Synthesis of typical sulfonamide antibiotics with [14C]- and [13C]-labeling on the phenyl ring for use in environmental studies

Wu, Xuan; Yao, Yao; Wang, Lianhong; Zhou, Dewang; Sun, Feifei; Chen, Jianqiu; Corvini, Philippe F.-X.; Ji, Rong

doi:10.1186/s12302-022-00598-z

Cited by 5 publications

(2 citation statements)

References 41 publications

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“…[Uniformly phenyl-ring- l4 C]-labeled SMX ( 14 C-SMX, 355 MBq/mmol, 98% radiochemical purity) and N -acetylated SMX [ N -(4-( N -(5-methylisoxazol-3-yl)sulfamoyl)phenyl)acetamide, 95% purity] (TP5, see Section ) were synthesized according to our previous report . Four identified TPs of SMX, i.e., N -lactylated SMX [2-hydroxy- N -(4-( N -(5-methylisoxazol-3-yl)sulfamoyl)phenyl)propanamide] (TP3), hydroxyl-substituted SMX [4-hydroxy- N -(5-methylisoxazol-3-yl)benzenesulfonamide] (TP4), N 4 -chloro-SMX [4-(chloroamino)- N -(5-methylisoxazol-3-yl)benzenesulfonamide] (silylation byproduct of SMX), and deaminated SMX [ N -(5-methylisoxazol-3-yl)benzenesulfonamide] (TP6), were synthesized as described in Texts S1–S4, respectively.…”

Section: Methodsmentioning

confidence: 99%

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Maize (Zea mays L.) Plants Alter the Fate and Accumulate Nonextractable Residues of Sulfamethoxazole in Farmland Soil

Wu,

Sun,

Cao

et al. 2024

Environ. Sci. Technol.

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The fate of sulfonamide antibiotics in farmlands is crucial for food and ecological safety, yet it remains unclear. We used [phenyl-U-14 C]-labeled sulfamethoxazole ( 14 C-SMX) to quantitatively investigate the fate of SMX in a soil−maize system for 60 days, based on a six-pool fate model. Formation of nonextractable residues (NERs) was the predominant fate for SMX in unplanted soil, accompanied by minor mineralization. Notably, maize plants significantly increased SMX dissipation (kinetic constant k d = 0.30 day −1 vs 0.17 day −1 ), while substantially reducing the NER formation (92% vs 58% of initially applied SMX) and accumulating SMX (40%, mostly bound to roots). Significant NERs (maximal 29−42%) were formed via physicochemical entrapment (determined using silylation), which could partially be released and taken up by maize plants. The NERs consisted of a considerable amount of SMX formed via entrapment (1−8%) and alkali-hydrolyzable covalent bonds (2−12%, possibly amide linkage). Six and 10 transformation products were quantified in soil extracts and NERs, respectively, including products of hydroxyl substitution, deamination, and N-acylation, among which Nlactylated SMX was found for the first time. Our findings reveal the composition and instability of SMX-derived NERs in the soil− plant system and underscore the need to study the long-term impacts of reversible NERs.

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Section: Methodsmentioning

confidence: 99%

Section: Chemicalsmentioning

confidence: 99%

Maize (Zea mays L.) Plants Alter the Fate and Accumulate Nonextractable Residues of Sulfamethoxazole in Farmland Soil

Wu,

Sun,

Cao

et al. 2024

Environ. Sci. Technol.

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Biochar nanoparticles-mediated transport of organic contaminants in porous media: dependency on contaminant properties and effects of biochar aging

Peng

et al. 2023

Carbon Res.

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Land application of biochar has been recommended as an effective soil amendment measure. Nonetheless, the applied biochar can accumulate co-existing contaminants. Meanwhile, nanoparticles formed due to biochar disintegration may facilitate contaminant transport in vadose zone and groundwater, posing a potential risk to the subsurface environment. Here, we show that the presence of pinewood- and rice straw-derived biochar nanoparticles (BCNPs) at parts per million level (~ 20 mg/L) can result in significant mobilization of hydrophobic, nonpolar contaminants (naphthalene and pyrene) and positively charged polar contaminants (trimethoprim and ciprofloxacin) in saturated sandy soil, but slightly inhibits the transport of negatively charged or neutral hydrophilic compounds (sulfamethoxazole and bisphenol A). With supplemental adsorption and desorption experiments we show that the ability of BCNPs in mediating contaminant transport (either enhancing or inhibiting) relies primarily on the extent of irreversible binding of a contaminant to the BCNPs. Sulfide reduction and leaching of organic carbon, two relatively mild (in terms of modification of physicochemical properties, e.g., surface O/C ratio) but widely occurring aging processes, facilitate co-transport of pyrene and bisphenol A with the BCNPs. However, this is mainly the result of increased mobility of the BCNPs (i.e., the carrier), rather than enhanced interactions between the BCNPs and the contaminants being carried. The findings underline the significant effects of BCNPs on the fate and transport of environmental contaminants, and further highlight the important role of aging in affecting environmental behaviors and effects of biochar materials. Graphical Abstract

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A new strategy for immobilization of copper on the Fe3O4@EDTA nanocomposite and its efficient catalytic applications in reduction and one-pot reductive acetylation of nitroarenes and also N-acetylation of arylamines

Mavaddatiyan,

Zeynizadeh

2024

Heliyon

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Synthesis of typical sulfonamide antibiotics with [14C]- and [13C]-labeling on the phenyl ring for use in environmental studies

Cited by 5 publications

References 41 publications

Maize (Zea mays L.) Plants Alter the Fate and Accumulate Nonextractable Residues of Sulfamethoxazole in Farmland Soil

Maize (Zea mays L.) Plants Alter the Fate and Accumulate Nonextractable Residues of Sulfamethoxazole in Farmland Soil

Biochar nanoparticles-mediated transport of organic contaminants in porous media: dependency on contaminant properties and effects of biochar aging

A new strategy for immobilization of copper on the Fe3O4@EDTA nanocomposite and its efficient catalytic applications in reduction and one-pot reductive acetylation of nitroarenes and also N-acetylation of arylamines

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