Biotransformation of macrolide antibiotics using enriched activated sludge culture: Kinetics, transformation routes and ecotoxicological evaluation

Terzić, Senka; Udikovic-Kolic, Nikolina; Jurina, Tamara; Krizman-Matasic, Ivona; Senta, Ivan; Mihaljević, Ivan; Lončar, Jovica; Smital, Tvrtko; Ahel, Marijan

doi:10.1016/j.jhazmat.2018.01.055

Cited by 78 publications

(40 citation statements)

References 32 publications

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“…The initial activated sludge was unable to degrade macrolide antibiotics at concentration of 1 -10 mg L -1 . After two months of exposure at 10 mg L -1 , the removal efficiency was increased to 99% (Terzic et al, 2018). Accordingly, TrOC-degrading strains have been identified for the removal of previously reported persistent compounds (Moreira et al, 2014;Mulla et al, 2016;Pan et al, 2018;Yu et al, 2007).…”

Section: Introductionmentioning

confidence: 86%

“…Previous studies have demonstrated that long-term exposure of activated sludge microbiome to TrOCs can alter the microbial community and in some cases selectively enrich specific microbes with enhanced affinity for TrOCs biodegradation (Moreira et al, 2014;Navaratna et al, 2012;Qu & Spain, 2010;Terzic et al, 2018;Zhou et al, 2013). An early example was observed for acesulfame (ACE), a synthetic sweetener.…”

Section: Introductionmentioning

confidence: 99%

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Aerobic biotransformation of the antibiotic ciprofloxacin by Bradyrhizobium sp. isolated from activated sludge

Nguyen

2018

Chemosphere

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Ciprofloxacin (CIP) is an antibiotic that is widely used to treat bacterial infections and is poorly biodegraded during wastewater treatment. In this study, a CIP-degrading bacterial strain (GLC_01) was successfully retrieved from activated sludge by enrichment and isolation. The obtained bacterial strain shares over 99% nucleotide identity of the 16S rRNA gene with Bradyrhizobium spp. Results show that Bradyrhizobium sp. GLC_01 degraded CIP via cometabolism with another carbon substrate following a first-order kinetics degradation reaction. CIP degradation by Bradyrhizobium sp. GLC_01 increased when the concentration of the primary carbon source increased. The biodegradability of the primary carbon source also affected CIP degradation. The use of glucose and sodium acetate (i.e. readily biodegradable), respectively, as a primary carbon source enhanced CIP biotransformation, compared to starch (i.e. relatively slowly biodegradable). CIP degradation decreased with the increase of the initial CIP concentration. Over 70% CIP biotransformation was achieved at 0.05 mg L whereas CIP degradation decreased to 26% at 10 mg L. The phylogenetic identification and experimental verification of this CIP-degrading bacterium can lead to a bioengineering approach to manage antibiotics and possibly other persistent organic contaminants during wastewater treatment.

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Section: Introductionmentioning

confidence: 86%

Section: Introductionmentioning

confidence: 99%

Aerobic biotransformation of the antibiotic ciprofloxacin by Bradyrhizobium sp. isolated from activated sludge

Nguyen

2018

Chemosphere

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“…It should be pointed out that pure reference standards of these compounds were not available, which prevented obtaining fully quantitative results. Nevertheless, the media from biotransformation experiments described in Terzic et al (2018) 31 were applied as qualitative standards, providing link to structural information, as well as to retention time data for the additional TPs. The overview of the TPs encompassed by this screening is presented in Table 3.…”

Section: Screening For Additional Transformation Productsmentioning

confidence: 99%

“…25 In our earlier study, novel TPs of AZI and roxythromycin (ROX), formed by microbial phosphorylation, were identified in wastewater effluent of a membrane bioreactor, 30 while a recent study on aerobic biodegradation of AZI, CLA and ERY revealed a number of previously unreported, novel TPs and allowed proposing a general transformation pathways scheme for AZI. 31 In addition, non-target analysis of freshwater sediments polluted by pharmaceutical industry effluent indicated the importance of intermediates in AZI synthesis. 32 In order to address the complexity of macrolidederived compounds, we recently developed a novel quantitative analytical method, comprising parent macrolide antibiotics, their major human metabolites and TPs, as well as by-products from AZI synthesis, in wastewater and river water samples.…”

Section: Introductionmentioning

confidence: 99%

Occurrence and Behavior of Macrolide Antibiotics in Municipal Wastewater Treatment: Possible Importance of Metabolites, Synthesis Byproducts, and Transformation Products

Senta

Kostanjevečki

Krizman-Matasic

et al. 2019

Environ. Sci. Technol.

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A one-year study on the occurrence and fate of macrolide antibiotics and their metabolites, synthesis by-products and transformation products (TPs) was performed in the wastewater treatment plant of the city of Zagreb (Croatia). The target compounds were found in all analyzed influent and effluent samples, with the total concentrations of azithromycin-, clarithromycin-and erythromycin-related compounds reaching up to 25, 12 and 0.25 μg/L, respectively. The most prominent individual constituents were the parent macrolides azithromycin and clarithromycin. However, a substantial contribution of their derivatives, formed by deglycolysation and microbial phosphorylation, was also detected. In addition, widespread presence of several linearized non-target TPs was confirmed for the first time in real wastewater samples by suspect screening analysis. Complex characterization of macrolide-derived compounds enabled decoupling of industrial and therapeutic sources from the insitu transformations. Due to the high inputs, incomplete removal and/or formation of several TPs during the conventional wastewater treatment, the average mass load of azithromycin-related compounds in secondary effluents exceeded 3.0 g/day/1000 inhabitants. This is the first study to reveal the importance of metabolites, by-products and TPs for the overall mass balance of macrolide antibiotics in urban wastewater systems.

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“…The cultures AS-1, AS-2 and AS-3 originated from the aeration tank of the Central wastewater treatment plant of the city of Zagreb and were previously enriched on three different amine-moiety containing compounds: azithromycin (10 mg/L), tramadol (20 mg/L) and MTHD (10 mg/L), respectively. The cultures AS-1 and AS-2 were previously proven to be able to degrade macrolide antibiotics (Terzic et al, 2018) and tramadol (unpublished data), respectively. Before being used in M A N U S C R I P T…”

Section: Selection and Preparation Of Microbial Cultures For Preliminmentioning

confidence: 91%

Biodegradation study of methadone by adapted activated sludge: Elimination kinetics, transformation products and ecotoxicological evaluation

et al. 2019

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The biotransformation study of difficult-to-degrade opioid analgesic methadone (MTHD) was performed by activated sludge culture adapted to high concentration of methadone (10 mg/L).The study included determination of elimination kinetics of the parent compound, taxonomic characterization of microbial culture, identification of biotransformation products (TPs) and assessment of ecotoxicological effects of biotransformation processes. The chemical analyses were performed by ultra-performance liquid chromatography/quadrupole-time-of-flight mass spectrometry, whereas the ecotoxicological assessment was made based on determinations of toxicity to freshwater algae. Changes of the adapted sludge culture during the experiment were followed using the 16S rRNA gene amplicon sequencing. Depending on the experimental conditions, the elimination efficiency of methadone (10 mg/L) varied from 9% to 93% with the corresponding half-lives from 11.4 days and 1.5 days. A significantly faster elimination (t 1/2 from 1.5 days to 5.8 days) was achieved at cometabolic conditions, using glucose-containing media, as compared to the experiments with MTHD as a single organic carbon source (t 1/2 = 11.4 days). Moreover, increased biotransformation rate following the additional supplementation of ammonia, revealed a possible importance of nitrogen availability for the transformation at cometabolic conditions. The elimination of parent compound was associated with the formation of 3 different TPs, two of which were identical to main human metabolites of MTHD, 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine (EDDP) and 2-ethyl-5-methyl-3,3-diphenyl-1-pyrroline (EMDP). EDDP represented over 90% of the total TP concentration at the end of experiment. The biodegradation of MTHD was associated with a pronounced drop in algal toxicity, confirming a rather positive ecotoxicological outcome of the achieved biotransformation processes.

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Biotransformation of macrolide antibiotics using enriched activated sludge culture: Kinetics, transformation routes and ecotoxicological evaluation

Cited by 78 publications

References 32 publications

Aerobic biotransformation of the antibiotic ciprofloxacin by Bradyrhizobium sp. isolated from activated sludge

Aerobic biotransformation of the antibiotic ciprofloxacin by Bradyrhizobium sp. isolated from activated sludge

Occurrence and Behavior of Macrolide Antibiotics in Municipal Wastewater Treatment: Possible Importance of Metabolites, Synthesis Byproducts, and Transformation Products

Biodegradation study of methadone by adapted activated sludge: Elimination kinetics, transformation products and ecotoxicological evaluation

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