Oxidation of fluoroquinolone antibiotics by peroxymonosulfate without activation: Kinetics, products, and antibacterial deactivation
While fluoroquinolone (FQ) antibiotics are susceptible to degradation by sulfate and/or hydroxyl radicals formed in peroxymonosulfate (PMS) based advanced oxidation processes, here we report that unactivated PMS itself exhibits a specific high reactivity toward FQs for the first time. Reaction kinet...
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Published in | Water research (Oxford) Vol. 145; pp. 210 - 219 |
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Main Authors | , , , , , , , , |
Format | Journal Article |
Language | English |
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England
Elsevier Ltd
15.11.2018
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Abstract | While fluoroquinolone (FQ) antibiotics are susceptible to degradation by sulfate and/or hydroxyl radicals formed in peroxymonosulfate (PMS) based advanced oxidation processes, here we report that unactivated PMS itself exhibits a specific high reactivity toward FQs for the first time. Reaction kinetics of PMS with two model FQs, ciprofloxacin (CF) and enrofloxacin (EF), showed a strong pH dependency with apparent second-order rate constants of 0.10–13.05 M−1s−1 for CF and 0.51–33.17 M−1s−1 for EF at pH 5–10. This pH dependency was well described by species-specific parallel reactions. On the basis of reaction kinetics and structure–activity assessment, the tertiary and secondary aliphatic N4 amines on the FQs’ piperazine ring were proposed to be the main reaction sites. High performance liquid chromatography/electrospray ionization tandem mass analysis showed the formation of hydroxylated, N-oxide, and dealkylated products. Bacterial growth inhibition bioassays using Escherichia coli showed that oxidation products of FQs by PMS retained negligible antibacterial potency in comparison to parent FQs. Kinetic modeling using the rate constants estimated from pure water well predicted the oxidation kinetics of low levels of CF and EF by PMS in surface water. The degradation efficiency of FQs by PMS in surface water was slightly lower than that by ozone, comparable to that by ferrate, and much higher than that by permanganate. These results suggest that PMS is a promising oxidant for the treatment of FQs in water.
[Display omitted]
•Direct oxidation of FQs by PMS without activation showed strong pH dependency.•Aliphatic N4 amines on the FQs' piperazine ring were the main reaction sites.•Transformation of FQs yielded hydroxylated, N-oxide, and dealkylated products.•Oxidation products had a much lower antibacterial activity than parent FQs.•FQs were efficiently degraded by PMS in natural water. |
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AbstractList | While fluoroquinolone (FQ) antibiotics are susceptible to degradation by sulfate and/or hydroxyl radicals formed in peroxymonosulfate (PMS) based advanced oxidation processes, here we report that unactivated PMS itself exhibits a specific high reactivity toward FQs for the first time. Reaction kinetics of PMS with two model FQs, ciprofloxacin (CF) and enrofloxacin (EF), showed a strong pH dependency with apparent second-order rate constants of 0.10-13.05 M-1s-1 for CF and 0.51-33.17 M-1s-1 for EF at pH 5-10. This pH dependency was well described by species-specific parallel reactions. On the basis of reaction kinetics and structure-activity assessment, the tertiary and secondary aliphatic N4 amines on the FQs' piperazine ring were proposed to be the main reaction sites. High performance liquid chromatography/electrospray ionization tandem mass analysis showed the formation of hydroxylated, N-oxide, and dealkylated products. Bacterial growth inhibition bioassays using Escherichia coli showed that oxidation products of FQs by PMS retained negligible antibacterial potency in comparison to parent FQs. Kinetic modeling using the rate constants estimated from pure water well predicted the oxidation kinetics of low levels of CF and EF by PMS in surface water. The degradation efficiency of FQs by PMS in surface water was slightly lower than that by ozone, comparable to that by ferrate, and much higher than that by permanganate. These results suggest that PMS is a promising oxidant for the treatment of FQs in water. While fluoroquinolone (FQ) antibiotics are susceptible to degradation by sulfate and/or hydroxyl radicals formed in peroxymonosulfate (PMS) based advanced oxidation processes, here we report that unactivated PMS itself exhibits a specific high reactivity toward FQs for the first time. Reaction kinetics of PMS with two model FQs, ciprofloxacin (CF) and enrofloxacin (EF), showed a strong pH dependency with apparent second-order rate constants of 0.10-13.05 M s for CF and 0.51-33.17 M s for EF at pH 5-10. This pH dependency was well described by species-specific parallel reactions. On the basis of reaction kinetics and structure-activity assessment, the tertiary and secondary aliphatic N4 amines on the FQs' piperazine ring were proposed to be the main reaction sites. High performance liquid chromatography/electrospray ionization tandem mass analysis showed the formation of hydroxylated, N-oxide, and dealkylated products. Bacterial growth inhibition bioassays using Escherichia coli showed that oxidation products of FQs by PMS retained negligible antibacterial potency in comparison to parent FQs. Kinetic modeling using the rate constants estimated from pure water well predicted the oxidation kinetics of low levels of CF and EF by PMS in surface water. The degradation efficiency of FQs by PMS in surface water was slightly lower than that by ozone, comparable to that by ferrate, and much higher than that by permanganate. These results suggest that PMS is a promising oxidant for the treatment of FQs in water. While fluoroquinolone (FQ) antibiotics are susceptible to degradation by sulfate and/or hydroxyl radicals formed in peroxymonosulfate (PMS) based advanced oxidation processes, here we report that unactivated PMS itself exhibits a specific high reactivity toward FQs for the first time. Reaction kinetics of PMS with two model FQs, ciprofloxacin (CF) and enrofloxacin (EF), showed a strong pH dependency with apparent second-order rate constants of 0.10–13.05 M−1s−1 for CF and 0.51–33.17 M−1s−1 for EF at pH 5–10. This pH dependency was well described by species-specific parallel reactions. On the basis of reaction kinetics and structure–activity assessment, the tertiary and secondary aliphatic N4 amines on the FQs’ piperazine ring were proposed to be the main reaction sites. High performance liquid chromatography/electrospray ionization tandem mass analysis showed the formation of hydroxylated, N-oxide, and dealkylated products. Bacterial growth inhibition bioassays using Escherichia coli showed that oxidation products of FQs by PMS retained negligible antibacterial potency in comparison to parent FQs. Kinetic modeling using the rate constants estimated from pure water well predicted the oxidation kinetics of low levels of CF and EF by PMS in surface water. The degradation efficiency of FQs by PMS in surface water was slightly lower than that by ozone, comparable to that by ferrate, and much higher than that by permanganate. These results suggest that PMS is a promising oxidant for the treatment of FQs in water. [Display omitted] •Direct oxidation of FQs by PMS without activation showed strong pH dependency.•Aliphatic N4 amines on the FQs' piperazine ring were the main reaction sites.•Transformation of FQs yielded hydroxylated, N-oxide, and dealkylated products.•Oxidation products had a much lower antibacterial activity than parent FQs.•FQs were efficiently degraded by PMS in natural water. |
Author | Gao, Yuan Guo, Qin Zhou, Yang Jiang, Jin Ma, Jun Duan, Jiebin Yang, Yue Pang, Su-Yan Yang, Yi |
Author_xml | – sequence: 1 givenname: Yang surname: Zhou fullname: Zhou, Yang organization: State Key Laboratory of Urban Water Resource and Environment, School of Environment, Harbin Institute of Technology, Harbin, 150090, China – sequence: 2 givenname: Yuan surname: Gao fullname: Gao, Yuan organization: State Key Laboratory of Urban Water Resource and Environment, School of Environment, Harbin Institute of Technology, Harbin, 150090, China – sequence: 3 givenname: Su-Yan surname: Pang fullname: Pang, Su-Yan email: psyhit@126.com organization: School of Municipal and Environmental Engineering, Jilin Jianzhu University, Changchun, 130118, China – sequence: 4 givenname: Jin surname: Jiang fullname: Jiang, Jin organization: State Key Laboratory of Urban Water Resource and Environment, School of Environment, Harbin Institute of Technology, Harbin, 150090, China – sequence: 5 givenname: Yi surname: Yang fullname: Yang, Yi organization: State Key Laboratory of Urban Water Resource and Environment, School of Environment, Harbin Institute of Technology, Harbin, 150090, China – sequence: 6 givenname: Jun surname: Ma fullname: Ma, Jun organization: State Key Laboratory of Urban Water Resource and Environment, School of Environment, Harbin Institute of Technology, Harbin, 150090, China – sequence: 7 givenname: Yue surname: Yang fullname: Yang, Yue organization: College of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin, 150040, China – sequence: 8 givenname: Jiebin surname: Duan fullname: Duan, Jiebin organization: College of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin, 150040, China – sequence: 9 givenname: Qin surname: Guo fullname: Guo, Qin organization: College of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin, 150040, China |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30142519$$D View this record in MEDLINE/PubMed |
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Keywords | Antibacterial deactivation Oxidation kinetics Peroxymonosulfate Fluoroquinolone antibiotics Oxidation products |
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SubjectTerms | Antibacterial deactivation Fluoroquinolone antibiotics Oxidation kinetics Oxidation products Peroxymonosulfate |
Title | Oxidation of fluoroquinolone antibiotics by peroxymonosulfate without activation: Kinetics, products, and antibacterial deactivation |
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