Preparation of 5-[131(I)]Iodo- and 5-[211at]astato-1(2-deoxy-2- fluoro-β-d-arabinofuranosyl)uracil by a halodestannylation reaction

Nuclear Medicine and Biology

Volumn 25, Issue 5, 1998, Pages 487-496

  Vaidyanathan, Ganesan ^a   Zalutsky, Michael R ^a  

^a DUKE UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 DEOXY 2 FLUORO BETA DEXTRO ARABINOFURANOSYL) 5 ASTATOURACIL AT 211; 2' DEOXY 5 ASTATOURIDINE; 5 TRIMETHYLSTANNYL 1 (2 DEOXY 2 FLUORO BETA DEXTRO ARABINOFURANOSYL)URACIL; ASTATINE 211; FILAURIDINE I 131; IDOXURIDINE; IODINE 131; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG; 5 (211 AT)ASTATO 1 (2 DEOXY 2 FLUORO ARABINOFURANOSYL)URACIL; 5-(211-AT)ASTATO-1-(2-DEOXY-2-FLUORO-ARABINOFURANOSYL)URACIL; DNA; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FIALURIDINE; RADIOACTIVE IODINE; TIN; URACIL ARABINOSIDE;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BLOOD; CHEMICAL REACTION; DEIODINATION; DRUG ACCUMULATION; DRUG DISTRIBUTION; DRUG STABILITY; DRUG SYNTHESIS; DRUG UPTAKE; GLIOMA CELL; HUMAN; MOUSE; NONHUMAN; THYROID GLAND; ANIMAL; CELL CULTURE; CELL LINE; CHEMISTRY; ISOTOPE LABELING; METABOLISM; SYNTHESIS; TISSUE DISTRIBUTION;

ANIMALS; ARABINOFURANOSYLURACIL; CELL LINE; DNA; DRUG STABILITY; HUMANS; INDICATORS AND REAGENTS; IODINE RADIOISOTOPES; ISOTOPE LABELING; MICE; RADIOPHARMACEUTICALS; TIN; TISSUE DISTRIBUTION; TUMOR CELLS, CULTURED;

EID: 0032105474     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0969-8051(98)00004-3     Document Type: Article

References (37)

1. Ahluwalia G. S., Driscoll J. S., Ford H. Jr, Johns D. G. Comparison of the DNA incorporation in human MOLT-4 cells of two 2′-β-fluoronucleosides, 2′-β-2′-3′-dideoxyadenosine and fialuridine. J. Pharm. Sci. 85:1996;454-455.
2. Aoyama H. Stereoselective synthesis of anomers of 5-substituted 2′-deoxyuridines. Bull. Chem. Soc. Japan. 60:1987;2073-2077.
3. Azure M. T., Archer R. D., Sastry K. S. R., Rao D. V., Howell R. W. Biological effect of lead-212 localized in the nucleus of mammalian cells Role of recoil energy in the radiotoxicity of internal alpha-particle emitters . Radiat. Res. 140:1994;276-283.
4. Barton G. J., Ponting C. P., Spraggon G., Finnis C., Sleep D. Human platelet-derived endothelial cell growth factor is homologous to Escherichia coli thymidine phosphorylase. Protein Sci. 1:1992;688-690.
5. Bigner S. H., Friedman H. S., Biegel J. A., Wikstrand C. J., Mark J., Gebhardt R., et al. Specific chromosomal abnormalities characterize four established cell lines derived from malignant human gliomas. Acta Neuropathol. 72:1986;86-97.
6. 11C]-FMAU) A potential nucleoside analog for in vivo study of cellular proliferation with PET . Nucl. Med. Biol. 22:1995;783-789.
7. 125I-labeled 5-iodo-2′-deoxyuridine into the DNA of mouse mammary tumors. Fry P.J.M. Normal and Malignant Cell Growth. 1969;186-201 Springer-Verlag, New York.
8. Furukawa T., Yoshimura A., Sumizawa T., Haraguchi M., Akiyama S., Fukui K., et al. Angiogenic factor. Nature. 356:1992;668.
9. 2 fragment. Cancer Res. 50:1990;3514-3520.
10. Grant A. J., Feinberg A., Chou T.-C., Watanabe K. A., Fox J. J., Philips F. S. Incorporation of metabolites of 2′-fluoro-5-iodo-1-β-D-arabinofuranosylcytosine into deoxyribonucleic acid of neoplastic and normal mammalian tissues. Biochem. Pharmacol. 31:1982;1103-1108.
11. Howell H. G., Brodfuehrer P. R., Brundidge S. P., Benigni D. A., Sapino C. Jr. Antiviral nucleosides A stereospecific, total synthesis of 2′-fluoro-2′-deoxy-β-D-arabinofuranosyl nucleosides . J. Org. Chem. 53:1988;85-88.
12. 11C]-2′-arabino-2′-fluoro-β-5-methyl-uridine (FMAU). J. Label. Compd. Radiopharm. 36:1995;1133-1145.
13. Iwashina T., Tovell D., Xu Li., Tyrrell D. L., Knaus E. E., Wiebe L. I. Synthesis and antiviral activity of IVFRU, a potential probe for the noninvasive diagnosis of herpes simplex encephalitis. Drug Design Deliv. 3:1988;309-321.
14. 125IUdR in mammalian cells Implications of localized energy deposition by Auger processes . Radiat. Res. 109:1987;78-89.
15. 125I in mammalian cells. Radiat. Res. 111:1987;305-318.
16. Kassis A. I., Howell R. W., Sastry K. S. R., Adelstein S. J. Positional effects of Auger decays in mammalian cells in culture. Baverstock K.F., Charlton D.E. DNA Damage by Auger Emitters. 1988;1-13 Taylor and Francis, New York.
17. 123/125I]iodo-2′-deoxyuridine in rat brain tumors Diagnostic and therapeutic implications in humans . Cancer Res. 50:1990;5199-5203.
18. Klecker R. W., Katki A. G., Collins J. M. Toxicity, metabolism, DNA incorporation with lack of repair, and lactate production for 1-(2′-fluoro-2′-deoxy-β-D-arabinofuranosyl)-5-iodouracil in U-937 and MOLT-4 cells. Mol. Pharmacol. 46:1994;1204-1209.
19. Kong X.-B., Scheck A. C., Price R. W., Vidal P. M., Fanucchi M. P., Watanabe K. A., et al. Incorporation and metabolism of 2′-fluoro-5-substituted arabinosyl pyrimidines and their selective inhibition of viral DNA synthesis in herpes simplex virus type 1 (HSV-1)-infected and mock-infected Vero cells. Antiviral Res. 10:1988;153-166.
20. 211At reaction. Appl. Radiat. Isot. 47:1996;135-143.
21. 211At]astato-2′-deoxyuridine in human cancer cells. Int. J. Radiat. Oncol. Biol. Phys. 72:1997;79-90.
22. Ma T., Pai S. B., Shu Y. L., Lin J. S., Shanmuganathan K., Du J., et al. Structure-activity relationships of 1-(2-deoxy-2-fluoro-β-L-arabinofuranosyl)pyrimidine nucleosides as anti-hepatitis B virus agents. J. Med. Chem. 39:1996;2835-2843.
23. Mariani G., Cei A., Collecchi P., Baranowska-Kortylewicz J., Van den Abbeele A. D., Di Luca L., et al. Tumor targeting in vivo and metabolic fate of 5-[iodine-125]iodo-2′-deoxyuridine following intratumoral injection in patients with colorectoral cancer. J. Nucl. Med. 34:1993;1175-1183.
24. McKenzie R., Fried M. W., Sallie R., Conjeevaram H., Di Bisceglie A. M., Park Y., et al. Hepatic failure and lactic acidosis due to fialuridine (FIAU), an investigational nucleoside analogue for chronic hepatitis B. N. Engl. J. Med. 333:1995;1099-1105.
25. 82Br-labelled 5-halo-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracils. Appl. Radiat. Isot. 37:1986;901-905.
26. Prusoff W. Incorporation of iododeoxyuridine, an analog of thymidine, into mammalian deoxyribounucleic acid. Fed. Proc. 18:1959;305.
27. Richardson F. C., Engelhardt J. A., Bowsher R. R. Fialuridine accumulates in DNA of dogs, monkeys, and rats following long-term oral administration. Proc. Natl. Acad. Sci. USA. 91:1994;12003-12007.
28. 211At decay. Radiochimica Acta. 47:1989;87-89.
29. Tjuvajev J., Muraki A., Ginos J., Berk J., Koutcher J., Ballon D., et al. Iododeoxyuridine uptake and retention as a measure of tumor growth. J. Nucl. Med. 34:1993;1152-1162.
30. Tjuvajev J., Macapinlac H. A., Daghighian F., Scott A. M., Ginos J. Z., Finn R. D., et al. Imaging of brain tumor proliferative activity with iodine-131-iododeoxyuridine. J. Nucl. Med. 35:1994;1407-1417.
31. Tjuvajev J. G., Stockhammer G., Desai R., Uehara H., Watanabe K., Gansbacher B., et al. Imaging the expression of transfected genes. in vivo. Cancer Res. 55:1995;6126-6132.
32. Tjuvajev J. G., Finn R., Watanabe K., Joshi R., Oku T., Kennedy J., et al. Noninvasive imaging of herpes virus thymidine kinase gene transfer and expression A potential method for monitoring clinical gene therapy . Cancer Res. 56:1996;4087-4095.
33. Usuki K., Saras J., Waltenberger J., Miyazono K., Pierce G., Thomason A., et al. Platelet-derived endothelial cell growth factor has thymidine phosphorylase activity. Biochem. Biophys. Res. Commun. 184:1992;1311-1316.
34. Van den Abbeele A. D., Tutrone R. F., Berman R. M., Baranowska-Kortylewicz J., Barclay P. D., Richie J. P., et al. Tumor-targeting potential of radioiodinated iododeoxyuridine in bladder cancer. J. Nucl. Med. 37:1996;315-320.
35. 211At]Astato-2′-deoxyuridine, an α-particle emitting endoradiotherapeutic agent undergoing DNA incorporation. Cancer Res. 56:1996;1204-1209.
36. Watanabe K. A., Reichman U., Hirota K., Lopez C., Fox J. J. Nucleosides 110. Synthesis and antiherpes virus activity of some 2′-fluoro-2′-deoxyarabinofuranosylpyrimidine nucleosides . J. Org. Chem. 22:1979;21-24.
37. 2 fragments with the alpha particle emitting nuclide astatine-211 Preservation of immunoreactivity and in vivo localizing capacity . Proc. Natl. Acad. Sci. USA. 86:1989;7149-7153.