Enantiomeric fractionation as a tool for quantitative assessment of biodegradation: The case of metoprolol

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

“…However, till now, information concerning the removal of MPL by the microalgae is still limited, not to mention the transformation pathway by the microalgae. Additionally, enantiomeric fraction (EF) of enantiomers is critical to evaluate their susceptibility to biodegradation, and has recently been suggested as predictive tools to elucidate the fate of chiral pharmaceuticals ( Jammer et al, 2014 ; Souchier et al, 2016 ). For instance, a linear relationship was obtained between aerobic biodegradation of MPL and enantiomeric enrichment in wastewater treatment plant through the application of Rayleigh equation ( Souchier et al, 2016 ).…”

“…Additionally, enantiomeric fraction (EF) of enantiomers is critical to evaluate their susceptibility to biodegradation, and has recently been suggested as predictive tools to elucidate the fate of chiral pharmaceuticals ( Jammer et al, 2014 ; Souchier et al, 2016 ). For instance, a linear relationship was obtained between aerobic biodegradation of MPL and enantiomeric enrichment in wastewater treatment plant through the application of Rayleigh equation ( Souchier et al, 2016 ). However, inconsistent results were also reported by Matamoros et al (2009) , who found that the EF value of ibuprofen was not correlated with its removal efficiency due to different enantioselective degradation kinetics under aerobic and anaerobic conditions in the wastewater treatment plant ( Matamoros et al, 2009 ).…”

Occurrence of Chiral Bioactive Compounds in the Aquatic Environment: A Review

“…Metoprolol was determined in influents and effluents of some WWTPs in France [90], being detected in all samples with mean concentrations ranging between 97 and 687 ng/L in influents (close to racemic) and from 18.6 to 157 ng/L in effluents, where EF varied from 0.57 up to 0.70, except in one WWTP effluent (EF = 0.5). The results of that work indicated a (S)-metoprolol enrichment during wastewater treatment in most cases, which extent was dependent on the WWTP [90].…”

“…Since 2010, a trend is being verified for the use of three types of CSPs: protein-based [68,69,[74][75][76][77]81,82,100,101], polysaccharide-based [54,55,78,79,102] and macrocyclic antibiotic-based CSPs [13,26,27,63,64,71-73, 76,78,88,91,103]. The first reports describing the use of macrocyclic antibiotic-based CSPs for environmental analysis were published in 2006-2007 [84,104], but its application was later intensely reported from 2010 [13,26,27,57,[71][72][73]76,78,86,87,90,93,94,103,105]. Other works were published using normal elution mode, namely for the study of beta-blockers in surface waters [78,79] and for the monitoring of enantioselective biodegradation of warfarin in soils [11].…”

“…GC-MS/MS was employed in the first works reporting enantioselective environmental analysis by indirect methods using enantiomerically-pure derivatizing reagents [9,60], or by direct methods using CSPs [61,85]. Despite indirect [70,83] and direct methods [67,80,89] remaining in some studies, LC-MS/MS has been the analytical technique of election for illicit drugs and pharmaceutical while GC-MS and GC-ECD have been the most used for pesticides [13,54,55,57,62,[64][65][66][67][68][69][71][72][73][74][75][76][77][80][81][82]84,87,88,[90][91][92]95,[100][101][102][103][104][105]. Although much less used, LC-DAD, LC-UV and LC-FD detection have been used in some of the studies [11,26,27,…”