CHARACTERIZATION OF ENALAPRIL AND RANITIDINE CHLORINATION BY-PRODUCTS BY LIQUID CHROMATOGRAPHY/HIGH-RESOLUTION MASS SPECTROMETRY AND THEIR TOXICITY EVALUATION
Autor(a) principal: | |
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Data de Publicação: | 2017 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Química Nova (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422017000700745 |
Resumo: | 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. |
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CHARACTERIZATION OF ENALAPRIL AND RANITIDINE CHLORINATION BY-PRODUCTS BY LIQUID CHROMATOGRAPHY/HIGH-RESOLUTION MASS SPECTROMETRY AND THEIR TOXICITY EVALUATIONenalaprilranitidinehigh-resolution mass spectrometrydisinfection by-productsMTT assayDue 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.Sociedade Brasileira de Química2017-08-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422017000700745Química Nova v.40 n.7 2017reponame:Química Nova (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0100-4042.20170061info:eu-repo/semantics/openAccessQuintão,Frederico Jehár OliveiraSouza,Mariana Pierotti deSilva,Silvana de QueirozAquino,Sérgio FranciscoAfonso,Robson José de Cássia Francoeng2017-09-15T00:00:00Zoai:scielo:S0100-40422017000700745Revistahttps://www.scielo.br/j/qn/ONGhttps://old.scielo.br/oai/scielo-oai.phpquimicanova@sbq.org.br1678-70640100-4042opendoar:2017-09-15T00:00Química Nova (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
CHARACTERIZATION OF ENALAPRIL AND RANITIDINE CHLORINATION BY-PRODUCTS BY LIQUID CHROMATOGRAPHY/HIGH-RESOLUTION MASS SPECTROMETRY AND THEIR TOXICITY EVALUATION |
title |
CHARACTERIZATION OF ENALAPRIL AND RANITIDINE CHLORINATION BY-PRODUCTS BY LIQUID CHROMATOGRAPHY/HIGH-RESOLUTION MASS SPECTROMETRY AND THEIR TOXICITY EVALUATION |
spellingShingle |
CHARACTERIZATION OF ENALAPRIL AND RANITIDINE CHLORINATION BY-PRODUCTS BY LIQUID CHROMATOGRAPHY/HIGH-RESOLUTION MASS SPECTROMETRY AND THEIR TOXICITY EVALUATION Quintão,Frederico Jehár Oliveira enalapril ranitidine high-resolution mass spectrometry disinfection by-products MTT assay |
title_short |
CHARACTERIZATION OF ENALAPRIL AND RANITIDINE CHLORINATION BY-PRODUCTS BY LIQUID CHROMATOGRAPHY/HIGH-RESOLUTION MASS SPECTROMETRY AND THEIR TOXICITY EVALUATION |
title_full |
CHARACTERIZATION OF ENALAPRIL AND RANITIDINE CHLORINATION BY-PRODUCTS BY LIQUID CHROMATOGRAPHY/HIGH-RESOLUTION MASS SPECTROMETRY AND THEIR TOXICITY EVALUATION |
title_fullStr |
CHARACTERIZATION OF ENALAPRIL AND RANITIDINE CHLORINATION BY-PRODUCTS BY LIQUID CHROMATOGRAPHY/HIGH-RESOLUTION MASS SPECTROMETRY AND THEIR TOXICITY EVALUATION |
title_full_unstemmed |
CHARACTERIZATION OF ENALAPRIL AND RANITIDINE CHLORINATION BY-PRODUCTS BY LIQUID CHROMATOGRAPHY/HIGH-RESOLUTION MASS SPECTROMETRY AND THEIR TOXICITY EVALUATION |
title_sort |
CHARACTERIZATION OF ENALAPRIL AND RANITIDINE CHLORINATION BY-PRODUCTS BY LIQUID CHROMATOGRAPHY/HIGH-RESOLUTION MASS SPECTROMETRY AND THEIR TOXICITY EVALUATION |
author |
Quintão,Frederico Jehár Oliveira |
author_facet |
Quintão,Frederico Jehár Oliveira Souza,Mariana Pierotti de Silva,Silvana de Queiroz Aquino,Sérgio Francisco Afonso,Robson José de Cássia Franco |
author_role |
author |
author2 |
Souza,Mariana Pierotti de Silva,Silvana de Queiroz Aquino,Sérgio Francisco Afonso,Robson José de Cássia Franco |
author2_role |
author author author author |
dc.contributor.author.fl_str_mv |
Quintão,Frederico Jehár Oliveira Souza,Mariana Pierotti de Silva,Silvana de Queiroz Aquino,Sérgio Francisco Afonso,Robson José de Cássia Franco |
dc.subject.por.fl_str_mv |
enalapril ranitidine high-resolution mass spectrometry disinfection by-products MTT assay |
topic |
enalapril ranitidine high-resolution mass spectrometry disinfection by-products MTT assay |
description |
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. |
publishDate |
2017 |
dc.date.none.fl_str_mv |
2017-08-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422017000700745 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422017000700745 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.21577/0100-4042.20170061 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Química Nova v.40 n.7 2017 reponame:Química Nova (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Química Nova (Online) |
collection |
Química Nova (Online) |
repository.name.fl_str_mv |
Química Nova (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
quimicanova@sbq.org.br |
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1750318118374211584 |