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Comparison of chemical and biological degradation of sulfonamides: Solving the mystery of sulfonamide transformation.
J Hazard Mater. 2022 02 15; 424(Pt D):127661.JH

Abstract

Sulfonamides (SAs) are widespread in aquatic environments and pose serious environmental risks. The removal efficiencies and degradation mechanisms of SAs in both chemical and biological degradation systems were comprehensively reviewed. Density functional theory (DFT) was utilized to decipher the reaction types and reactive sites of both degradation mechanisms at the electron level. In chemical degradation, the rate of the reactive oxidants to degrade SAs follows the order SO4•- ≈ •OH > O3 > 1O2 > ClO2 ≈ Fe(VI) ≈ HOCl > peroxymonosulfate. pH affects the oxidation-reduction potentials of oxidants, the reactivity of SAs, and the intermolecular force between oxidants and SAs, thereby affecting the chemical degradation efficiencies and mechanisms. In biological degradation, oxidoreductase produced by bacteria, fungi, algae, and plants can degrade SAs. The catalytic activity of the enzyme is affected by the enzyme system, reaction conditions, and type of SAs. Despite the different reaction modes and removal efficiencies of SAs in chemical degradation and biological degradation, the transformation pathways and products show commonalities. Modification of the amino (N1H2-) moiety and destruction of sulfonamide bridge (-SO2-N11H-) moiety are the main pathways for both chemical and biological degradation of SAs. Most oxidants or enzymes can react with the N1H2- moiety. Reactions of the -SO2-N11H- moiety are mainly initiated by the cleavage of S-N bonds for five-membered heterocyclic ring-substituted SAs, and by SO2 extrusion for six-membered heterocyclic ring-substituted SAs. Chlorine substitution and coupling on the N1H2- moiety, hydroxylation of the benzene moiety, oxidation of methyl, and isomerization of the R substituents are the transformation pathways unique to chemical degradation. Formylation/acetylation, glycosylation, pterin conjugation, and deamination of the N1H2- moiety are the transformation pathways unique to biological degradation. DFT studies revealed the same reaction types and the same reactive sites of SAs in chemical and biological degradation. Electrophiles are mostly prone to attack the N1 atom on the amino moiety of neutral SAs and the N11 atom on the sulfonamide bridge moiety of anionic SAs, leading to nitration or electrophilic substitution of the amino moiety and the cleavage of S-N bonds or SO2 extrusion of the sulfonamide bridge moiety. Reactions on the -SO2-N11H- moiety eliminate antibacterial activity in the SA degradation process. This review elucidated SA transformation by comparing the chemical and biological degradation of SAs. This could provide theoretical guidance for the development of more efficient and economical treatment technologies for SAs.

Authors+Show Affiliations

Guangdong Provincial Engineering Research Center for Urban Water Recycling and Environmental Safety, Tsinghua Shenzhen International Graduate School, Tsinghua University, Shenzhen 518055, China; School of Environment, Tsinghua University, Beijing 100084, China.Guangdong Provincial Engineering Research Center for Urban Water Recycling and Environmental Safety, Tsinghua Shenzhen International Graduate School, Tsinghua University, Shenzhen 518055, China; Shenzhen Environmental Science and New Energy Laboratory, Tsinghua-Berkeley Shenzhen Institute, Tsinghua University, Shenzhen 518055, China.Guangdong Provincial Engineering Research Center for Urban Water Recycling and Environmental Safety, Tsinghua Shenzhen International Graduate School, Tsinghua University, Shenzhen 518055, China; School of Environment, Tsinghua University, Beijing 100084, China.Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong 518055, China.Guangdong Provincial Engineering Research Center for Urban Water Recycling and Environmental Safety, Tsinghua Shenzhen International Graduate School, Tsinghua University, Shenzhen 518055, China.Guangdong Provincial Engineering Research Center for Urban Water Recycling and Environmental Safety, Tsinghua Shenzhen International Graduate School, Tsinghua University, Shenzhen 518055, China. Electronic address: bingli@sz.tsinghua.edu.cn.

Pub Type(s)

Journal Article
Review
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

34763922

Citation

Hu, Jiahui, et al. "Comparison of Chemical and Biological Degradation of Sulfonamides: Solving the Mystery of Sulfonamide Transformation." Journal of Hazardous Materials, vol. 424, no. Pt D, 2022, p. 127661.
Hu J, Li X, Liu F, et al. Comparison of chemical and biological degradation of sulfonamides: Solving the mystery of sulfonamide transformation. J Hazard Mater. 2022;424(Pt D):127661.
Hu, J., Li, X., Liu, F., Fu, W., Lin, L., & Li, B. (2022). Comparison of chemical and biological degradation of sulfonamides: Solving the mystery of sulfonamide transformation. Journal of Hazardous Materials, 424(Pt D), 127661. https://doi.org/10.1016/j.jhazmat.2021.127661
Hu J, et al. Comparison of Chemical and Biological Degradation of Sulfonamides: Solving the Mystery of Sulfonamide Transformation. J Hazard Mater. 2022 02 15;424(Pt D):127661. PubMed PMID: 34763922.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Comparison of chemical and biological degradation of sulfonamides: Solving the mystery of sulfonamide transformation. AU - Hu,Jiahui, AU - Li,Xiaoyan, AU - Liu,Feifei, AU - Fu,Wenjie, AU - Lin,Lin, AU - Li,Bing, Y1 - 2021/10/30/ PY - 2021/08/11/received PY - 2021/10/13/revised PY - 2021/10/28/accepted PY - 2021/11/13/pubmed PY - 2021/11/13/medline PY - 2021/11/12/entrez KW - Antibiotics removal KW - Density function theory KW - Electrophilic reaction KW - Functional enzyme KW - Reactive oxidants KW - SO(2) extrusion SP - 127661 EP - 127661 JF - Journal of hazardous materials JO - J Hazard Mater VL - 424 IS - Pt D N2 - Sulfonamides (SAs) are widespread in aquatic environments and pose serious environmental risks. The removal efficiencies and degradation mechanisms of SAs in both chemical and biological degradation systems were comprehensively reviewed. Density functional theory (DFT) was utilized to decipher the reaction types and reactive sites of both degradation mechanisms at the electron level. In chemical degradation, the rate of the reactive oxidants to degrade SAs follows the order SO4•- ≈ •OH > O3 > 1O2 > ClO2 ≈ Fe(VI) ≈ HOCl > peroxymonosulfate. pH affects the oxidation-reduction potentials of oxidants, the reactivity of SAs, and the intermolecular force between oxidants and SAs, thereby affecting the chemical degradation efficiencies and mechanisms. In biological degradation, oxidoreductase produced by bacteria, fungi, algae, and plants can degrade SAs. The catalytic activity of the enzyme is affected by the enzyme system, reaction conditions, and type of SAs. Despite the different reaction modes and removal efficiencies of SAs in chemical degradation and biological degradation, the transformation pathways and products show commonalities. Modification of the amino (N1H2-) moiety and destruction of sulfonamide bridge (-SO2-N11H-) moiety are the main pathways for both chemical and biological degradation of SAs. Most oxidants or enzymes can react with the N1H2- moiety. Reactions of the -SO2-N11H- moiety are mainly initiated by the cleavage of S-N bonds for five-membered heterocyclic ring-substituted SAs, and by SO2 extrusion for six-membered heterocyclic ring-substituted SAs. Chlorine substitution and coupling on the N1H2- moiety, hydroxylation of the benzene moiety, oxidation of methyl, and isomerization of the R substituents are the transformation pathways unique to chemical degradation. Formylation/acetylation, glycosylation, pterin conjugation, and deamination of the N1H2- moiety are the transformation pathways unique to biological degradation. DFT studies revealed the same reaction types and the same reactive sites of SAs in chemical and biological degradation. Electrophiles are mostly prone to attack the N1 atom on the amino moiety of neutral SAs and the N11 atom on the sulfonamide bridge moiety of anionic SAs, leading to nitration or electrophilic substitution of the amino moiety and the cleavage of S-N bonds or SO2 extrusion of the sulfonamide bridge moiety. Reactions on the -SO2-N11H- moiety eliminate antibacterial activity in the SA degradation process. This review elucidated SA transformation by comparing the chemical and biological degradation of SAs. This could provide theoretical guidance for the development of more efficient and economical treatment technologies for SAs. SN - 1873-3336 UR - https://www.unboundmedicine.com/medline/citation/34763922/Comparison_of_chemical_and_biological_degradation_of_sulfonamides:_Solving_the_mystery_of_sulfonamide_transformation_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0304-3894(21)02629-7 DB - PRIME DP - Unbound Medicine ER -
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