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Ozonation of Ciprofloxacin in Water: HRMS Identification of Reaction Products and Pathways
Abstract
Degradation products formed during ozonation of an aqueous solution of the antibiotic ciprofloxacin in a bubble column are analyzed by HPLC-UV high-resolution mass spectrometry. Based on the identification of the reaction products, reaction pathways are proposed starting with (1) degradation at the piperazinyl substituent, (2) degradation at the quinolone moiety with formation of isatin analogues, and (3) degradation at the quinolone moiety with formation of anthranilic acid analogues. Unlike H2O2 addition (10 microM), pH (3,7, and 10) strongly affects degradation product formation during ozonation. Degradation at the quinolone core is favored at pH 7. Addition of t-butanol, a hydroxyl radical scavenger, ruled out formation of isatin and anthranilic acid analogues. Because the carboxylic group and the keto group at the quinolone moiety are essential for antibacterial activity, degradation at pH 7 seems to be promising for reduction of bacterial resistance against quinolones in contaminated water.
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Cited by
Removal of pharmaceuticals and personal care products (PPCPs) from wastewater: A review
Wang, J., & Wang, S. (2016) · Journal of Environmental Management · doi:10.1016/j.jenvman.2016.07.049 · Cited by 1,430
Hollender, J., Zimmermann, S. G., Koepke, S., Krauss, M., McArdell, C. S., Ort, C., Singer, H., von Gunten, U., & Siegrist, H. (2009) · Environmental Science & Technology · doi:10.1021/es9014629 · Cited by 870
An, T., Yang, H., Li, G., Song, W., Cooper, W. J., & Nie, X. (2010) · Applied Catalysis B: Environmental · doi:10.1016/j.apcatb.2009.12.002 · Cited by 649
Adsorption of ciprofloxacin on surface-modified carbon materials
Carabineiro, S. A. C., Thavorn-Amornsri, T., Pereira, M. F. R., & Figueiredo, J. L. (2011) · Water Research · doi:10.1016/j.watres.2011.06.008 · Cited by 362
Prieto, A., Möder, M., Rodil, R., Adrian, L., & Marco-Urrea, E. (2011) · Bioresource Technology · doi:10.1016/j.biortech.2011.08.055 · Cited by 318
Metadata
- Authors
- DeWitte, B., Dewulf, J., Demeestere, K., Van De Vyvere, V., De Wispelaere, P., & Van Langenhove, H.
- Venue
- Environmental Science & Technology
- Publisher
- American Chemical Society (ACS)
- Published
- 2008-05-23
- Volume
- 42
- Issue
- 13
- Pages
- 4889-4895
- ISSN
- 0013-936X (ISSN-L)
- 1520-5851
- OpenAlex
- W2060575372
- Cited by
- 202
- References
- 0
- FWCI
- 9.67
- Type
- journal article
- Language
- en
- Open access
- closed
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- DeWitte, B., Dewulf, J., Demeestere, K., Van De Vyvere, V., De Wispelaere, P., & Van Langenhove, H. (2008). Ozonation of Ciprofloxacin in Water: HRMS Identification of Reaction Products and Pathways. Environmental Science & Technology. https://doi.org/10.1021/es8000689
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
