Synthesis and biologic study of IV-14, a new ribonucleoside radiotracer for tumor visualization

Journal of Nuclear Medicine

Volumn 50, Issue 11, 2009, Pages 1895-1903

  Zlatopolskiy, Boris D ^a   Morgenroth, Agnieszka ^a   Kunkel, Falk H G ^a   Urusova, Elizaveta A ^a   Dinger, Cornelia ^a   Kull, Thomas ^a   Lepping, Christian ^a   Reske, Sven N ^a  

^a UNIVERSITY OF ULM   (Germany)

Author keywords

Ribonucleosides; Tumor targeting; Uridine cytidine kinase 2

Indexed keywords

3' (2 IODOVINYL)URIDINE I 123; 3' (2 IODOVINYL)URIDINE I 131; 3' (ETHYNYL)URIDINE; 3' (TRIBUTYLSTANNYLVINYL)URIDINE; IDOXURIDINE I 131; IODIDE I 123; NUCLEOSIDE TRANSPORTER; RADIOACTIVE IODINE; RIBONUCLEOSIDE; THYMIDINE PHOSPHORYLASE; TOSYLCHLORAMIDE SODIUM; TRACER; UNCLASSIFIED DRUG; URIDINE; URIDINE KINASE; URIDINE PHOSPHORYLASE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CAMERA; CANCER CELL CULTURE; CELL PROLIFERATION; CELL STRAIN HL 60; CELLULAR DISTRIBUTION; COLON; CONTROLLED STUDY; DRUG DEGRADATION; DRUG RETENTION; DRUG STABILITY; DRUG UPTAKE; FEMALE; HUMAN; HUMAN CELL; IN VIVO STUDY; INCUBATION TIME; IODINATION; LIVER; MALE; METABOLISM; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; RADIOACTIVITY; RNA SYNTHESIS; SCID MOUSE; SCINTIGRAPHY; SERUM; SMALL INTESTINE; SPLEEN; STOMACH; TUMOR; WESTERN BLOTTING; XENOGRAFT;

ANIMALS; BIOLOGICAL TRANSPORT; CELL LINE, TUMOR; CELL TRANSFORMATION, NEOPLASTIC; FEMALE; HUMANS; INTRACELLULAR SPACE; IODINE RADIOISOTOPES; MALE; MICE; NEOPLASMS; RADIOACTIVE TRACERS; RADIOCHEMISTRY; THYMIDINE PHOSPHORYLASE; TIME FACTORS; TISSUE DISTRIBUTION; URIDINE; URIDINE KINASE; URIDINE PHOSPHORYLASE; VINYL COMPOUNDS;

EID: 70350741386     PISSN: 01615505     EISSN: None     Source Type: Journal    
DOI: 10.2967/jnumed.109.065623     Document Type: Article

References (34)

1. Wiebe LI. Applications of nucleoside-based molecular probes for the in vivo assessment of tumor biochemistry using positron emission tomography (PET). Braz Arch Biol Technol. 2007;50:445-459.
2. Mercer JR. Molecular imaging agents for clinical positron emission tomography in oncology other than fluorodeoxyglucose (FDG): applications, limitations and potential. J Pharm Pharm Sci. 2007;10:180-202.
3. 125I. J Hell Nucl Med. 2004;7:111-116.
4. Toyohara J, Fujibayashi Y. Trends in nucleoside tracers for PET imaging of cell proliferation. Nucl Med Biol. 2003;30:681-685. (Pubitemid 37123124)
5. 18F] fluorodeoxythymidine. Clin Cancer Res. 2008;14:2970-2977.
6. 3H- deoxythymidine in tumor-bearing rats and mice. Eur J Nucl Med. 1985;10:39-44.
7. Takatori S, Kanda H, Takenaka K, et al. Antitumor mechanisms and metabolism of the novel antitumor nucleoside analogues, 1-(3-C-ethynyl-β-D- ribo-pentofuranosyl) cytosine and 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl) uracyl. Cancer Chemother Pharmacol. 1999;44:97-104.
8. Bayés M, Rabasseda X. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008;30:67-79.
9. Yokogawa T, Naito T, Kanda H. Inhibitory mechanisms of 1-(3-C-ethynyl-β-Dribo- pentofuranosyl)uracyl (EUrd) on RNA synthesis. Nucleosides Nucleotides Nucleic Acids. 2005;24:227-232. (Pubitemid 40604862)
10. Shimamoto Y, Kazuno H, Murakami Y, et al. Cellular and biochemical mechanisms of the resistance of human cancer cells to a new anticancer ribonucleoside, TAS-106. Jpn J Cancer Res. 2002;93:445-452. (Pubitemid 34506255)
11. Van Rompay AR, Norda A, Lindén K, Johansson M, Karlsson A. Phosphorylation of uridine and cytidine nucleoside analogs by two human uridine-cytidine kinases. Mol Pharmacol. 2001;59:1181-1186. (Pubitemid 32381598)
12. Murata D, Endo Y, Obata T, et al. A crucial role of uridine/cytidine kinase 2 in antitumor activity of 3′-ethynyl nucleosides. Drug Metab Dispos. 2004;32:1178-1182. (Pubitemid 39287593)
13. Ozaki K, Kuroki T, Hayashi S, Nakamura Y. Isolation of three testis-specific genes (TSA303, TSA806, TSA903) by a differential mRNA display method. Genomics. 1996;36:316-319. (Pubitemid 26307494)
14. Jung PMJ, Burger A, Biellmann J. Diastereofacial selective addition of ethynylcerium reagent and Barton-McCombie reaction as the key steps for the synthesis of C-3′-etynylribonucleosides and of C-3′-etynyl-2′- deoxyribonucleosides. J Org Chem. 1997;62:8309-8314.
15. Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 1976;72:248-254.
16. 125I- iodo-4′-thio-2′-deoxyuridine as a potential iodinated proliferation marker. J Nucl Med. 2002;43:1218-1226.
17. Jamieson GP, Brocklebank AM, Snook MB, et al. Flow cytometric quantitation of nucleoside transporter sites on human leukemic cells. Cytometry. 1993;14: 32-38.
18. Zhang HX, Guibe F, Balavoine G. Palladium- and molybdenum-catalyzed hydrostannation of alkynes: a novel access to regio- and stereodefined vinylstannanes. J Org Chem. 1990;55:1857-1867.
19. Visser F, Sun L, Damaraju V, et al. Residues 334 and 338 in transmembrane segment 8 of human equilibrative nucleoside transporter 1 are important determinants of inhibitor sensitivity, protein folding, and catalytic turnover. J Biol Chem. 2007;282:14148-14157. (Pubitemid 47100457)
20. Reske SN, Deisenhofer S, Glatting G, et al. 123I-ITdU-mediated nanoirradiation of DNA efficiently induces cell kill in HL60 leukemia cells and in doxorubicin-, β-, or γ-radiation-resistant cell lines. J Nucl Med. 2007;48:1000-1007. (Pubitemid 46909930)
21. 125I]iododeoxyuridine under thymidine synthesis blocking in human glioblastoma xenografts. Int J Cancer. 2004;110:145-149.
22. Young JD, Yao SYM, Sun L, Cass CE, Baldwin SA. Human equilibrative nucleoside transporter (ENT) family of nucleoside and nucleobase transporter proteins. Xenobiotica. 2008;38:995-1021.
23. Reichard P, Sköld O. Enzymes of uracil metabolisms in the Ehrlich ascites tumour in mammalian liver. Biochim Biophys Acta. 1958;28:376-385.
24. Hattori H, Nozawa E, Iino T, et al. Nucleosides and nucleotides. 175. Structural requirements for the sugar moiety for the antitumor activities of new nucleoside antimetabolites, 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl) cytosine and -uracil. J Med Chem. 1998;41:2892-2902.
25. el Kouni MH, el Kouni MM, Naguib FNM. Differences in activities and substrate specificity of human and murine pyrimidine nucleoside phosphorylases: implications for chemotherapy with 5-fluoropyrimidines. Cancer Res. 1993;53:3687-3693.
26. Temmink OH, de Bruin M, Laan AC, et al. The role of thymidine phosphorylase and uridine phosphorylase in (fluoro)pyrimidine metabolism in peripheral blood mononuclear cells. Int J Biochem Cell Biol. 2006;38:1759-1765. (Pubitemid 43947657)
27. Zhang Y, Rapa JJ, Inoue Y, Hayhurst GP, Gonzalez FJ, Mangelsdorf DJ. Identification of a liver-specific uridine phosphorylase that is regulated by multiple lipid-sensing nuclear receptors. Mol Endocrinol. 2004;18:851-862. (Pubitemid 38429477)
28. Lazarowski ER, Boucher RC, Harden TK. Mechanisms of release of nucleotides and integration of their action as P2X- and P2Y-receptor activating molecules. Mol Pharmacol. 2003;64:785-795.
29. Guo Y, Köck K, Ritter CA et al. Expression of ABCC-type nucleotide exporters in blasts of adult acute myeloid leukemia: relation to long-term survival. Clin Cancer Res. 2009;15:1762-1769.
30. Reid G, Wielinga P, Zelcer N, et al. Characterization of the transport of nucleoside analog drugs by the human multidrug resistance proteins MRP4 and MRP5. Mol Pharmacol. 2003;63:1094-1103. (Pubitemid 36529928)
31. Failer BU, Braun N, Zimmermann H. Cloning, expression, and functional characterization of a Ca2+-dependent endoplasmic reticulum nucleoside diphosphatase. J Biol Chem. 2002;277:36978-36986.
32. Hunsucker SA, Mitchell BS, Spychala J. The 5′-nucleotidases as regulators of nucleotide and drug metabolism. Pharmacol Ther. 2005;107:1-30. (Pubitemid 40800406)
33. Paproski RJ, Ng AML, Yao SYM, Graham K, Young JD, Cass CE. The role of human nucleoside transporters in uptake of 3′-deoxy-3′- fluorothymidine. Mol Pharmacol. 2008;74:1372-1380.
34. Kong W, Engel K, Wang J. Mammalian nucleoside transporters. Curr Drug Metab. 2004;5:63-84.