Product identification and toxicity change during oxidation of methotrexate by ferrate and permanganate in water

doi:10.1007/s11783-021-1501-8

Front. Environ. Sci. Eng.

2022, Vol. 16

Issue (7) : 93 https://doi.org/10.1007/s11783-021-1501-8

RESEARCH ARTICLE

Product identification and toxicity change during oxidation of methotrexate by ferrate and permanganate in water

Shengqi Zhang¹, Chengsong Ye¹, Wenjun Zhao², Lili An¹, Xin Yu¹, Lei Zhang^3,⁴, Hongjie Sun², Mingbao Feng¹(

)

¹. College of the Environment & Ecology, Xiamen University, Xiamen 361102, China
². College of Geography and Environmental Science, Zhejiang Normal University, Jinhua 321004, China
³. State Key Laboratory of Cellular Stress Biology, Innovation Center for Cell Signaling Network, School of Life Sciences, Xiamen University, Xiamen 361102, China
⁴. Core Facility of Biomedical, Xiamen University, Xiamen 361102, China

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Abstract

• Oxidation of methotrexate by high-valent metal-oxo species was first explored.

• Fe(VI) presented a higher reactivity to MTX than Mn(VII) at pH 8.0.

• Ketonization and cleavage of peptide bond were two initial reaction pathways.

• Products of MTX were not genotoxic, neurotoxic, or endocrine-disrupting chemicals.

• The less biodegradable products exhibited developmental and acute/chronic toxicity.

Accompanying an annual increase in cancer incidence, the global use of anticancer drugs has remarkably increased with their worldwide environmental prevalence and ecological risks. In this study, the oxidation of methotrexate (MTX), a typical anticancer drug with ubiquitous occurrence and multi-endpoint toxicity, by ferrate(VI) (Fe(VI)) and permanganate (Mn(VII))) was investigated in water. Fe(VI) exhibited a higher reactivity with MTX (93.34 M⁻¹ s⁻¹) than Mn(VII) (3.01 M⁻¹ s⁻¹) at pH 8.0. The introduction of Cu(II) and Fe(III) at 1.0 mM improved the removal efficiency of 5.0 μM MTX by 100.0 μM Fe(VI) from 80% to 95% and 100% after 4 min, respectively. Seven oxidized products (OPs) were identified during oxidative treatments, while OP-191 and OP-205 were characterized as specific products for Fe(VI) oxidation. Initial ketonization of the L-glutamic acid moiety and cleavage of the peptide bond of MTX were proposed. Additionally, a multi-endpoint toxicity evaluation indicated no genotoxicity, neurotoxicity, or endocrine-disrupting effects of MTX and its OPs. Particularly, serious developmental toxicity in zebrafish larvae was observed in the treated MTX solutions. Based on the acute and chronic aquatic toxicity prediction, OP-190, OP-192, OP-206, and OP-208 were deemed toxic or very toxic compared to harmful MTX. Furthermore, the reduced biodegradability index from 0.15 (MTX) to −0.5 to −0.2 (OP-192, OP-206, and OP-468) indicated the formation of lower biodegradable OPs. Overall, this study suggests that Fe(VI) and Mn(VII) oxidation are promising treatments for remediating anticancer drug-contaminated water. However, the environmental risks associated with these treatments should be considered in the evaluation of water safety.

Keywords Anticancer drugs High-valent metal-oxo species Oxidation kinetics Reaction mechanisms Multi-endpoint toxicity

Corresponding Author(s): Mingbao Feng

Issue Date: 23 November 2021

Cite this article:

Shengqi Zhang,Chengsong Ye,Wenjun Zhao, et al. Product identification and toxicity change during oxidation of methotrexate by ferrate and permanganate in water[J]. Front. Environ. Sci. Eng., 2022, 16(7): 93.

URL:

https://academic.hep.com.cn/fese/EN/10.1007/s11783-021-1501-8
https://academic.hep.com.cn/fese/EN/Y2022/V16/I7/93

Fig.1 Removal of MTX by Fe(VI) (a) and Mn(VII) (b) as a function of reaction time in water, and the effect of five different water components (i.e., Cu(II), Fe(III), HCO₃⁻, Cl⁻, and HA) on the removal of MTX by Fe(VI) ((c) reaction time= 4 min) and Mn(VII) ((d) reaction time= 1 h). (Experimental conditions: [MTX]₀ = 5.0 μM, [Fe(VI)]₀ = [Mn(VII)]₀ = 100.0 μM, pH 8.0 (10.0 mM phosphate buffer), [Cu(II)] = [Fe(III)] = [HCO₃⁻] = [Cl⁻] = 1.0 mM, and [HA] = 10.0 mg/L).

Tab.1 Accurate mass measurements of MTX and its OPs by Fe(VI) and Mn(VII), which were determined by LC-MS/MS (ESI positive and ESI negative)

Fig.2 (a) The proposed reaction pathways of MTX by Fe(VI) and Mn(VII) in water. (Experimental conditions: [MTX]₀ = 5.0 μM, [Fe(VI)]₀ = [Mn(VII)]₀ = 100.0 μM, pH 8.0 (10.0 mM phosphate buffer); specifically, the reaction time for Fe(VI) and MTX was 4 min, and the reaction time for Mn(VII) and MTX was 1 h, which corresponded to 20%-40% removal of MTX), (b) the predicted biodegradability of different OPs generated from MTX oxidation by Fe(VI) and Mn(VII) using Biowin 5, and (c) the predicted acute/chronic toxicity of different OPs on fish, daphnid, and green algae using ECOSAR.

Fig.3 The genotoxicity evaluation of the reaction solutions of MTX by Fe(VI) and Mn(VII) at pH 8.0 using the SOS/umu tests ((a) the positive control with 4-NQO at 50, 100, 150, and 200 ng/L; (b) MTX at different concentrations (i.e., 10.0 ng/L−1.0 mg/L); (c) the reaction solutions of MTX by Fe(VI) at different time; (d) the reaction solutions of MTX by Mn(VII) at different time).

Fig.4 Morphological abnormalities in zebrafish larvae at 96 hpf. (a) the well-developed larvae for control; (b) the well-developed larvae for Fe(VI)-decayed sample; (c) the well-developed larvae for Mn(VII)-decayed sample; (d) the deformity of zebrafish larvae for MTX; (e) the deformity of zebrafish larvae for Fe(VI) + MTX; and (f) the deformity of zebrafish larvae for Mn(VII) + MTX. Notably, the red arrow indicated that edema appeared in the hearts and yolk sac area, while the blue arrow suggested the scoliosis deformity and tail. Scale bars correspond to 250 μm.

Fig.5 Moving distance of zebrafish larvae at 120 hpf after 9 min of exposure to control and MTX before and after oxidation of Fe(VI) and Mn(VII). All samples obtained from the degradation experiments were diluted 100-time into the exposure media.

Tab.2 In silico QSAR predictions of MTX and its OPs for multi-endpoint toxicity

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