Synthesis and characterization of nido-carborane-cobalamin conjugates

Harry P.C. Hogenkamp, Douglas A. Collins, David Live, Linda M. Benson, Stephen Naylor

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

Three vitamin B12 (cyanocobalamin) conjugates bearing one nido-carborane molecule or two nido-carborane molecules linked to the propionamide side chains via a four carbon linker have been synthesized. Reaction of o-carboranoylchloride with 1,4-diaminobutane in pyridine produced nido-carboranoyl(4-amidobutyl)amine, which was linked to the b- and d-monocarboxylic acids and the b,d-dicarboxylic acid of cyanocobalamin. Mass spectrometry analysis as well as 11B nuclear magnetic resonance demonstrated that during the reaction of o-carboranonylchloride with diaminobutane one of the boron atoms was eliminated. In vitro biological activity of the cyanocobalamin-nido-carborane conjugates was assessed by the unsaturated vitamin B12 binding capacity assay. When compared with 57Co cyanocobalamin, the biological activity of cyanocobalamin-b-nido-carborane, cyanocobalamin-d-nido-carborane, and cyanocobalamin-b-d-bis-nido-carborane conjugates were 92.93%, 35.75%, and 37.02%, respectively. These findings suggest that the 10B cobalamin conjugates might be useful agents in treating malignant tumors via neutron capture therapy. Copyright (C) 2000 Elsevier Science Inc.

Original languageEnglish (US)
Pages (from-to)89-92
Number of pages4
JournalNuclear Medicine and Biology
Volume27
Issue number1
DOIs
StatePublished - Jan 1 2000

Keywords

  • Boron neutron capture therapy (BNCT)
  • Boronated vitamin B
  • Cyanocobalamin-nido-carborane conjugates
  • Vitamin B

ASJC Scopus subject areas

  • Molecular Medicine
  • Radiology Nuclear Medicine and imaging
  • Cancer Research

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