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Sulfate radical-based oxidation of the antibiotics sulfamethoxazole, sulfisoxazole, sulfathiazole, and sulfamethizole: The role of five-membered heterocyclic rings.
Sci Total Environ. 2019 Nov 20; 692:201-208.ST

Abstract

The widespread occurrence of sulfonamides (SAs) in natural waters, wastewater, soil and sediment has raised increasing concerns about their potential risks to human health and ecological systems. Sulfate radical (SO4-)-based advanced oxidation processes (SR-AOPs) have become promising technologies to remove such contaminants in the environment. The present study systematically investigated the degradation of four selected SAs with different five-membered heterocyclic rings, namely, sulfamethoxazole (SMX), sulfisoxazole (SIX), sulfathiazole (STZ), and sulfamethizole (SMT), by thermo-activated persulfate (PS) process, and the role of heterocyclic rings was assessed particularly. The results revealed that all the selected SAs could be degraded efficiently by thermo-activated PS process and their decay rates were appreciably increased with increasing temperature. For instance, degradation rates of STZ increased from 0.3 × 10-3 to 19.5 × 10-3 min-1 as the temperature was increased from 30 to 60 °C. Under the same experimental conditions, the degradation rates of SAs followed the order of SIX > SMX ≈ STZ > SMT, which was in accordance with decay rates of their R-NH2 moieties. Kinetic results indicated that five-membered heterocyclic rings could serve as reactive moieties toward SO4- attack, which were confirmed by frontier electron density (FED) calculations. Based on the transformation products identified by high-resolution mass spectrometry (HR-MS), five different oxidation pathways, including hydroxylation, aniline moiety oxidation, dimerization, sulfonamide bond cleavage, and heterocyclic ring oxidation/cleavage were proposed. Moreover, the degradation efficiency in real surface water (RSW) was found to be slightly slower than that in artificial surface water (ASW), suggesting that SR-AOPs could be an efficient approach for remediation of soil and water contaminated by these SAs.

Authors+Show Affiliations

State Environmental Protection Key Lab of Environmental Risk Assessment and Control on Chemical Processes, School of Resources & Environmental Engineering, East China University of Science and Technology, Shanghai 200237, China; Shanghai Institute of Pollution Control and Ecological Security, Shanghai 200092, China. Electronic address: zhoulei@ecust.edu.cn.State Environmental Protection Key Lab of Environmental Risk Assessment and Control on Chemical Processes, School of Resources & Environmental Engineering, East China University of Science and Technology, Shanghai 200237, China.College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing 210095, China. Electronic address: yuefeiji@njau.edu.cn.School of Chemistry, Biology and Materials Engineering, Suzhou University of Science and Technology, Suzhou 215009, China. Electronic address: jwei@mail.usts.edu.cn.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31344571

Citation

Zhou, Lei, et al. "Sulfate Radical-based Oxidation of the Antibiotics Sulfamethoxazole, Sulfisoxazole, Sulfathiazole, and Sulfamethizole: the Role of Five-membered Heterocyclic Rings." The Science of the Total Environment, vol. 692, 2019, pp. 201-208.
Zhou L, Yang X, Ji Y, et al. Sulfate radical-based oxidation of the antibiotics sulfamethoxazole, sulfisoxazole, sulfathiazole, and sulfamethizole: The role of five-membered heterocyclic rings. Sci Total Environ. 2019;692:201-208.
Zhou, L., Yang, X., Ji, Y., & Wei, J. (2019). Sulfate radical-based oxidation of the antibiotics sulfamethoxazole, sulfisoxazole, sulfathiazole, and sulfamethizole: The role of five-membered heterocyclic rings. The Science of the Total Environment, 692, 201-208. https://doi.org/10.1016/j.scitotenv.2019.07.259
Zhou L, et al. Sulfate Radical-based Oxidation of the Antibiotics Sulfamethoxazole, Sulfisoxazole, Sulfathiazole, and Sulfamethizole: the Role of Five-membered Heterocyclic Rings. Sci Total Environ. 2019 Nov 20;692:201-208. PubMed PMID: 31344571.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Sulfate radical-based oxidation of the antibiotics sulfamethoxazole, sulfisoxazole, sulfathiazole, and sulfamethizole: The role of five-membered heterocyclic rings. AU - Zhou,Lei, AU - Yang,Xuerui, AU - Ji,Yuefei, AU - Wei,Jie, Y1 - 2019/07/17/ PY - 2019/04/16/received PY - 2019/07/03/revised PY - 2019/07/16/accepted PY - 2019/7/26/pubmed PY - 2020/1/14/medline PY - 2019/7/26/entrez KW - Heterocyclic rings KW - Persulfate KW - Sulfamethoxazole KW - Sulfate radical KW - Sulfonamide antibiotics KW - Transformation SP - 201 EP - 208 JF - The Science of the total environment JO - Sci. Total Environ. VL - 692 N2 - The widespread occurrence of sulfonamides (SAs) in natural waters, wastewater, soil and sediment has raised increasing concerns about their potential risks to human health and ecological systems. Sulfate radical (SO4-)-based advanced oxidation processes (SR-AOPs) have become promising technologies to remove such contaminants in the environment. The present study systematically investigated the degradation of four selected SAs with different five-membered heterocyclic rings, namely, sulfamethoxazole (SMX), sulfisoxazole (SIX), sulfathiazole (STZ), and sulfamethizole (SMT), by thermo-activated persulfate (PS) process, and the role of heterocyclic rings was assessed particularly. The results revealed that all the selected SAs could be degraded efficiently by thermo-activated PS process and their decay rates were appreciably increased with increasing temperature. For instance, degradation rates of STZ increased from 0.3 × 10-3 to 19.5 × 10-3 min-1 as the temperature was increased from 30 to 60 °C. Under the same experimental conditions, the degradation rates of SAs followed the order of SIX > SMX ≈ STZ > SMT, which was in accordance with decay rates of their R-NH2 moieties. Kinetic results indicated that five-membered heterocyclic rings could serve as reactive moieties toward SO4- attack, which were confirmed by frontier electron density (FED) calculations. Based on the transformation products identified by high-resolution mass spectrometry (HR-MS), five different oxidation pathways, including hydroxylation, aniline moiety oxidation, dimerization, sulfonamide bond cleavage, and heterocyclic ring oxidation/cleavage were proposed. Moreover, the degradation efficiency in real surface water (RSW) was found to be slightly slower than that in artificial surface water (ASW), suggesting that SR-AOPs could be an efficient approach for remediation of soil and water contaminated by these SAs. SN - 1879-1026 UR - https://www.unboundmedicine.com/medline/citation/31344571/Sulfate_radical_based_oxidation_of_the_antibiotics_sulfamethoxazole_sulfisoxazole_sulfathiazole_and_sulfamethizole:_The_role_of_five_membered_heterocyclic_rings_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0048-9697(19)33373-X DB - PRIME DP - Unbound Medicine ER -