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Preparation of 5-[131I]iodo- and 5-[211At]astato-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl) uracil by a halodestannylation reaction.

Publication ,  Journal Article
Vaidyanathan, G; Zalutsky, MR
Published in: Nucl Med Biol
July 1998

To circumvent the in vivo instability of 5-iodo-2'-deoxyuridine (IUdR), a 2'-fluorine-substituted analogue, 5-iodo-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)uracil (FIAU) recently has been introduced. To facilitate the preparation of radioiodinated FIAU as well as its astatinated analogue, a tin precursor, 5-trimethylstannyl-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)ura cil (FTAU) was synthesized. Both [125/131I]FIAU and 5-[211At]astato-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)uracil (FAAU) were prepared from FTAU in more than 85% radiochemical yield under mild conditions. The in vitro serum stability of both fluorine-substituted derivatives was higher than that of the corresponding unsubstituted parents. The enhanced stability of fluorinated derivatives was even more apparent in whole blood. The uptake of [125I]FIAU in D-247 MG human glioma cells in vitro was 20-fold higher than that of [125I]IUdR over an activity concentration range of 5-100 kBq/mL; the uptake of FAAU was not significantly different from that of 5-[211At]astato-2'-deoxyuridine (AUdR). Accumulation of radioiodine in mouse thyroid in vivo with [131I]FIAU was fivefold lower than [125I]IUdR, indicating that the former was less susceptible to deiodination. The tissue uptake of FAAU was similar to that reported for AUdR.

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Published In

Nucl Med Biol

DOI

ISSN

0969-8051

Publication Date

July 1998

Volume

25

Issue

5

Start / End Page

487 / 496

Location

United States

Related Subject Headings

  • Tumor Cells, Cultured
  • Tissue Distribution
  • Tin
  • Radiopharmaceuticals
  • Nuclear Medicine & Medical Imaging
  • Mice
  • Isotope Labeling
  • Iodine Radioisotopes
  • Indicators and Reagents
  • Humans
 

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Vaidyanathan, G., & Zalutsky, M. R. (1998). Preparation of 5-[131I]iodo- and 5-[211At]astato-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl) uracil by a halodestannylation reaction. Nucl Med Biol, 25(5), 487–496. https://doi.org/10.1016/s0969-8051(98)00004-3
Vaidyanathan, G., and M. R. Zalutsky. “Preparation of 5-[131I]iodo- and 5-[211At]astato-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl) uracil by a halodestannylation reaction.Nucl Med Biol 25, no. 5 (July 1998): 487–96. https://doi.org/10.1016/s0969-8051(98)00004-3.
Vaidyanathan, G., and M. R. Zalutsky. “Preparation of 5-[131I]iodo- and 5-[211At]astato-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl) uracil by a halodestannylation reaction.Nucl Med Biol, vol. 25, no. 5, July 1998, pp. 487–96. Pubmed, doi:10.1016/s0969-8051(98)00004-3.
Journal cover image

Published In

Nucl Med Biol

DOI

ISSN

0969-8051

Publication Date

July 1998

Volume

25

Issue

5

Start / End Page

487 / 496

Location

United States

Related Subject Headings

  • Tumor Cells, Cultured
  • Tissue Distribution
  • Tin
  • Radiopharmaceuticals
  • Nuclear Medicine & Medical Imaging
  • Mice
  • Isotope Labeling
  • Iodine Radioisotopes
  • Indicators and Reagents
  • Humans