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Mechanistic study of the electrochemical oxidation of fluoroquinolones: Ciprofloxacin, danofloxacin, enoxacin, levofloxacin and lomefloxacin.

フルオロキノロン系抗菌薬の電気化学的酸化における分解機構の解明

other not specified not assessed

Abstract

Five fluoroquinolone antibiotics—ciprofloxacin, danofloxacin, enoxacin, levofloxacin, and lomefloxacin—were subjected to electrochemical oxidation in a micro-flow reactor fitted with a boron-doped diamond (BDD) electrode. High-performance high-resolution chromatography coupled with multifragmentation mass spectrometry identified 15 novel transformation products. In silico quantitative structure-activity relationship analysis predicted that nearly all transformation products carried lower ecotoxicity than the parent compounds. Three voltage-dependent degradation mechanisms were distinguished: at approximately 1 V, molecular hydrogen was eliminated from the piperazine moiety; at approximately 1.25 V, methyl and methylene groups were removed; and at 1.5 V, hydroxyl radicals generated at the BDD electrode drove substitution reactions at the piperazine ring. These findings advance mechanistic understanding of electrochemical oxidation as an approach to removing fluoroquinolone micropollutants from aquatic environments.

Mechanism

Fluoroquinolone degradation proceeds via three voltage-dependent pathways: molecular hydrogen elimination from the piperazine moiety at ~1 V, methyl/methylene group removal at ~1.25 V, and hydroxyl radical-mediated substitution at the piperazine ring at 1.5 V, with hydroxyl radicals generated at the BDD electrode.

Bibliographic

Authors
Voigt M, Dluziak JM, Wellen N, Jaeger M
Journal
Chemosphere
Year
2024
PMID
38522672
DOI
10.1016/j.chemosphere.2024.141763

Tags

Mechanism:ヒドロキシルラジカル消去

Delivery context

The delivery route is not clearly identifiable from this paper. For hydrogen intake, inhalation is the most efficient route; inhalation, however, carries explosion risk (empirical LFL of 10%; high-concentration devices are not recommended).

Safety notes

The delivery route is not clearly identifiable from this paper. For hydrogen intake, inhalation is the most efficient route; inhalation, however, carries explosion risk (empirical LFL of 10%; high-concentration devices are not recommended).

See also:

Cite as: H2 Papers — PMID 38522672. https://h2-papers.org/en/papers/38522672
Source: PubMed PMID 38522672