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Oxidation of danofloxacin by free chlorine—kinetic study, structural identification of by-products by LC–MS/MS and potential toxicity of by-products using in silico test

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Abstract

In this study, we aimed to investigate the kinetics and the mechanism of reaction of the fluoroquinolone antibacterial danofloxacin (DANO) by free available chlorine (FAC) during water chlorination process. Kinetic study was thus performed at pH 7.2, 20 °C in the presence of an excess of total chlorine. Under these experimental conditions, a second-order reaction rate constant (first-order relative to DANO concentration and first-order relative to FAC concentration) was evaluated to k~1446 M−1 s−1. Five degradation products were identified at different reaction times. Their structures were investigated by using fragmentations obtained at different CID collision energies in MS/MS experiments. Moreover, the toxicity of the proposed structures was predicted by using T.E.S.T. program. The results indicated that all by-products may have a developmental toxicity. The oral rat LD50 concentration was predicted to be lower than that of DANO. Furthermore, two degradation compounds presented a concentration level for fathead minnow LC50 (96 h) lower than that of DANO and presented toxicity for the marine animals.

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Acknowledgement

We would to thanks the CNRSL–LAEC to host this research experiments in their laboratories. MY gratefully acknowledges Lebanese University for the Ph.D. grant. This study also benefitted from supports from the French National Research Agency (ANR) as part of the Investments for the Future Program, within the Cluster of Excellence COTE (ANR-10-LABX-45)

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Authors and Affiliations

  1. National Council of Scientific Research (CNRS)—Lebanese Atomic Energy Commission (LAEC), Laboratory of Analysis of Organic Pollutants (LAOP), 11-8281, Riad El Solh, Beirut, 1107 2260, Lebanon

    Montaha Yassine, Ahmad Rifai & Mohamad Al Iskandarani

  2. EPOC, L’équipe de Physico et Toxico Chimie de l’Environnement, University of Bordeaux, UMR 5805, 33400, Talence, France

    Montaha Yassine, Aurélien Trivella, Patrick Mazellier & Hélène Budzinski

  3. CNRS, EPOC, UMR5805, 33400, Talence, France

    Montaha Yassine, Aurélien Trivella, Patrick Mazellier & Hélène Budzinski

  4. Dr. Faculté de Santé Publique, Section I, Hadath, Beyrouth, Lebanon

    Montaha Yassine, Samah Doumyati & Mohamad Al Iskandarani

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  1. Montaha Yassine
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  2. Ahmad Rifai
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  7. Mohamad Al Iskandarani
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Correspondence to Mohamad Al Iskandarani.

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Yassine, M., Rifai, A., Doumyati, S. et al. Oxidation of danofloxacin by free chlorine—kinetic study, structural identification of by-products by LC–MS/MS and potential toxicity of by-products using in silico test. Environ Sci Pollut Res 24, 7982–7993 (2017). https://doi.org/10.1007/s11356-017-8409-7

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  • DOI: https://doi.org/10.1007/s11356-017-8409-7

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