Vinylstannylated Alkylating Agents as Prosthetic Groups for Radioiodination of Small Molecules: Design, Synthesis, and Application to Iodoallyl Analogs of Spiperone and Diprenorphine

John L. Musachio, John R. Lever

Research output: Contribution to journalArticle

Abstract

The preparation and synthetic utility of p-toluenesulfonate esters of (E)-and (Z)-3-(tri-n-butylstannyl)-prop-2-en-l-ol as bifunctional reagents for radioiodination are described. These vinylstannylated alkylating agents are prepared in two steps from propargyl alcohol, and readily couple with nucleophilic functionality (amide nitrogen, secondary amine, tertiary alcohol) in good yields (48-95 %) to provide derivatives of the neuroreceptor ligands spiperone and diprenorphine. Regio-and stereospecific radioiododestannylation with retention of configuration occurs under mild, no-carrier-added conditions to give the corresponding radiolabeled N-or O-iodoallyl analogues in good radiochemical yields (55-95 %) with high specific radioactivities. The methodology is versatile and well-suited to selective labeling of small molecules with radioisotopes of iodine such as 125I or 123I.

Original languageEnglish (US)
Pages (from-to)167-175
Number of pages9
JournalBioconjugate Chemistry
Volume3
Issue number2
DOIs
StatePublished - Mar 1 1992

ASJC Scopus subject areas

  • Biotechnology
  • Bioengineering
  • Biomedical Engineering
  • Pharmacology
  • Pharmaceutical Science
  • Organic Chemistry

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