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Oxidation of ciprofloxacin and enrofloxacin by ferrate(VI): Products identification, and toxicity evaluation.
J Hazard Mater. 2016 Dec 15; 320:296-303.JH

Abstract

Ferrate(VI) (Fe(VI)) has been known to react with emerging organic contaminants containing electron-rich organic moieties, such as phenols, anilines, olefins, reduced sulfur and deprotonated amines. Oxidation of fluoroquinolone antibiotics, ciprofloxacin (CIP) and enrofloxacin (ENR), by Fe(VI) were investigated for their reaction products and toxicity changes as well as biodegradability of these products. Ten products were identified for both CIP and ENR reactions with Fe(VI) using a high-resolution accurate-mass Orbitrap mass analyzer. Structural changes to the CIP and ENR molecule included dealkylation, formation of alcohols and amides in piperazine ring and oxygen transfer to the double bond in quinolone structure. An enamine formation mechanism was tentatively proposed to facilitate the interpretation of CIP and ENR oxidation pathways. Toxicity evaluation using Microbial Assay for toxicity Risk Assessment (MARA) bioassay indicated that Fe(VI) oxidation products of CIP and ENR contributed negligible antibacterial potency and Fe(VI) oxidation treatment can remove the residual toxicity of CIP and ENR impacted source waters. The Fe(VI) oxidation treatment resulted in formation of relatively more biodegradable products (based on in silico assessment) than their corresponding parent compounds. The results showed that Fe(VI) has a good potential to degrade fluoroquinolone antibiotics and their antimicrobial potency in natural waters.

Authors+Show Affiliations

CSIRO Land and Water, Waite Campus, PMB 2, Glen Osmond, South Australia 5064, Australia. Electronic address: Bin.Yang@csiro.au.CSIRO Land and Water, Waite Campus, PMB 2, Glen Osmond, South Australia 5064, Australia.CSIRO Land and Water, Waite Campus, PMB 2, Glen Osmond, South Australia 5064, Australia.State Key Laboratory of Organic Geochemistry, Guangzhou Institute of Geochemistry, Chinese Academy of Sciences, Guangzhou 510640, China.CSIRO Land and Water, Waite Campus, PMB 2, Glen Osmond, South Australia 5064, Australia.CSIRO Land and Water, Waite Campus, PMB 2, Glen Osmond, South Australia 5064, Australia.CSIRO Land and Water, Waite Campus, PMB 2, Glen Osmond, South Australia 5064, Australia.

Pub Type(s)

Evaluation Study
Journal Article

Language

eng

PubMed ID

27565854

Citation

Yang, Bin, et al. "Oxidation of Ciprofloxacin and Enrofloxacin By ferrate(VI): Products Identification, and Toxicity Evaluation." Journal of Hazardous Materials, vol. 320, 2016, pp. 296-303.
Yang B, Kookana RS, Williams M, et al. Oxidation of ciprofloxacin and enrofloxacin by ferrate(VI): Products identification, and toxicity evaluation. J Hazard Mater. 2016;320:296-303.
Yang, B., Kookana, R. S., Williams, M., Ying, G. G., Du, J., Doan, H., & Kumar, A. (2016). Oxidation of ciprofloxacin and enrofloxacin by ferrate(VI): Products identification, and toxicity evaluation. Journal of Hazardous Materials, 320, 296-303. https://doi.org/10.1016/j.jhazmat.2016.08.040
Yang B, et al. Oxidation of Ciprofloxacin and Enrofloxacin By ferrate(VI): Products Identification, and Toxicity Evaluation. J Hazard Mater. 2016 Dec 15;320:296-303. PubMed PMID: 27565854.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Oxidation of ciprofloxacin and enrofloxacin by ferrate(VI): Products identification, and toxicity evaluation. AU - Yang,Bin, AU - Kookana,Rai S, AU - Williams,Mike, AU - Ying,Guang-Guo, AU - Du,Jun, AU - Doan,Hai, AU - Kumar,Anupama, Y1 - 2016/08/16/ PY - 2016/05/31/received PY - 2016/08/03/revised PY - 2016/08/15/accepted PY - 2016/8/28/pubmed PY - 2018/2/13/medline PY - 2016/8/28/entrez KW - Environmental toxicity KW - Ferrate(VI) KW - Fluoroquinolones KW - Oxidation KW - Transformation products SP - 296 EP - 303 JF - Journal of hazardous materials JO - J Hazard Mater VL - 320 N2 - Ferrate(VI) (Fe(VI)) has been known to react with emerging organic contaminants containing electron-rich organic moieties, such as phenols, anilines, olefins, reduced sulfur and deprotonated amines. Oxidation of fluoroquinolone antibiotics, ciprofloxacin (CIP) and enrofloxacin (ENR), by Fe(VI) were investigated for their reaction products and toxicity changes as well as biodegradability of these products. Ten products were identified for both CIP and ENR reactions with Fe(VI) using a high-resolution accurate-mass Orbitrap mass analyzer. Structural changes to the CIP and ENR molecule included dealkylation, formation of alcohols and amides in piperazine ring and oxygen transfer to the double bond in quinolone structure. An enamine formation mechanism was tentatively proposed to facilitate the interpretation of CIP and ENR oxidation pathways. Toxicity evaluation using Microbial Assay for toxicity Risk Assessment (MARA) bioassay indicated that Fe(VI) oxidation products of CIP and ENR contributed negligible antibacterial potency and Fe(VI) oxidation treatment can remove the residual toxicity of CIP and ENR impacted source waters. The Fe(VI) oxidation treatment resulted in formation of relatively more biodegradable products (based on in silico assessment) than their corresponding parent compounds. The results showed that Fe(VI) has a good potential to degrade fluoroquinolone antibiotics and their antimicrobial potency in natural waters. SN - 1873-3336 UR - https://www.unboundmedicine.com/medline/citation/27565854/Oxidation_of_ciprofloxacin_and_enrofloxacin_by_ferrate_VI_:_Products_identification_and_toxicity_evaluation_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0304-3894(16)30762-2 DB - PRIME DP - Unbound Medicine ER -