The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
Oxidative Transformation of Fluoroquinolone Antibacterial Agents and Structurally Related Amines by Manganese Oxide
Abstract
Various members of the popular fluoroquinolone antibacterial agents (FQs) have been frequently detected in municipal wastewater and surface water bodies in recent years. This study was conducted to gain a better understanding of the fate of FQs in the sediment-water environment. Seven FQs were examined for adsorptive and oxidative interactions with delta-MnO2 under environmental conditions and exhibited reactivity in the order of ciprofloxacin approximately enrofloxacin approximately norfloxacin approximately ofloxacin > lomefloxacin > pipemidic acid >> flumequine. Four amines that are structurally related to the aniline and piperazine functional groups of FQs showed reactivity to oxidation by delta-MnO2 in the order of 1-phenylpiperazine > aniline > N-phenylmorpholine > 4-phenylpiperidine. Comparison among the above compounds clearly indicates thatthe piperazine moiety of FQs is the predominant adsorptive and oxidative site to MnO2. Product analyses showed that oxidation by MnO2 results in dealkylation and hydroxylation at the piperazine moiety of FQs, with the quinolone ring essentially intact. The reaction kinetics, reactivity comparison, and product characterization point to a surface reaction mechanism that likely begins with formation of a surface complex between FQ and the surface-bound MnIV, followed by oxidation at the aromatic N1 atom of FQ's piperazine moietyto generate an anilinyl radical intermediate. The radical intermediates subsequently undergo N-dealkylation, C-hydroxylation, and possibly coupling to yield a range of products. Even though the quinolone ring appears to be stable with respect to MnO2, it affects the overall reactivity and potentially product distribution of FQs via substituent effects. Results of this study strongly suggest that manganese oxides commonly present in soils will likely play an important role in the abiotic degradation of fluoroquinolone antibacterial agents in the environment.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cites
Kolpin, D. W., Furlong, E. T., Meyer, M. T., Thurman, E. M., Zaugg, S. D., Barber, L. B., & Buxton, H. T. (2002) · Environmental Science & Technology · doi:10.1021/es011055j · Cited by 7,953
Cited by
Fluoroquinolone antibiotics: An emerging class of environmental micropollutants
Van Doorslaer, X., Dewulf, J., Van Langenhove, H., & Demeestere, K. (2014) · Science of The Total Environment · doi:10.1016/j.scitotenv.2014.08.075 · Cited by 819
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
A critical review of the reactivity of manganese oxides with organic contaminants
Remucal, C. K., & Ginder-Vogel, M. (2014) · Environmental Science: Processes & Impacts · doi:10.1039/c3em00703k · Cited by 375
Paul, T., Dodd, M. C., & Strathmann, T. J. (2010) · Water Research · doi:10.1016/j.watres.2010.03.002 · Cited by 368
Oxidative Removal of Bisphenol A by Manganese Dioxide: Efficacy, Products, and Pathways
Lin, K., Liu, W., & Gan, J. (2009) · Environmental Science & Technology · doi:10.1021/es900235f · Cited by 337
Mn-based catalysts for sulfate radical-based advanced oxidation processes: A review
Huang, J., & Zhang, H. (2019) · Environment International · doi:10.1016/j.envint.2019.105141 · Cited by 328
Self-citationWang, L., Jiang, J., Pang, S.-Y., Zhou, Y., Li, J., Sun, S., Gao, Y., & Jiang, C. (2018) · Chemical Engineering Journal · doi:10.1016/j.cej.2018.07.103 · Cited by 293
Spahr, S., Teixidó, M., Sedlak, D. L., & Luthy, R. G. (2020) · Environmental Science: Water Research & Technology · doi:10.1039/c9ew00674e · Cited by 153
Metadata
- Authors
- Zhang, H., & Huang, C.-H.
- Venue
- Environmental Science & Technology
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-05-11
- Volume
- 39
- Issue
- 12
- Pages
- 4474-4483
- ISSN
- 0013-936X (ISSN-L)
- 1520-5851
- OpenAlex
- W2023830578
- Cited by
- 355
- References
- 1
- FWCI
- 6.48
- Type
- journal article
- Language
- en
- Open access
- closed
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
Data sources
Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
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.
