Identification of transformation products from β‐blocking agents formed in wetland microcosms using LC‐Q‐ToF

Svan, Alfred; Hedeland, Mikael; Arvidsson, Torbjörn; Jasper, Justin T.; Sedlak, David L.; Pettersson, Curt

doi:10.1002/jms.3737

Cited by 12 publications

(10 citation statements)

References 31 publications

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“…Most metoprolol transformation products were identified previously during reverse osmosis retentate electrolysis 11 or other treatment processes. 12,13 Some propranolol transformation products observed in this study have been reported previously, [14][15][16][17] Identified ciprofloxacin transformation products were typically transformed at the piperazine group rather than chlorinated ( Figures SI 12d, 13), as previously observed during ciprofloxacin reaction with FAC and ClO 2 . 1,18 Trimethoprim was transformed into a variety of hydroxylated and chlorinated transformation products, some of which have been identified during treatment using ferrate, 19 activated sludge, 20 and FAC.…”

Section: S6supporting

confidence: 83%

Electrochemical Transformation of Trace Organic Contaminants in Latrine Wastewater

Jasper

Shafaat

Hoffmann

2016

Environ. Sci. Technol.

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Solar-powered electrochemical systems have shown promise for onsite wastewater treatment in regions where basic infrastructure for conventional wastewater treatment is not available. To assess the applicability of these systems for trace organic contaminant treatment, test compound electrolysis rate constants were measured in authentic latrine wastewater using mixed-metal oxide anodes coupled with stainless steel cathodes. Complete removal of ranitidine and cimetidine was achieved within 30 min of electrolysis at an applied potential of 3.5 V (0.7 A L −1 ). Removal of acetaminophen, ciprofloxacin, trimethoprim, propranolol, and carbamazepine (>80%) was achieved within 3 h of electrolysis. Oxidation of ranitidine, cimetidine, and ciprofloxacin was primarily attributed to reaction with NH 2 Cl. Transformation of trimethoprim, propranolol, and carbamazepine was attributed to direct electron transfer and to reactions with surface-bound reactive chlorine species. Relative contributions of aqueous phase •OH, •Cl, •Cl 2 − , HOCl/OCl − , and Cl 2 were determined to be negligible based on measured second-order reaction rate constants, probe compound reaction rates, and experiments in buffered Cl − solutions. Electrical energy per order of removal (E EO ) increased with increasing applied potentials and current densities. Test compound removal was most efficient at elevated Cl − concentrations present when treated wastewater is recycled for use as flushing water (i.e., ∼ 75 mM Cl − ; E EO = 0.2−6.9 kWh log −1 m −3 ). Identified halogenated and oxygenated electrolysis products typically underwent further transformations to unidentifiable products within the 3 h treatment cycle. Identifiable halogenated byproduct formation and accumulation was minimized during electrolysis of wastewater containing 75 mM Cl − .

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Section: S6supporting

confidence: 83%

Electrochemical Transformation of Trace Organic Contaminants in Latrine Wastewater

Jasper

Shafaat

Hoffmann

2016

Environ. Sci. Technol.

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“…It is important to recognize that these transformation products could be more stable than the parent compound and may pose a risk to the environment (Boxall et al ). For atenolol, based on previous work, the observed dissipation may be explained by the conversion of the parent molecule to metoprolol acid, which is comparatively more stable in water–sediment systems than atenolol (Svan et al ).…”

Section: Resultsmentioning

confidence: 87%

Factors affecting the dissipation of pharmaceuticals in freshwater sediments

Al-Khazrajy

Bergström

Boxall

2017

Enviro Toxic and Chemistry

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Degradation is one of the key processes governing the impact of pharmaceuticals in the aquatic environment. Most studies on the degradation of pharmaceuticals have focused on soil and sludge, with fewer exploring persistence in aquatic sediments. We investigated the dissipation of 6 pharmaceuticals from different therapeutic classes in a range of sediment types. Dissipation of each pharmaceutical was found to follow first‐order exponential decay. Half‐lives in the sediments ranged from 9.5 (atenolol) to 78.8 (amitriptyline) d. Under sterile conditions, the persistence of pharmaceuticals was considerably longer. Stepwise multiple linear regression analysis was performed to explore the relationships between half‐lives of the pharmaceuticals, sediment physicochemical properties, and sorption coefficients for the compounds. Sediment clay, silt, and organic carbon content and microbial activity were the predominant factors related to the degradation rates of diltiazem, cimetidine, and ranitidine. Regression analysis failed to highlight a key property which may be responsible for observed differences in the degradation of the other pharmaceuticals. The present results suggest that the degradation rate of pharmaceuticals in sediments is determined by different factors and processes and does not exclusively depend on a single sediment parameter. Environ Toxicol Chem 2018;37:829–838. © 2017 SETAC

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“…Interestingly, although α-HMPLA and DMPLD were only simultaneously observed for Haematococcus pluvialis , DMPLA was detected for all the four microalgae species, suggesting that while different functional enzymes may be involved in MPL degradation among the four microalgae species, they generally oxidized MPL into α-HMPLA and MPLA, and then into DMPLA. Despite the discovery of the key role which MPLA played in MPL degradation, it has seldom been reported as a MPL intermediate in previous studies ( Murthy et al, 1990 ; Boralli et al, 2005 ; Rubirola et al, 2014 ; Svan et al, 2016 ). A recent study in MPL degradation identified MPLA and DMPLA as TPs of MPL in soil, but no other TPs were found in the study ( Koba et al, 2016 ).…”

Section: Resultsmentioning

confidence: 94%

“…α-HMPL, MPLA, and O-DMPL has been reported to be the three main metabolites of MPL in mammals ( Murthy et al, 1990 ; Boralli et al, 2005 ). Recently, the occurrence and generation of the three metabolites were observed in activated sludge ( Rubirola et al, 2014 ) and wetland microcosms ( Svan et al, 2016 ). Other TPs including 4-(2-hydroxy-3-(isopropylamino)propoxy)phenol and 1-(4-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)-2-methoxyethanone ( Rubirola et al, 2014 ), as well as N -de-isopropylmetoprolol and deaminated metoprolol ( Svan et al, 2016 ) were also reported; however, these four TPs were not detected in this study.…”

Section: Resultsmentioning

confidence: 99%

“…Recently, the occurrence and generation of the three metabolites were observed in activated sludge ( Rubirola et al, 2014 ) and wetland microcosms ( Svan et al, 2016 ). Other TPs including 4-(2-hydroxy-3-(isopropylamino)propoxy)phenol and 1-(4-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)-2-methoxyethanone ( Rubirola et al, 2014 ), as well as N -de-isopropylmetoprolol and deaminated metoprolol ( Svan et al, 2016 ) were also reported; however, these four TPs were not detected in this study. Our study demonstrated that MPL could also be transformed into α-HMPL, MPLA, and O-DMPL by microalgae species such as Scenedesmus quadricauda Breb and Haematococcus pluvialis .…”

Section: Resultsmentioning

confidence: 99%

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Identification of Enantiomeric Byproducts During Microalgae-Mediated Transformation of Metoprolol by MS/MS Spectrum Based Networking

Hsu

et al. 2018

Front. Microbiol.

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Metoprolol (MPL) is a chiral β-blocker ubiquitously detected in various environments due to its low to moderate removal in wastewater treatment plants. This study was conducted to test the potential of using microalgae to degrade emerging contaminant MPL and to characterize the enantiomeric enrichment during MPL degradation by microalgae. The results showed that PO43−- P, NO3−- N and MPL could be simultaneously removed in the synthetic effluent by the targeted microalgae species, indicating microalgae were promising in wastewater treatment. Stereoselectivity was observed during MPL degradation by microalgae, with R-form enrichment. A marginal linear relationship between MPL degradation and enantiomeric enrichment was observed, implying that the enantiomeric tool, used as a quantitative indicator of biodegradation, could possibly be applied in MPL degradation by microalgae. An efficient liquid chromatograph tandem high resolution mass spectrometry (LC-HRMS/MS) chiral analytical method was developed to identify transformation products (TPs). The results showed that MS/MS spectral similarity networking could be used as a powerful tool to quickly identify unknown TPs. A total of 6 pairs of chiral TPs were identified, among which two new TPs of MPL including hydroxy{4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl}acetic acid (α-HMPLA) and 4-[2-Hydroxy-3-(isopropylamino)propoxy]benzaldehyde (DMPLD) were firstly reported, and proposed transformation pathways of MPL by microalgae were given. Considering the paired TPs detected and that the degradation of the two enantiomers followed first order kinetics, the two enantiomers likely had the same degradation mechanism.

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Identification of transformation products from β‐blocking agents formed in wetland microcosms using LC‐Q‐ToF

Cited by 12 publications

References 31 publications

Electrochemical Transformation of Trace Organic Contaminants in Latrine Wastewater

Electrochemical Transformation of Trace Organic Contaminants in Latrine Wastewater

Factors affecting the dissipation of pharmaceuticals in freshwater sediments

Identification of Enantiomeric Byproducts During Microalgae-Mediated Transformation of Metoprolol by MS/MS Spectrum Based Networking

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