Synthesis and radioiodination of some 9-aminoacridine derivatives

Senait Ghirmai, Eskender Mume, Cecile Henssen, Hadi Ghaneolhusseini, Hans Lundqvist, Vladimir Tolmachev, Stefan Sjöberg, Anna Orlova

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

Derivatives of 9-aminoacridine, namely N-[ω-(acridin-9-yl-amino) alkyl]-3-(trimethylstannyl)benzamides (1), where the alkyl group is propyl (1a) and octyl (1b), and 2-(acridin-9-ylamino)-3-(4-hydroxyphenyl)propionic acid (2), have been synthesized with the aim to use them as precursors in the syntheses of radiolabeled DNA intercalators for biological experiments. It was observed that compounds 1a and 1b can exist in two isomeric forms at room temperature. Radioiodination of the two benzamides 1a and 1b was carried out with the Auger-emitting nuclide 125I by exchange of the trimethylstannyl group. The optimal conditions for radioiodination of the octyl derivative 1b were established and the labeling yield was found to be as high as 92%, according to TLC analysis in model experiments. Purification of the radioiodinated products gave radiochemical yields of 56% for the propyl and 74% for the octyl compound. The amino acid 2 was directly labeled with 125I at the ortho position to the hydroxyl group by taking advantage of the activated ring. The experiment afforded a very high labeling yield (92%).

Original languageEnglish
Pages (from-to)3719-3725
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number17
DOIs
Publication statusPublished - 27 Aug 2004
Externally publishedYes

Keywords

  • DNA
  • Intercalations
  • Iodine
  • Labeling
  • Radiochemistry
  • Tautomerism

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis and radioiodination of some 9-aminoacridine derivatives'. Together they form a unique fingerprint.

Cite this