Biodegradation of sulfamethoxazole: current knowledge and perspectives

Larcher, Simone; Yargeau, Viviane

doi:10.1007/s00253-012-4326-3

Cited by 113 publications

(41 citation statements)

References 66 publications

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“…33 Currently available experimental evidence is not sufficient to confirm this finding, and further research may be required for the quantification of transformation kinetics in treatment systems (MBRs, biofilms) operating at extended SRT. 244 Retransformation processes were shown to be not significant for CIP fate in biological treatment systems, even though limited empirical evidence in full-scale WWTPs was available to confirm this conclusion. ASM-X predictions allowed estimating the significance of sorbed fractions in influent and effluent solids when determining CIP removal efficiency.…”

Section: Assessment In Wwtpsmentioning

confidence: 99%

Removal of Antibiotics in Biological Wastewater Treatment Systems—A Critical Assessment Using the Activated Sludge Modeling Framework for Xenobiotics (ASM-X)

Polesel

Andersen

Trapp

et al. 2016

Environ. Sci. Technol.

135

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Many scientific studies present removal efficiencies for pharmaceuticals in laboratory-, pilot-, and full-scale wastewater treatment plants, based on observations that may be impacted by theoretical and methodological approaches used. In this Critical Review, we evaluated factors influencing observed removal efficiencies of three antibiotics (sulfamethoxazole, ciprofloxacin, tetracycline) in pilot- and full-scale biological treatment systems. Factors assessed include (i) retransformation to parent pharmaceuticals from e.g., conjugated metabolites and analogues, (ii) solid retention time (SRT), (iii) fractions sorbed onto solids, and (iv) dynamics in influent and effluent loading. A recently developed methodology was used, relying on the comparison of removal efficiency predictions (obtained with the Activated Sludge Model for Xenobiotics (ASM-X)) with representative measured data from literature. By applying this methodology, we demonstrated that (a) the elimination of sulfamethoxazole may be significantly underestimated when not considering retransformation from conjugated metabolites, depending on the type (urban or hospital) and size of upstream catchments; (b) operation at extended SRT may enhance antibiotic removal, as shown for sulfamethoxazole; (c) not accounting for fractions sorbed in influent and effluent solids may cause slight underestimation of ciprofloxacin removal efficiency. Using tetracycline as example substance, we ultimately evaluated implications of effluent dynamics and retransformation on environmental exposure and risk prediction.

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Section: Assessment In Wwtpsmentioning

confidence: 99%

Removal of Antibiotics in Biological Wastewater Treatment Systems—A Critical Assessment Using the Activated Sludge Modeling Framework for Xenobiotics (ASM-X)

Polesel

Andersen

Trapp

et al. 2016

Environ. Sci. Technol.

135

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“…Contamination with sulfonamides poses environmental concern due to the potential development and dissemination of antibiotic resistances (7). Despite their ubiquity, their microbial metabolism and ultimate fate in the environment thereof are poorly understood.…”

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confidence: 99%

ipso -Hydroxylation and Subsequent Fragmentation: a Novel Microbial Strategy To Eliminate Sulfonamide Antibiotics

Ricken

Corvini

Cichocka

et al. 2013

Appl Environ Microbiol

105

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f Sulfonamide antibiotics have a wide application range in human and veterinary medicine. Because they tend to persist in the environment, they pose potential problems with regard to the propagation of antibiotic resistance. Here, we identified metabolites formed during the degradation of sulfamethoxazole and other sulfonamides in Microbacterium sp. strain BR1. Our experiments showed that the degradation proceeded along an unusual pathway initiated by ipso-hydroxylation with subsequent fragmentation of the parent compound. The NADH-dependent hydroxylation of the carbon atom attached to the sulfonyl group resulted in the release of sulfite, 3-amino-5-methylisoxazole, and benzoquinone-imine. The latter was concomitantly transformed to 4-aminophenol. Sulfadiazine, sulfamethizole, sulfamethazine, sulfadimethoxine, 4-amino-N-phenylbenzenesulfonamide, and N-(4-aminophenyl)sulfonylcarbamic acid methyl ester (asulam) were transformed accordingly. Therefore, ipso-hydroxylation with subsequent fragmentation must be considered the underlying mechanism; this could also occur in the same or in a similar way in other studies, where biotransformation of sulfonamides bearing an amino group in the para-position to the sulfonyl substituent was observed to yield products corresponding to the stable metabolites observed by us. Sulfonamides are widely used as antibiotics, antidiabetics, diuretics, antivirals, and anticancer agents (1-4), and thus, large amounts of these compounds enter the environment every year (5, 6). Contamination with sulfonamides poses environmental concern due to the potential development and dissemination of antibiotic resistances (7). Despite their ubiquity, their microbial metabolism and ultimate fate in the environment thereof are poorly understood.Several studies showed that sulfamethoxazole (SMX) (Fig. 1a), an important representative of sulfonamide compounds, undergoes partial degradation in wastewater treatment plants under aerobic and anaerobic conditions (8-11). We recently demonstrated that Microbacterium sp. strain BR1, a Gram-positive bacterium isolated from a membrane bioreactor treating effluent contaminated by several pharmaceuticals, was capable of mineralizing the 14 C-labeled aniline moiety of SMX when the latter was supplied as the sole carbon source (12). This was the first unambiguous indication that sulfonamides are subject to growth-linked metabolism in microorganisms.To our knowledge, Hartig (13) was the first to identify the aminated heteroaromatic side moieties of the sulfonamides SMX and sulfadimethoxine as stable metabolites after biodegradation with activated sludge. This result was recently confirmed by two groups that were able to isolate Microbacterium strains with the ability to degrade the sulfonamides sulfamethazine (SMZ) (14) and sulfadiazine (SDZ) (15). Additionally, both groups identified the aminated heteroaromatic side moieties of the sulfonamide as a stable metabolite after the degradation of the parent compound. Although these stable metabolites were identified, the i...

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“…Laboratory experiments already proved a completely different removal behavior of benzotriazole, 4- and 5-tolyltriazole [11,21] but biodegradation conditions remain rather unclear. SMX, in contrast, showed sometimes an almost complete removal in lab-scale setups inoculated with AS communities and/or mixed cultures under different conditions tested [22,23]. Furthermore, only little information is available on individual organisms being capable of SMX biodegradation as well as biodegradation potential under different redox and nutrient conditions [24-27].…”

Section: Introductionmentioning

confidence: 99%

Screening and monitoring microbial xenobiotics’ biodegradation by rapid, inexpensive and easy to perform microplate UV-absorbance measurements

et al. 2014

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BackgroundEvaluation of xenobiotics biodegradation potential, shown here for benzotriazoles (corrosion inhibitors) and sulfamethoxazole (sulfonamide antibiotic) by microbial communities and/or pure cultures normally requires time intensive and money consuming LC/GC methods that are, in case of laboratory setups, not always needed.ResultsThe usage of high concentrations to apply a high selective pressure on the microbial communities/pure cultures in laboratory setups, a simple UV-absorbance measurement (UV-AM) was developed and validated for screening a large number of setups, requiring almost no preparation and significantly less time and money compared to LC/GC methods. This rapid and easy to use method was evaluated by comparing its measured values to LC-UV and GC-MS/MS results. Furthermore, its application for monitoring and screening unknown activated sludge communities (ASC) and mixed pure cultures has been tested and approved to detect biodegradation of benzotriazole (BTri), 4- and 5-tolyltriazole (4-TTri, 5-TTri) as well as SMX.ConclusionsIn laboratory setups, xenobiotics concentrations above 1.0 mg L-1 without any enrichment or preparation could be detected after optimization of the method. As UV-AM does not require much preparatory work and can be conducted in 96 or even 384 well plate formats, the number of possible parallel setups and screening efficiency was significantly increased while analytic and laboratory costs were reduced to a minimum.

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Biodegradation of sulfamethoxazole: current knowledge and perspectives

Cited by 113 publications

References 66 publications

Removal of Antibiotics in Biological Wastewater Treatment Systems—A Critical Assessment Using the Activated Sludge Modeling Framework for Xenobiotics (ASM-X)

Removal of Antibiotics in Biological Wastewater Treatment Systems—A Critical Assessment Using the Activated Sludge Modeling Framework for Xenobiotics (ASM-X)

ipso -Hydroxylation and Subsequent Fragmentation: a Novel Microbial Strategy To Eliminate Sulfonamide Antibiotics

Screening and monitoring microbial xenobiotics’ biodegradation by rapid, inexpensive and easy to perform microplate UV-absorbance measurements

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