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

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 60 min. Median decay‐corrected radiochemical yield for [11C]azelaic acid was 40% relative to trapped [11C]cyanide, and specific activity was 15 GBq/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. Copyright © 2011 John Wiley & Sons, Ltd.