Nuclear Medicine and Biology
Volume 34, Issue 3 , Pages 273-281 , April 2007

Synthesis and biodistribution of 3′-fluoro-5-[131I]iodo-2′-deoxyuridine: a comparative study of [131I]FLIdU and [18F]FLT

Received 13 April 2006 ,Revised 20 November 2006 ,Accepted 25 December 2006.

References 

  1. Shields AF. PET imaging with 18F-FLT and thymidine analogs: promise and pitfalls. J Nucl Med. 2003;44:1432–1434
  2. Sherley JL, Kelly TJ. Regulation of human thymidine kinase during the cell cycle. J Biol Chem. 1988;263:8350–8358
  3. Commerford SL. Biological stability of 5-iodo-2′-deoxyuridine labeled with iodine-125 after its incorporation into the deoxyribonucleic acid of the mouse. Nature. 1965;4987:949–950
  4. Eary JF, Mankoff DA, Spence AM, et al. 2-[C-11]Thymidine imaging of malignant brain tumors. Cancer Res. 1999;59:615
  5. Seitz U, Wagner M, Vogg AT, et al. In vivo evaluation of 5-[18F]fluoro-2′-deoxyuridine as tracer for positron emission tomography in a murine pancreatic cancer model. Cancer Res. 2001;61:3853–3857
  6. Buchegger F, Vieira J-M, Blaeuenstein P, et al. Preclinical Auger and gamma radiation dosimetry for fluorodeoxyuridine-enhanced tumour proliferation scintigraphy with [123I]iododeoxyuridine. Eur J Nucl Med. 2003;30:239–246
  7. Lu L, Samuelson L, Bergström M, et al. Rat studies comparing 11C-FMAU, 18F-FLT, and 76Br-BFU as proliferation markers. J Nucl Med. 2002;43:1688–1698
  8. Toyohara J, Fujibayashi Y. Trends in nucleoside tracers for PET imaging of cell proliferation. Nucl Med Biol. 2003;30:681–685
  9. Shields AF, Grierson JR, Dohmen BM, et al. Imaging proliferation in vivo with [F-18]FLT and positron emission tomography. Nat Med. 1998;4:1334
  10. Fukushima M, Suzuki N, Emura T, et al. Structure and activity of specific inhibitors of thymidine phosphorylase to potentiate the function of antitumor 2′-deoxyribonucleosides. Biochem Pharmacol. 2000;59:1227–1236
  11. Focher F, Spadari S. Thymidine phosphorylase: a two-face janus in anticancer chemotherapy. Curr Cancer Drug Targets. 2001;1:141–153
  12. Coderre JA, Santi DV, Matsuda A, et al. Mechanism of action of 2′,5-difluoro-1-arabinosyluracil. J Med Chem. 1983;26:1149–1152
  13. Shields AF, Grierson JR, Kozawa SM, et al. Development of labeled thymidine analogs for imaging tumor proliferation. Nucl Med Biol. 1996;23:17–22
  14. Wagner M, Seitz U, Buck A, et al. 3′-[18F]Fluoro-3′-deoxythymidine ([18F]-FLT) as positron emission tomography tracer for imaging proliferation in a murine B-cell lymphoma model and in the human disease. Cancer Res. 2003;63:2681–2687
  15. Grierson JR, Schwartz JL, Muzi M, et al. Metabolism of 3′-deoxy-[F-18]fluorothymidine in proliferating A549 cells: validations for positron emission tomography. Nucl Med Biol. 2004;31:829–837
  16. Munch-Petersen B, Cloos L, Tyrsted G, et al. Diverging substrate specificity of pure human thymidine kinase 1 and 2 against antiviral dideoxynucleosides. J Biol Chem. 1991;266:9032–9038
  17. Langen P, Kowollik G, Etzold G, et al. The phosphorylation of 3′-deoxy-3′-fluorothymidine and its incorporation into DNA in a cell-free system. Acta Biol Med Ger. 1972;29:483–494
  18. Seitz U, Wagner M, Neumaier B, et al. Evaluation of pyrimidine metabolising enzymes and in vitro uptake of 3′-[18F]fluoro-3′-deoxythymidine ([18F]FLT) in pancreatic cancer cell lines. Eur J Nucl Med. 2002;29:1174–1181
  19. Morse G, Shelton M, O'Donnell A. Comparative pharmacokinetics of antiviral nucleoside analogues. Clin Pharmacokinet. 1993;24:101–123
  20. Shields AF, Briston DA, Chandupatla S, et al. A simplified analysis of [18F]3′-deoxy-3′-fluorothymidine metabolism and retention. Eur J Nucl Med Mol Imaging. 2005;32:1269–1275
  21. Veal GJ, Back DJ. Metabolism of zidovudine. Gen Pharmacol. 1995;26:1469–1475
  22. Vose JM, Wahl RL, Saleh M, et al. Multicenter phase II study of iodine-131 tositumomab for chemotherapy-relapsed/refractory low-grade and transformed low-grade B-cell non-Hodgkin's lymphomas. J Clin Oncol. 2000;18:1316–1323
  23. Jazirehi AR, Bonavida B. Cellular and molecular signal transduction pathways modulated by rituximab (rituxan, anti-CD20 mAb) in non-Hodgkin's lymphoma: implications in chemosensitization and therapeutic intervention. Oncogene. 2005;24:2121–2143
  24. Gati WP, Misra HK, Knaus EE, et al. Structural modifications at the 2′- and 3′-positions of some pyrimidine nucleosides as determinants of their interaction with the mouse erythrocyte nucleoside transporter. Biochem Pharmacol. 1984;33:3325–3331
  25. Gati WP, Kugyelka JG, Knaus EE, et al. Pyrimidine nucleosides modified at the 2′- and 3′-positions: investigation of their interaction with rat liver pyrimidine nucleoside kinases. In:  Billinghurst MW editors. Current applications in radiopharmacology. Toronto: Pergamon Press; 1986;p. 317–322
  26. Balzarini J, Van Aerschot A, Pauwels R, et al. 5-Halogeno-3′-fluoro-2′,3′-dideoxyuridines as inhibitors of human immunodeficiency virus (HIV): potent and selective anti-HIV activity of 3′-fluoro-2′,3′-dideoxy-5-chlorouridine. Mol Pharmacol. 1989;35:571–577
  27. Machulla H-J, Blocher A, Kuntzsch M, et al. Simplified labeling approach for synthesizing 3′-deoxy-3′-[18F]fluorothymidine ([18F]FLT). J Radioanal Nucl Chem. 2000;243:843–846
  28. Becouarn S, Czernecki S, Valéry J-M. Efficient transformation of thymidine into 2′,3′-didehydro-2′,3′-dideoxy-thymidine (D4T) involving opening of a 2,3′-anhydro derivative by phenylselenol. Nucleosides Nucleotides. 1995;14:1227–1232
  29. Kluin-Nelemans HC, Limpens J, Meerabux J, et al. A new non-Hodgkin's B-cell line (DoHH2) with a chromosomal translocation t(14;18)(q32;q21). Leukemia. 1991;5:221–224
  30. Chu SYF, Ekström LP, Firestone RB. WWW table of radioactive isotopes. LBNL/Department of Physics, Lund University. Berkeley, USA/Sweden. URL: http://nucleardata.nuclear.lu.se/nucleardata/toi/databaseversion2/28/1999
  31. Mier W, Haberkorn U, Eisenhut M. [18F]FLT; portrait of a proliferation marker. Eur J Nucl Med. 2002;29:165
  32. Zuckier LS, Dohan O, Li Y, et al. Kinetics of perrhenate uptake and comparative biodistribution of perrhenate, pertechnetate, and iodide by NaI symporter-expressing tissues in vivo. J Nucl Med. 2004;45:500–507
  33. Vogg ATJ, Neumaier B, Schmid M, et al. Kinetic investigations of the electrophilic nca radioiodination of 2′-deoxyuridine. J Label Compd Radiopharm. 2001;44:S970–S972
  34. Garrett C, Wataya Y, Santi DV. Thymidylate synthetase. Catalysis of dehalogenation of 5-bromo- and 5-iodo-2′-deoxyuridylate. Biochemistry. 1979;18:2798–2804
  35. Carreras CW, Santi DV. The catalytic mechanism and structure of thymidylate synthase. Ann Rev Biochem. 1995;64:721–762
  36. Wataya Y, Negishi K, Hayatsu H. Debromination of 5-bromo-2′-deoxyuridine by cysteine. Formation of deoxyuridine and S-[5-(2′-deoxyuridyl)]cysteine. Biochemistry. 1973;12:3992–3998
  37. Lawrence TS, Davis MA, McKeever PE, et al. Fluorodeoxyuridine-mediated modulation of iododeoxyuridine incorporation and radiosensitization in human colon cancer cells in vitro and in vivo. Cancer Res. 1991;51:3900–3905
  38. Stetson PL, Normolle DP, Knol JA, et al. Biochemical modulation of 5-bromo-2′-deoxyuridine and 5-iodo-2′-deoxyuridine incorporation into DNA in VX2 tumor-bearing rabbits. J Natl Cancer Inst. 1991;83:1659–1667
  39. Mester J, DeGoeij K, Sluyser M. Modulation of [5-125I]iododeoxyuridine incorporation into tumor and normal tissue DNA by methotrexate and thymidylate synthase inhibitors. Eur J Cancer. 1996;32A:1603–1608
  40. Kriss JP, Maruyama Y, Tung LA, et al. The fate of 5-bromodeoxyuridine, 5-bromodeoxycytidine and 5-iododeoxycytidine in man. Cancer Res. 1963;23:260–268
  41. Mercer JR, Xu L-H, Knaus EE, et al. Synthesis and tumor uptake of 5-82Br- and 5-131I-labeled 5-halo-1-(2-fluoro-2-deoxy-β-d-ribofuranosyl)uracils. J Med Chem. 1989;32:1289–1294
  42. Borbath I, Grégoire V, Bergström M, et al. Use of 5-[76Br]bromo-2′-fluoro-2′-deoxyuridine as a ligand for tumour proliferation: validation in an animal tumour model. Eur J Nucl Med. 2001;29:19–27
  43. Kao C-HK, Waki A, Sassaman MB, et al. Evaluation of [76Br]FBAU 3′,5′-dibenzoate as lipophilic prodrug for brain imaging. Nucl Med Biol. 2002;29:527–535
  44. Landowski CP, Lorenzi PL, Song X, et al. Nucleoside ester prodrug substrate specificity of liver carboxylesterase. J Pharmacol Exp Ther. 2006;316:572–580

PII: S0969-8051(07)00009-1

doi: 10.1016/j.nucmedbio.2006.12.010

Nuclear Medicine and Biology
Volume 34, Issue 3 , Pages 273-281 , April 2007

Article Tools

* Image Usage & Resolution