Preparation of 6-125I-labeled amiloride derivatives

Dan Cassel, Miriam Rotman, Edward J. Cragoe, Peter Igarashi

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Amiloride and certain of its derivatives are effective inhibitors of Na H antiporters and of epithelial Na channels. We describe a simple method for the preparation of a variety of pharmacologically active 6-iodoamiloride derivatives that are labeled with 125I at high specific radioactivity. 6-Dechloroamiloride derivatives (bearing a hydrogen atom instead of the chlorine at the 6 position of the amiloride molecule) are reacted with 125ICl, prepared by the oxidation of the iodide in Na125I preparations. The 125I-labeled derivatives are separated from free 125I by anion exchange chromatography, or purified by thin layer chromatography. Both 6-dechloroamiloride and 5-(N-alkyl)-6-dechloroamiloride derivatives can be labeled by this method, with yields varying between 10 and 70%, depending on the ICl concentration and the structure of the 5-N-alkyl group. Efficient radiolabeling at high specific radioactivity also depends on the use of freshly prepared batches of 125I. Using carrier-free 125I, [125I]6-iodoamiloride and [125I]6-iodo-5-(N-tert-butyl)amiloride were prepared with yields of 27 and 22%, respectively. Potential applications of the 125I-labeled amiloride derivatives include ligand binding and affinity labeling experiments.

Original languageEnglish (US)
Pages (from-to)63-67
Number of pages5
JournalAnalytical Biochemistry
Volume170
Issue number1
DOIs
StatePublished - 1988

Fingerprint

Amiloride
Derivatives
Radioactivity
Epithelial Sodium Channels
Sodium-Hydrogen Antiporter
Chlorine
Iodides
Thin Layer Chromatography
Anions
Chromatography
Hydrogen
Bearings (structural)
Ligands
Thin layer chromatography
Labeling
Atoms
Oxidation
Molecules
6-iodoamiloride
Experiments

Keywords

  • Amiloride
  • iodine monochloride
  • Na channels
  • Na H exchange
  • radioiodination
  • transport

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics
  • Molecular Biology

Cite this

Cassel, D., Rotman, M., Cragoe, E. J., & Igarashi, P. (1988). Preparation of 6-125I-labeled amiloride derivatives. Analytical Biochemistry, 170(1), 63-67. https://doi.org/10.1016/0003-2697(88)90090-5

Preparation of 6-125I-labeled amiloride derivatives. / Cassel, Dan; Rotman, Miriam; Cragoe, Edward J.; Igarashi, Peter.

In: Analytical Biochemistry, Vol. 170, No. 1, 1988, p. 63-67.

Research output: Contribution to journalArticle

Cassel, D, Rotman, M, Cragoe, EJ & Igarashi, P 1988, 'Preparation of 6-125I-labeled amiloride derivatives', Analytical Biochemistry, vol. 170, no. 1, pp. 63-67. https://doi.org/10.1016/0003-2697(88)90090-5
Cassel, Dan ; Rotman, Miriam ; Cragoe, Edward J. ; Igarashi, Peter. / Preparation of 6-125I-labeled amiloride derivatives. In: Analytical Biochemistry. 1988 ; Vol. 170, No. 1. pp. 63-67.
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