Rapid radiosynthesis of [11C] and [14C]azelaic, suberic, and sebacic acids for in vivo mechanistic studies of systemic acquired resistance in plants

Marcel Best, Andrew N. Gifford, Sung Won Kim, Ben Babst, Markus Piel, Frank Rösch, Joanna S. Fowler

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

A recent report that the aliphatic dicarboxylic acid, azelaic acid (1,9-nonanedioic acid) but not related acids, suberic acid (1,8-octanedioic acid) or sebacic (1,10-decanedioic acid) acid induces systemic acquired resistance to invading pathogens in plants stimulated the development of a rapid method for labeling these dicarboxylic acids with 11C and 14C for in vivo mechanistic studies in whole plants. 11C-labeling was performed by reaction of ammonium [ 11C]cyanide with the corresponding bromonitrile precursor followed by hydrolysis with aqueous sodium hydroxide solution. Total synthesis time was 60min. Median decay-corrected radiochemical yield for [11C]azelaic acid was 40% relative to trapped [11C]cyanide, and specific activity was 15GBq/μmol. Yields for [11C]suberic and sebacic acids were similar. The 14C-labeled version of azelaic acid was prepared from potassium [14C]cyanide in 45% overall radiochemical yield. Radiolabeling procedures were verified using 13C-labeling coupled with 13C-NMR and liquid chromatography-mass spectrometry analysis. The 11C and 14C-labeled azelaic acid and related dicarboxylic acids are expected to be of value in understanding the mode-of-action, transport, and fate of this putative signaling molecule in plants.

Original languageEnglish
Pages (from-to)39-43
Number of pages5
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume55
Issue number1
DOIs
StatePublished - Jan 2012
Externally publishedYes

Keywords

  • 1,9-nonanedioic acid
  • azelaic acid
  • plant hormone
  • plant signaling
  • systemic acquired resistance

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