Transformation of lamotrigine by white-rot fungus Pleurotus ostreatus

Chefetz, Benny; Marom, Rotem; Salton, Orit; Oliferovsky, Mariana; Mordehay, Vered; Ben-Ari, Julius; Hadar, Yitzhak

doi:10.1016/j.envpol.2019.04.057

Cited by 21 publications

(23 citation statements)

References 43 publications

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“…It is interesting to note that in the bisolute systems, all TPs exhibited higher masses than lamotrigine, except two isomers of TP222. Oxidation of vanillic acid and o -methoxyphenol by redox-active mineral surfaces has been reported to be accompanied by the formation of free radicals and polymerization, resulting in products with higher masses than the reactants. , It is interesting to note that out of all products detected, only two TPs (TP272lamotrigine- N2 -oxide, and TP314) were identical to those in abiotic systems and a system of biological transformation of lamotrigine …”

Section: Results and Discussionmentioning

confidence: 99%

“…The fragmentation pattern includes a radical fragment with m / z 242.0132, formed by a loss of NO (Figure S2E), indicating the addition of oxygen to the triazine nitrogen to form lamotrigine-N2-oxide. Lamotrigine-N2-oxide is known as a human metabolite that is formed in treated wastewater and in advanced oxidation processes such as ozonation and reaction with hydroxyl radical. ,, Oxidation of lamotrigine by white-rot fungus also results in the formation of lamotrigine- N2 -oxide, which is the only TP formed in both these biotic and single-solute abiotic systems …”

Section: Results and Discussionmentioning

confidence: 99%

“…The persistence of environmental pollutants is commonly determined by the compound’s stability in biotic systems, leaving out abiotic factors, which also can influence pollutants’ environmental fate, as suggested in this work. The similarity in TPs of biotic and abiotic transformations of lamotrigine might indicate close pathways of the pollutant degradations, whereas variations in the TPs suggest differences in biotic and abiotic reaction mechanisms . Elucidating the efficiency and mechanisms of these processes and detailed characterization of the TPs behavior will help to select the optimal methods of soil and water decontamination.…”

Section: Results and Discussionmentioning

confidence: 99%

“…Lamotrigine’s benzene moiety is relatively deactivated by two electron-withdrawing chlorine atoms. Nevertheless, it forms conjugates via the benzene ring (and via the triazine moiety) during biotransformation induced by the white-rot fungus Pleurotus ostreatus …”

Section: Introductionmentioning

confidence: 99%

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Abiotic Transformation of Lamotrigine by Redox-Active Mineral and Phenolic Compounds

Karpov

Seiwert

Mordehay

et al. 2021

Environ. Sci. Technol.

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The anticonvulsant drug lamotrigine is a recalcitrant environmental pollutant. It was detected in drinking water, surface water, reclaimed wastewater, arable soils, and even in edible crops. In this work, we studied the mechanisms of lamotrigine transformation by a common redox soil mineral, birnessite, in a single-solute system and in bisolute systems with vanillic acid or o-methoxyphenol. In the single-solute system, 28% of lamotrigine was transformed and 14 transformation products (TPs) were identified. Based on a detailed analysis of the TPs, we suggested that lamotrigine is transformed mainly by oxidation, addition, and dechlorination reactions. In the bisolute systems, the redox-active phenolic compounds enhanced the elimination and transformation of lamotrigine. Vanillic acid was more efficient, generating 92% transformation of lamotrigine (58 TPs were identified), whereas o-methoxyphenol induced 48% transformation (35 TPs were identified). In the bisolute system with phenolic compounds, lamotrigine has possibly been transformed mainly via addition reactions with phenolic compounds and their oxidation products (protocatechuic acid, quinone, and oligomers). Thus, masses of the formed TPs were elevated as compared to the parent compound. The current study demonstrates the important role of redox-active minerals and naturally occurring phenolic compounds in abiotic removal and transformation of a recalcitrant environmental pollutant.

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Section: Results and Discussionmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Abiotic Transformation of Lamotrigine by Redox-Active Mineral and Phenolic Compounds

Karpov

Seiwert

Mordehay

et al. 2021

Environ. Sci. Technol.

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“…Also, for each compound described above, the experiments were conducted increasing concentrations of each antiepileptic at nominal concentrations of 10, 100, and 1000 µg/L. These concentrations were based on the environmental concentration of GAB of 0.1 to 10 µg/L (Li et al, 2018) and the environmental concentration of LTG of 1 to 10 μg/L (Chefetz et al, 2019).…”

Section: Modified Fish Embryo Acute Toxicity Test (Oecd 236)mentioning

confidence: 99%

Antiepileptic Drugs Cause Lethal, Sublethal, Teratogenic Effects and Morphometric Parameters on Embryos and Larvae of Zebrafish (Danio Rerio)

Martins

Cadena

2020

Rease

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No presente estudo, avaliamos os efeitos tóxicos das drogas antiepilépticas gabapentina (GAB), fenobarbital (PB), oxcarbazepina (OX) e lamotrigina (LTG), os efeitos letais, subletais, teratogênicos e parâmetros morfométricos em embriões e larvas de peixe-zebra (Danio ri). Um teste de toxicidade aguda foi realizado usando embriões de D. rerio de acordo com as diretrizes OECD 236 (2013). O teste de toxicidade aguda revelou que a mortalidade de animais aumentou com o passar do tempo (24 a 96 hpf) em animais expostos a GAB, PB, OX e LTG. Os efeitos subletais tiveram uma variação significativa (p <0,05) no número de batimentos cardíacos, não de forma dependente da dose. Também foi possível observar variação na pigmentação em todos os animais e a presença de edema pericárdico em alguns grupos. Os efeitos teratogênicos revelaram malformação da cabeça apenas nos animais expostos ao GAB. Além disso, deformação da cauda, deformação da coluna, edema do saco vitelino e bexiga natatória inflada foram observados em todos os animais. Os parâmetros morfométricos tiveram uma diminuição (p <0,05) no comprimento corporal, largura da cabeça, distância ocular, distância entre os olhos e diâmetro do olho em todos os grupos no 96 hpf. Foi observado que gabapentina, fenobarbital, oxcarbazepina e lamotrigina induzem efeitos letais, subletais, teratogênicos e alterações morfométricas no peixe-zebra.

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Apparent and true mineralization during combined electro‐oxidation and electro‐coagulation on stainless steel anode

Meena

Ghatak

2023

Asia-Pacific J Chem Eng

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Present study is a novel attempt to experimentally verify that electrochemical treatment of organic pollutants on stainless steel (SS) anode is a combination of electro‐oxidation (EO) and electro‐coagulation (EC) with quantitative estimation of individual contributions of the two mechanisms. Target organic pollutants, metformin HCl (MET‐HCl) and lamotrigine (LAM), were electrochemically treated with SS anode for this purpose. Experiments were designed using central composite rotatable design (CCRD) to assess the effect of current density (CD) and supporting electrolyte concentration (SEC) as independent process parameters. Under all conditions, the process was experimentally verified to be a combination of EO and EC. For MET‐HCl, true mineralization (TM) as a result of EO contribution varied between 50.13% and 66.64%. EO contribution and resulting TM for LAM ranged from 37.5% to 61.83%. EC contributed 30.6%–31.84% towards MET‐HCl remediation causing the TOC to be transferred from the liquid to the sludge produced (SP). EC contribution was 23.68%–35.89% for LAM remediation. Thus, apparent mineralization (AM), the sum of EO and EC contributions, ranged from 80.63% to 97.79% for MET‐HCl and 61.18% to 96.82% for LAM.Process parameters were statistically optimized using response surface methodology (RSM) to simultaneously maximize TM and AM with minimal energy consumption and maximal current efficiency. The optimized conditions were 0.83 mA/cm2 CD and 86.66 ppm SEC for MET‐HCl. The corresponding values were 1.31 mA/cm2 CD and 79.51 ppm SEC for LAM.

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Transformation of lamotrigine by white-rot fungus Pleurotus ostreatus

Cited by 21 publications

References 43 publications

Abiotic Transformation of Lamotrigine by Redox-Active Mineral and Phenolic Compounds

Abiotic Transformation of Lamotrigine by Redox-Active Mineral and Phenolic Compounds

Antiepileptic Drugs Cause Lethal, Sublethal, Teratogenic Effects and Morphometric Parameters on Embryos and Larvae of Zebrafish (Danio Rerio)

Apparent and true mineralization during combined electro‐oxidation and electro‐coagulation on stainless steel anode

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