading depression in a primate model. J Cereb Blood Flow Metab. 2003;23:395–398
  7. Yokota C, Kuge Y, Inoue H, Tagaya M, Kito G, Susumu T, et al. Post-ischemic cyclooxygenase-2 expression is regulated by the extent of cerebral blood flow reduction in non-human primates. Neurosci Lett. 2003;341:37–40
  8. Yokota C, Kaji T, Kuge Y, Inoue H, Tamaki N, Minematsu K. Temporal and topographic profiles of cyclooxygenase-2 expression during 24 h of focal brain ischemia in rats. Neurosci Lett. 2004;357:219–222
  9. Yokota C, Kuge Y, Inoue H, Tamaki N, Minematsu K. Bilateral induction of the S-100A9 gene in response to spreading depression is modulated by the cyclooxygenase-2 activity. J Neurol Sci. 2005;234:11–16
  10. Kaji T, Kuge Y, Yokota C, Tagaya M, Inoue H, Shiga T, et al. Characterisation of [123I]iomazenil distribution in a rat model of focal cerebral ischaemia in relation to histopathological findings. Eur J Nucl Med Mol Imaging. 2004;31:64–70
  11. Herschman HR, Talley JJ, DuBois R. Cyclooxygenase 2 (COX-2) as a target for therapy and noninvasive imaging. Mol Imaging Biol. 2003;5:286–303
  12. McCarthy TJ, Sheriff AU, Graneto MJ, Talley JJ, Welch MJ. Radiosynthesis, in vitro validation, and in vivo evaluation of 18F-labeled COX-1 and COX-2 inhibitors. J Nucl Med. 2002;43:117–124
  13. de Vries EF, van Waarde A, Buursma AR, Vaalburg W. Synthesis and in vivo evaluation of 18F-desbromo-DuP-697 as a PET tracer for cyclooxygenase-2 expression. J Nucl Med. 2003;44:1700–1706
  14. Wust FR, Hohne 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;3:503–507
  15. Yang DJ, Bryant J, Chang JY, Mendez R, Oh CS, Yu DF, et al. Assessment of cyclooxygense-2 expression with 99mTc-labeled celebrex. Anticancer Drugs. 2004;15:255–263
  16. Kabalka GW, Mereddy AR, Schuller HM. Synthesis of an iodine-123-labeled celecoxib analogue: a potential SPECT agent. J Label Compd Radiopharm. 2005;48:295–300
  17. Boddy A, Edwards P, Rowland M. Binding of sulfonamides to carbonic anhydrase: influence on distribution within blood and on pharmacokinetics. Pharm Res. 1989;6:203–209
  18. Weber A, Casini A, Heine A, Kuhn D, Supuran CT, Scozzafava A, et al. Unexpected nanomolar inhibition of carbonic anhydrase by COX-2-selective celecoxib: new pharmacological opportunities due to related binding site recognition. J Med Chem. 2004;47:550–557
  19. Kiyono Y, Kanegawa N, Kawashima H, Kitamura Y, Iida Y, Saji H. Evaluation of radioiodinated (R)-N-methyl-3-(2-iodophenoxy)-3-phenylpropanamine as a ligand for brain norepinephrine transporter imaging. Nucl Med Biol. 2004;31:147–153
  20. Kam PC, See AU. Cyclo-oxygenase isoenzymes: physiological and pharmacological role. Anaesthesia. 2000;55:442–449
  21. Warner TD, Giuliano F, Vojnovic I, Bukasa A, Mitchell JA, Vane JR. Nonsteroid drug selectivities for cyclo-oxygenase-1 rather than cyclo-oxygenase-2 are associated with human gastrointestinal toxicity: a full in vitro analysis. Proc Natl Acad Sci U S A. 1999;96:7563–7568
  22. Kato M, Nishida S, Kitasato H, Sakata N, Kawai S. Cyclooxygenase-1 and cyclooxygenase-2 selectivity of non-steroidal anti-inflammatory drugs: investigation using human peripheral monocytes. J Pharm Pharmacol. 2001;53:1679–1685

PII: S0969-8051(05)00265-9

doi: 10.1016/j.nucmedbio.2005.10.004

Nuclear Medicine and Biology
Volume 33, Issue 1 , Pages 21-27 , January 2006