ArticleApplied and environmental microbiology2013
Ipso-hydroxylation and subsequent fragmentation: a novel microbial strategy to eliminate sulfonamide antibiotics.
Article in Applied and environmental microbiology, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 144 citations in OpenAlex.
- Biodegradation of sulfonamide antibiotics by a soil bacteria enrichment and the impacts of soil organic matter.Eco-Environment & Health · 2026Article
- Population Dynamics and Cross-Feeding in an Antibiotic-Degrading Synthetic Ecosystem: Insights from Single-Cell Raman Spectroscopy and Stable Isotope Probing.Environmental science & technology letters · 2026Article
- Deciphering the constraints of pure bacterial strains for the complete catabolism of sulfamethoxazole: A proteomic and kinetic study.Biodegradation · 2025Article
- Cross-feeding and co-degradation within a bacterial consortium dominated by challenging-to-cultureApplied and environmental microbiology · 2025Article
- Sulfamethoxazole is Metabolized and Mineralized at Extremely Low Concentrations.Environmental science & technology · 2024Article
- New insights into bioaugmented removal of sulfamethoxazole in sediment microcosms: degradation efficiency, ecological risk and microbial mechanisms.Microbiome · 2024Article
- Metabolic engineering ofMicrobiology spectrum · 2023Article
- Recently evolved combination of unique sulfatase and amidase genes enables bacterial degradation of the wastewater micropollutant acesulfame worldwide.Frontiers in microbiology · 2023Article
- Sulfamethoxazole Enhances Specific Enzymatic Activities under Aerobic Heterotrophic Conditions: A Metaproteomic Approach.Environmental science & technology · 2022Article
- Occurrence of antibiotics and bacterial resistance genes in wastewater: resistance mechanisms and antimicrobial resistance control approaches.World journal of microbiology & biotechnology · 2022Review
- A Review on Microorganisms in Constructed Wetlands for Typical Pollutant Removal: Species, Function, and Diversity.Frontiers in microbiology · 2022Review
- Contrasting Effects of Environmental Concentrations of Sulfonamides on Microbial Heterotrophic Activities in Freshwater Sediments.Frontiers in microbiology · 2021Article
- Enrichment of endophytic Actinobacteria in roots and rhizomes of Miscanthus × giganteus plants exposed to diclofenac and sulfamethoxazole.Environmental science and pollution research international · 2020Article
- Comparative genomics reveals a novel genetic organization of the sad cluster in the sulfonamide-degrader 'Candidatus Leucobacter sulfamidivorax' strain GP.BMC genomics · 2019Article
- Biodegradation of sulfamethoxazole by a bacterial consortium of Achromobacter denitrificans PR1 and Leucobacter sp. GP.Applied microbiology and biotechnology · 2018Article
- Isolation of the (+)-Pinoresinol-Mineralizing Pseudomonas sp. Strain SG-MS2 and Elucidation of Its Catabolic Pathway.Applied and environmental microbiology · 2018Article
- Gene cloning system for sulfonamide-mineralizing Microbacterium sp. strain BR1.Journal of applied genetics · 2018Article
- FMNHScientific reports · 2017Article
- Dye-sensitized TiOEnvironmental science and pollution research international · 2017Article
- Evaluation of Sulfadiazine Degradation in Three Newly Isolated Pure Bacterial Cultures.PloS one · 2016Article
Corrections and comments
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Authors and funding
12 authors at 3 institutions in 4 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
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.
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