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Title: Characterization of enalapril and ranitidine chlorination by-products by liquid chromatography/high-resolution mass spectrometry and their toxicity evaluation.
Authors: Quintão, Frederico Jehár Oliveira
Souza, Mariana Pierotti de
Silva, Silvana de Queiroz
Aquino, Sergio Francisco de
Afonso, Robson José de Cássia Franco
Keywords: Enalapril
Disinfection by-products
High-resolution mass spectrometry
Issue Date: 2017
Citation: QUINTÃO, F. J. O. et al. Characterization of enalapril and ranitidine chlorination by-products by liquid chromatography/high-resolution mass spectrometry and their toxicity evaluation. Química Nova, v. 40, p. 745-751, 2017. Disponível em: <>. Acesso em: 05 abr. 2018
Abstract: Due to its low cost, its capability for disinfection and oxidation, chlorination using gaseous chlorine or hypochlorite salts, has also been commonly applied in water treatment plants for oxidation and disinfection purposes. Little is known about the identity and toxicity of by-products resulting from the chlorination of pharmaceutical micropollutants, such as enalapril (ENA) and ranitidine (RAN). ENA and RAN chlorination by-products were characterized in this study by high-performance liquid chromatography coupled to high-resolution mass spectrometry (HPLC/HRMS) and their toxicity were assessed by MTT assay. Chlorination experiments with ENA and RAN solutions (10 mg L-1) indicate degradation efficiencies of 100% for both compounds after only 5 min of exposure to chlorine at concentration of 9.53 mg Cl2 L-1. On the other hand mineralization rates were lower than 3%, thereby indicating there was accumulation of degradation by-products in all experiments. Mass spectrometric analysis revealed, at all times of reaction after the addition of hypochlorite, the presence of 1-(2-((4-(chlorophenyl)-1-ethoxy-1-oxobutan-2-yl)amino)propanoyl)pyrrolidine-2-carboxylic acid (enalapril by-product) and N-chloro-N-(2-(((chloro-5-((dimethylamino)methyl)furan-2-yl)methyl)sulfinyl)ethyl)-N-methyl-2- nitroethene 1,1-diamine (ranitidine by-product). Despite the formation of oxidized chlorinated by-products in all chlorination assays, the treated solutions were nontoxic to HepG2 cells by the MTT assay. It has been observed that chlorination (10 mg L-1, 5 min) of ENA and RAN solutions exhibited high degradation efficiencies of the target compounds and low mineralization rates. Based on the mass spectrometry data, the routes for ENA and RAN successive oxidation by chlorine has been proposed.
ISSN: 16787064
metadata.dc.rights.license: A Sociedade Brasileira de Química dá permissão à UFOP para reproduzir no RI/UFOP, uma cópia em formato eletrônico dos artigos completos, sem nenhuma edição e/ou modificação, publicados na revista Química Nova, que tenham como autores seus alunos e/ou professores. Fonte: Email do editor de 17 set. 2013.
Appears in Collections:DEQUI - Artigos publicados em periódicos

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