Structural characterization of metabolites of the X-ray contrast agent iopromide in activated sludge using ion trap mass spectrometry

Abstract

Identification of degradation products of environmental contaminants is a challenging task because not only are they present in very low concentrations but they are also mixed with complex matrixes that interfere with detection. This work illustrates a simple approach using ion trap mass spectrometry combined with H/D-exchange experiments to elucidate the structures of iopromide metabolites formed during biodegradation in activated sludge. Iopromide is an X-ray contrast agent that has been detected frequently in effluents of wastewater treatment plants and in surface waters due to its persistence and high usage. Three metabolites produced by oxidation of the primary alcohols (forming carboxylates) on the side chains of iopromide were identified in a batch reactor with mixed liquor from a conventional activated sludge. Derivatization of the carboxylic acid to form a methyl ester and interpretation of the MS2 data of this derivative aided in the confirmation of the identities of these metabolites. Furthermore, one metabolite formed by dehydroxylation at the two side chains was identified in a batch reactor with mixed liquor from a nitrifying activated sludge. The MS2 fragmentation pattern of iopromide and its metabolites revealed that the iodinated ring remains intact and that minor transformations in the structure occur during biodegradation of iopromide in biological wastewater treatment plants.