Synthesis and characterization of a triazine dendrimer that sequesters iron(III) using 12 desferrioxamine B groups

Jongdoo Lim, Vincent J. Venditto, Eric E. Simanek

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13 Scopus citations


The synthesis of a third generation triazine dendrimer, 1, containing multiple, iron-sequestering desferrioxamine B (DFO) groups is described. Benzoylation of the hydroxamic acid groups of DFO and formation of a reactive dichlorotriazine provide the intermediate for reaction with the second generation dendrimer displaying twelve amines. This strategy further generalizes the 'functional monomer' approach to generate biologically active triazine dendrimers. Dendrimer 1 is prepared in seven steps in 35% overall yield and displays 12 DFO groups making it 56% drug by weight. Spectrophotometric titrations (UV-vis) show that 1 sequesters iron(III) atoms with neither cooperativity nor significant interference from the dendrimer backbone. Evidence from NMR spectroscopy and mass spectrometry reveals a limitation to this functional monomer approach: trace amounts of O-to-N acyl migration from the protected hydroxamic acids to the amine-terminated dendrimer occurs during the coupling step leading to N-benzoylated dendrimers displaying fewer than 12 DFO groups.

Original languageEnglish
Pages (from-to)5749-5753
Number of pages5
JournalBioorganic and Medicinal Chemistry
Issue number15
StatePublished - Aug 1 2010

Bibliographical note

Funding Information:
The authors acknowledge support of the NIH ( R01 NIGMS 65640 ) and the Robert A. Welch Foundation ( A 1439 ).


  • Chelation
  • DFO
  • Dendrimer
  • Iron overload
  • Polymer
  • Synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry


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