Synthesis of typical sulfonamide antibiotics with [14C]- and [13C]-labeling on the phenyl ring for use in environmental studies
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Publication date
08.03.2022
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01A - Journal article
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Environmental Sciences Europe
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Volume
34
Issue / Number
1
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Springer
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Abstract
Background
Due to their widespread use, sulfonamide antibiotics (SAs) have become ubiquitous environmental contaminants and thus a cause of public concern. However, a complete understanding of the behavior of these pollutants in complex environmental systems has been hampered by the unavailability and high cost of isotopically labeled SAs.
Results
Using commercially available uniformly [14C]- and [13C]-labeled aniline as starting materials, we synthesized [phenyl-ring-14C]- and [phenyl-ring-13C]-labeled sulfamethoxazole (SMX), sulfamonomethoxine (SMM), and sulfadiazine (SDZ) in four-step (via the condensation of labeled N-acetylsulfanilyl chloride and aminoheterocycles) or five-step (via the condensation of labeled N-acetylsulfonamide and chloroheterocycles) reactions, with good yields (5.0–22.5% and 28.1–54.1% for [14C]- and [13C]-labeled SAs, respectively) and high purities (> 98.0%).
Conclusion
The synthesis of [14C]-labeled SAs in milligram amounts enables the preparation of labeled SAs with high specific radioactivity. The efficient and feasible methods described herein can be applied to the production of a variety of [14C]- or [13C]-labeled SAs for studies on their environmental behavior, including the fate, transformation, and bioaccumulation of these antibiotics in soils and aqueous systems.
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2190-4707
2190-4715
2190-4715
Language
English
Created during FHNW affiliation
Yes
Strategic action fields FHNW
Publication status
Published
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Peer review of the complete publication
Open access category
Gold
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Citation
Wu, X., Yao, Y., Wang, L., Zhou, D., Sun, F., Chen, J., Ji, R., & Corvini, P. (2022). Synthesis of typical sulfonamide antibiotics with [14C]- and [13C]-labeling on the phenyl ring for use in environmental studies. Environmental Sciences Europe, 34(1). https://doi.org/10.1186/s12302-022-00598-z