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Sulfate radical-based oxidation of fluoroquinolone antibiotics: Kinetics, mechanisms and effects of natural water matrices.
Water Res. 2016 Dec 01; 106:507-517.WR

Abstract

Widespread occurrence of fluoroquinolone antibiotics (FQs) in surface water, groundwater, soil and sediment has been reported and their remediation is essentially needed. Sulfate radical (SO4-) based advanced oxidation processes (SR-AOPs) are promising technologies for soil and groundwater remediation. In this study, the degradation kinetics, mechanisms, and effects of natural water matrices on heat-activated persulfate (PS) oxidation of FQs were systematically investigated. Experimental results clearly demonstrated that 92% of CIP was removed within 180 min (pH = 7, 60 °C). Higher temperature and lower pH facilitated the degradation of ciprofloxacin (CIP). The piperazine moiety of CIP was identified as the reactive site for SO4- attack by comparison with substructural analogs, flumequine (FLU) and 1-(2-fluorophenyl) piperazine (FPP). A comparison of the degradation of CIP, norfloxacin (NOR), enrofloxacin (ENR) and ofloxacin (OFL) confirmed that the presence of cyclopropane ring also influence the degradation of FQs. Water matrix significantly influenced the degradation of CIP and ENR, and the degradation rate followed the order of Milli-Q water (pH = 7) > groundwater > artificial seawater > artificial surface water > lake water. Degradation products of CIP in different water matrix were enriched by solid phase extraction (SPE) and then analyzed by liquid chromatography-electrospray ionization-triple quadrupole mass spectrometry (LC-ESI-MS/MS). Detailed transformation pathways of CIP were proposed and were compared with respect to different water matrices. Four transformation pathways including stepwise piperazine ring oxidation, OH/F substitution, hydroxylation, and cyclopropane ring cleavage were proposed for CIP degradation. Results clearly show that the water matrix influenced the degradation of FQs appreciably, a phenomenon that should be taken into consideration when applying SR-AOPs for remediation of soil and groundwater contaminated by FQs.

Authors+Show Affiliations

College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing 210095, China.College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing 210095, China.College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing 210095, China.College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing 210095, China.College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing 210095, China. Electronic address: ctm@njau.edu.cn.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

27770727

Citation

Jiang, Canlan, et al. "Sulfate Radical-based Oxidation of Fluoroquinolone Antibiotics: Kinetics, Mechanisms and Effects of Natural Water Matrices." Water Research, vol. 106, 2016, pp. 507-517.
Jiang C, Ji Y, Shi Y, et al. Sulfate radical-based oxidation of fluoroquinolone antibiotics: Kinetics, mechanisms and effects of natural water matrices. Water Res. 2016;106:507-517.
Jiang, C., Ji, Y., Shi, Y., Chen, J., & Cai, T. (2016). Sulfate radical-based oxidation of fluoroquinolone antibiotics: Kinetics, mechanisms and effects of natural water matrices. Water Research, 106, 507-517. https://doi.org/10.1016/j.watres.2016.10.025
Jiang C, et al. Sulfate Radical-based Oxidation of Fluoroquinolone Antibiotics: Kinetics, Mechanisms and Effects of Natural Water Matrices. Water Res. 2016 Dec 1;106:507-517. PubMed PMID: 27770727.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Sulfate radical-based oxidation of fluoroquinolone antibiotics: Kinetics, mechanisms and effects of natural water matrices. AU - Jiang,Canlan, AU - Ji,Yuefei, AU - Shi,Yuanyuan, AU - Chen,Jifei, AU - Cai,Tianming, Y1 - 2016/10/12/ PY - 2016/07/12/received PY - 2016/10/07/revised PY - 2016/10/09/accepted PY - 2016/11/7/entrez PY - 2016/10/23/pubmed PY - 2017/5/5/medline KW - Ciprofloxacin KW - Fluoroquinolone antibiotics KW - Sulfate radical KW - Transformation mechanisms KW - Water matrix SP - 507 EP - 517 JF - Water research JO - Water Res. VL - 106 N2 - Widespread occurrence of fluoroquinolone antibiotics (FQs) in surface water, groundwater, soil and sediment has been reported and their remediation is essentially needed. Sulfate radical (SO4-) based advanced oxidation processes (SR-AOPs) are promising technologies for soil and groundwater remediation. In this study, the degradation kinetics, mechanisms, and effects of natural water matrices on heat-activated persulfate (PS) oxidation of FQs were systematically investigated. Experimental results clearly demonstrated that 92% of CIP was removed within 180 min (pH = 7, 60 °C). Higher temperature and lower pH facilitated the degradation of ciprofloxacin (CIP). The piperazine moiety of CIP was identified as the reactive site for SO4- attack by comparison with substructural analogs, flumequine (FLU) and 1-(2-fluorophenyl) piperazine (FPP). A comparison of the degradation of CIP, norfloxacin (NOR), enrofloxacin (ENR) and ofloxacin (OFL) confirmed that the presence of cyclopropane ring also influence the degradation of FQs. Water matrix significantly influenced the degradation of CIP and ENR, and the degradation rate followed the order of Milli-Q water (pH = 7) > groundwater > artificial seawater > artificial surface water > lake water. Degradation products of CIP in different water matrix were enriched by solid phase extraction (SPE) and then analyzed by liquid chromatography-electrospray ionization-triple quadrupole mass spectrometry (LC-ESI-MS/MS). Detailed transformation pathways of CIP were proposed and were compared with respect to different water matrices. Four transformation pathways including stepwise piperazine ring oxidation, OH/F substitution, hydroxylation, and cyclopropane ring cleavage were proposed for CIP degradation. Results clearly show that the water matrix influenced the degradation of FQs appreciably, a phenomenon that should be taken into consideration when applying SR-AOPs for remediation of soil and groundwater contaminated by FQs. SN - 1879-2448 UR - https://www.unboundmedicine.com/medline/citation/27770727/Sulfate_radical_based_oxidation_of_fluoroquinolone_antibiotics:_Kinetics_mechanisms_and_effects_of_natural_water_matrices_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0043-1354(16)30777-1 DB - PRIME DP - Unbound Medicine ER -