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Cephalexin degradation initiated by OH radicals: theoretical prediction of the mechanisms and the toxicity of byproducts

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Abstract

In this work, the density functional theory is used to study the local reactivity of cephalexin (CLX) to radical attack and explain the mechanism of the reaction between CLX and hydroxyl radical attack leading to degradation byproducts. The reaction between •OH and CLX is supposed to lead to either an addition of a hydroxyl radical or an abstraction of a hydrogen. The results showed that the affinity of cephalexin for addition reactions increases as it passes from the gas to the aqueous phase and decreases as it passes from the neutral to the ionized form. Thermodynamic data confirmed that OH addition radicals (Radd) are thermodynamically favored over H abstraction radicals (Rabs). The ecotoxicity assessments of CLX and its byproducts are estimated from the acute toxicities toward green algae, Daphnia, and fish. The formation of byproducts is safe for aquatic organisms, and only one byproduct is harmful to Daphnia.

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Data availability

The datasets generated and/or analyzed during the current study are available from the corresponding author on reasonable request.

Code availability

Gaussian 16 program package: G16W Full Version, 32-Bit, Rev: A.03 Front: 1.1. Version: Multiprocessor. GaussView6 for Windows, Rev: 6.0.16, 32-bit. V32108462166828W-4627 N. ECOSAR Class Program (Free Ware).

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Funding

This study was financially supported by the General Directorate of Scientific Research and Technological Development (DGRSDT) of Algeria through the national research program (PRFU N° B00L01UN180120220001).

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Authors and Affiliations

  1. Laboratory of Chemistry and Environmental Chemistry LCEE, Department of Chemistry, Faculty of Material Sciences, University of Batna 1, 05000, Batna, Algeria

    R. Masmoudi, S. Khettaf, A. Soltani & A. Dibi

  2. Laboratory of Applied Energy and Materials (LEAM), University of Jijel, BP. 98, Ouled Aissa, 18000, Jijel, Algeria

    L. Messaadia

  3. Laboratory of Interaction Materials and Environment (LIME), University of Jijel, BP. 98, Ouled Aissa, 18000, Jijel, Algeria

    M. Benamira

Authors
  1. R. Masmoudi
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  2. S. Khettaf
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  3. A. Soltani
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  4. A. Dibi
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  5. L. Messaadia
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  6. M. Benamira
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Contributions

R. Masmoudi: investigation, methodology, writing—original draft, writing—reviewing and editing. S. Khettaf: methodology, validation. A. Soltani: formal analysis, validation. A. Dibi: conceptualization, validation. L. Messaadia: software, formal analysis. M. Benamira: supervision, validation, writing—reviewing and editing.

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Correspondence to L. Messaadia or M. Benamira.

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Masmoudi, R., Khettaf, S., Soltani, A. et al. Cephalexin degradation initiated by OH radicals: theoretical prediction of the mechanisms and the toxicity of byproducts. J Mol Model 28, 141 (2022). https://doi.org/10.1007/s00894-022-05121-y

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