Application of enantiomeric fractions in environmental forensics: Uncertainties and inconsistencies

Sanganyado, Edmond; Lu, Zhijiang; Liu, Wenhua

doi:10.1016/j.envres.2020.109354

Cited by 17 publications

(4 citation statements)

References 118 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Finally, most of the COVID-19 related pharmaceuticals such as chloroquine, fluoxetine, tramadol, ritonavir, oseltamivir, and remdesivir are chiral compounds with at least one chiral centre. Enantiomers of chiral pharmaceuticals often have different toxicities; hence, pharmaceuticals should be treated as mixtures rather than single compounds (Sanganyado et al, 2017(Sanganyado et al, , 2020. Recent studies explored the use of molecular docking in determining the risk of pollutants using adverse outcome pathway approach.…”

Section: Environmental Risk Assessmentmentioning

confidence: 99%

COVID-19 drugs in aquatic systems: a review

et al. 2022

Self Cite

View full text Add to dashboard Cite

The outbreak of the human coronavirus disease 2019 (COVID-19) has induced an unprecedented increase in the use of several old and repurposed therapeutic drugs such as veterinary medicines, e.g. ivermectin, nonsteroidal anti-inflammatory drugs, protein and peptide therapeutics, disease-modifying anti-rheumatic drugs and antimalarial drugs, antiretrovirals, analgesics, and supporting agents, e.g. azithromycin and corticosteroids. Excretion of drugs and their metabolites in stools and urine release these drugs into wastewater, and ultimately into surface waters and groundwater systems. Here, we review the sources, behaviour, environmental fate, risks, and remediation of those drugs. We discuss drug transformation in aquatic environments and in wastewater treatment systems. Degradation mechanisms and metabolite toxicity are poorly known. Potential risks include endocrine disruption, acute and chronic toxicity, disruption of ecosystem functions and trophic interactions in aquatic organisms, and the emergence of antimicrobial resistance.

show abstract

Section: Environmental Risk Assessmentmentioning

confidence: 99%

COVID-19 drugs in aquatic systems: a review

et al. 2022

Self Cite

View full text Add to dashboard Cite

show abstract

“…Influent or untreated wastewater typically contains ibuprofen and naproxen at µg L −1 concentrations and flurbiprofen and ketoprofen at sub-µg L −1 concentrations (Camacho-Muñoz et al 2014;Gardner et al 2013;Kasprzyk-Hordern et al 2009;Larsson et al 2014;Petrie et al 2015;Roberts and Thomas 2006). The enantiomeric composition of chiral drugs is typically reported as enantiomeric fraction (Sanganyado et al 2020). The enantiomeric fraction of chiral NSAIDs can be calculated using Eq.…”

Section: Influent Wastewatermentioning

confidence: 99%

Analysis, fate and toxicity of chiral non-steroidal anti-inflammatory drugs in wastewaters and the environment: a review

Petrie

Camacho‐Muñoz

2020

Environ Chem Lett

View full text Add to dashboard Cite

Non-steroidal anti-inflammatory drugs (NSAIDs) are found in the aquatic environment globally. Such drugs including naproxen, ibuprofen and ketoprofen are chiral molecules. Enantiomers of those drugs have identical physicochemical properties but can behave and interact differently in chiral environments due to differences in their three-dimensional shape. This results in enantiospecific differences in environmental fate and toxicity, which is often overlooked. Therefore, we review the analytical methods, occurrence and fate, and toxicity of chiral non-steroidal anti-inflammatory drugs at the enantiomeric level. The advancement of enantioselective chromatography methods, particularly the use of polysaccharide-based stationary phases, has enabled trace determination of enantiomers in complex environmental matrices. Macrocosm and microcosm studies of engineered and natural environments revealed that such drugs can undergo both enantioselective degradation and chiral inversion. Enantioselectivity has been reported during wastewater treatment, in surface waters and in agricultural soils. The use of microcosms spiked with individual enantiomers over racemates is essential to evaluate these degradation and inversion fate processes. The chiral inversion process whereby one enantiomer converts into its antipode can be significant if the more toxic enantiomers are formed. Existing enantiospecific effect studies report less than an order of magnitude difference in enantiomer toxicity. However, toxicity data for enantiomers are limited and further research is needed to better appreciate the environmental risk at the enantiomeric level.

show abstract

“…Currently, at least 40% of commonly used pesticides have a chiral structure, and most are still sold and used in racemic form [ 6 ]. However, enantiomers contained in chiral pesticides have significant differences in biological effects such as enrichment, metabolism, lethality, teratogenicity, and endocrine disruption [ 7 ]. Synthetic pyrethroids (SPs) are a typical type of chiral pesticide, being one of the most widely used, efficient, and low-toxicity insecticides on the market, with a top three market share [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Toxicity of Tetramethrin to Different Developmental Stages of Zebrafish (Danio rerio)

Feng,

Xu,

Huang

et al. 2024

Toxics

View full text Add to dashboard Cite

Chiral pesticides exhibit enantioselective differences in processes such as biological absorption, metabolism, and toxic effects. Organisms have different physiological characteristics at different developmental stages. Therefore, conducting enantiomeric toxicity studies at different developmental stages of organisms can help deepen the understanding of the ecological effects of chiral pesticides. This study focused on trans-tetramethrin (Tet) and investigated the enantioselectivity in bioconcentration, developmental toxicity, estrogenic effects, and immunotoxicity of Tet’s racemate ((±)-Tet) and its two enantiomers ((+)-Tet and (−)-Tet) in three developmental stages of zebrafish: embryos, yolk sac larvae, and juveniles. The results showed that Tet exhibited different enantioselectivity in lethal, bioconcentration, and teratogenic effects on zebrafish at different developmental stages. The LC50 value was (+)-Tet > (±)-Tet > (−)-Tet, with embryos being the most sensitive, followed by juveniles and yolk sac larvae. The enantioselective bioconcentration was (±)-Tet > (+)-Tet > (−)-Tet, and the bioconcentration effect was greater in embryos than that in yolk sac larvae and juveniles. Developmental toxicity indicated that (+)-Tet and (±)-Tet had higher teratogenic effects on yolk sac larvae than on embryos. Tet exhibited different enantioselective effects on the expression of zebrafish estrogen-related genes and innate immune-related genes at different developmental stages. These results will contribute to a more comprehensive assessment of the aquatic toxicity and environmental risks of chiral pesticides.

show abstract

Application of enantiomeric fractions in environmental forensics: Uncertainties and inconsistencies

Cited by 17 publications

References 118 publications

COVID-19 drugs in aquatic systems: a review

COVID-19 drugs in aquatic systems: a review

Analysis, fate and toxicity of chiral non-steroidal anti-inflammatory drugs in wastewaters and the environment: a review

Enantioselective Toxicity of Tetramethrin to Different Developmental Stages of Zebrafish (Danio rerio)

Contact Info

Product

Resources

About