Radiolabeled biotin amides from triazenyl precursors

Synthesis, binding, and in‐vivo properties

Zbigniew P. Kortylewicz, Janina Baranowska-Kortylewicz, S. James Adelstein, Alice D. Carmel, Amin I. Kassis

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The synthesis of N‐(4‐[127/125/123l]iodobenzyl)biotin amides 4a — 4c performed by the direct decomposition of N‐[4‐(3′,3′‐dimethyltriazenyl)benzyl)biotin amide with sodium iodide in the presence of CF3COOH is described. Iodinated in this way biotin formed a stable complex with avidin (Kd = 2.84 ± 0.45 × 10−15 M, n = 3.9 ± 0.6) which dissociated in the presence of excess native biotin with a rate constant of 0.034 ± 0.006 hr1. Blood clearance studies and the lack of thyroid uptake indicated that this compound was not deiodinated in vivo and behaved in circulation much like native biotin. This aryltriazene precursor method is suitable for labeling with short‐lived radiohalides. It can be used to produce no‐carrier‐added derivatives of biotin for use in biologic studies and assays involving avidin or streptavidin.

Original languageEnglish (US)
Pages (from-to)1129-1146
Number of pages18
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume34
Issue number12
DOIs
StatePublished - Jan 1 1994

Fingerprint

Biotin
Amides
Avidin
Sodium Iodide
Streptavidin
Biological Assay
Labeling
Rate constants
Assays
Thyroid Gland
Blood
Derivatives
Decomposition

Keywords

  • Biodistribution
  • Biotin
  • Iodobenzylbiotin Amides
  • Triazene
  • l‐radioiodination

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Radiology Nuclear Medicine and imaging
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

Cite this

Radiolabeled biotin amides from triazenyl precursors : Synthesis, binding, and in‐vivo properties. / Kortylewicz, Zbigniew P.; Baranowska-Kortylewicz, Janina; Adelstein, S. James; Carmel, Alice D.; Kassis, Amin I.

In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 34, No. 12, 01.01.1994, p. 1129-1146.

Research output: Contribution to journalArticle

Kortylewicz, Zbigniew P. ; Baranowska-Kortylewicz, Janina ; Adelstein, S. James ; Carmel, Alice D. ; Kassis, Amin I. / Radiolabeled biotin amides from triazenyl precursors : Synthesis, binding, and in‐vivo properties. In: Journal of Labelled Compounds and Radiopharmaceuticals. 1994 ; Vol. 34, No. 12. pp. 1129-1146.
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