-
Journal of Hazardous Materials Jun 2023Organophosphorus flame retardants (OPFRs) have been widely used in industrial and commercial applications. Unfortunately, the chemical constituents of OPFRs,... (Review)
Review
Organophosphorus flame retardants (OPFRs) have been widely used in industrial and commercial applications. Unfortunately, the chemical constituents of OPFRs, organophosphate esters (OPEs), which have been proven to be carcinogenic and biotoxic, can release into the environment and pose potential risks to human health. This paper reviews the research progress of OPEs in the soil through bibliometric analysis and comprehensively elaborates on their pollution status, potential sources, and environmental behaviors. The OPE pollution is widely distributed in the soil at concentrations ranging from several to tens of thousands of ng/g dw. Some novel OPEs, newly discovered OPEs in the environment in recent years, are also detected. OPE concentrations vary substantially among landuses, and waste processing areas are important point sources of OPE pollution in the soil. Emission source intensity, physicochemical properties of compounds, and soil properties play important roles in the transfer process of OPEs in the soil. Biodegradation, especially microbial degradation, has potential application prospects in the remediation of OPE-contaminated soil. Brevibacillus brevis, Sphingomonas, Sphingopyxis, Rhodococcus, and other microorganisms can degrade some OPEs. This review helps clarify the pollution status of OPEs in the soil and highlights perspectives for future research.
Topics: Humans; Environmental Monitoring; Flame Retardants; Organophosphorus Compounds; Soil; Organophosphates; Esters; China
PubMed: 37030217
DOI: 10.1016/j.jhazmat.2023.131161 -
Biosensors & Bioelectronics Jun 2022The environmental accumulation of organophosphates is a serious threat to public health. To detect these xenobiotics, a broad range of sensors has been developed in past...
The environmental accumulation of organophosphates is a serious threat to public health. To detect these xenobiotics, a broad range of sensors has been developed in past decades. However, sensors with high sensitivity and a capability for degrading organophosphates are rare. In this study, "smart" whole-cell biosensors were created by combining synthetic biology approaches with the bacterial quorum sensing (QS) mechanism. The engineered whole-cell biosensor pUC57-QS-DSF-F42 L/E coli DH5α can sense a wide array of phenolic compounds including phenol and p-nitrophenol (p-NP). By optimizing the genetic circuits, the phenol and p-NP detection limits reached 0.1 and 1 μM, respectively. Importantly, by replacing the fluorescence-generated reporter sfGFP with MP-degrading enzyme PoOPH, the whole-cell biosensor pUC57-OPH-QS-DSF-F42 L/E coli DH5α actively degraded 10 and 100 μM methyl parathion (MP), a typical organophosphate pesticide, which was artificially added to the cell culture at different time points in five consecutive degrading experiments, demonstrating its MP sensing and degrading capabilities. The universal design of this new biosensor can be used to create more efficient biosensors to detect and degrade various pollutants in the environment for rapid testing and bioremediation.
Topics: Biosensing Techniques; Escherichia coli; Methyl Parathion; Nitrophenols; Organophosphates; Phenol; Quorum Sensing
PubMed: 35231682
DOI: 10.1016/j.bios.2022.114085 -
Organic & Biomolecular Chemistry Jan 2020Through the combined action of palladium catalysts and chiral phosphoric acids (CPAs) a variety of catalytic asymmetric reactions have been realized during the past... (Review)
Review
Through the combined action of palladium catalysts and chiral phosphoric acids (CPAs) a variety of catalytic asymmetric reactions have been realized during the past decade, including allylation, alkene functionalization, and C-H activation. This review surveys key examples across these various reaction types and examines the different mechanisms by which CPAs can affect stereoinduction in these reaction systems.
Topics: Catalysis; Organic Chemicals; Organophosphates; Palladium; Stereoisomerism
PubMed: 31907504
DOI: 10.1039/c9ob02205h -
The Science of the Total Environment Mar 2022Organophosphate esters (OPEs) and bisphenols are two classes of industrial chemicals that are ubiquitously detected in environmental matrices due to high global...
Organophosphate esters (OPEs) and bisphenols are two classes of industrial chemicals that are ubiquitously detected in environmental matrices due to high global production and widespread use, particularly in the manufacture of plastic products. In 2017, water samples collected throughout the highly urbanized San Francisco Bay were analyzed for 22 OPEs and 16 bisphenols using liquid chromatography-electrospray ionization-Q Trap-mass spectrometry. Fifteen of the 22 OPEs were detected, with highest median concentrations in the order TCPP (42 ng/L) > TPhP (9.5 ng/L) > TBOEP (7.6 ng/L) > TnBP (7.5 ng/L) > TEP (6.7 ng/L) > TDCIPP (6.2 ng/L). In contrast, only two of 16 bisphenols, BPA and BPS, were quantified, with concentrations ranging from <0.7-35 ng/L and <1-120 ng/L, respectively. BPA and a few OPEs (EHDPP and TEHP) were primarily present in the particulate phase, while BPS and all other observed OPEs were predominantly found in the dissolved phase. Pairwise correlation analysis revealed several strong, positive correlations among OPEs, and few weak, negative correlations between OPEs and BPA, suggesting differences between the two classes with respect to their sources, pathways, and/or fate in the environment. Concentrations of OPEs and bisphenols observed in this study were generally consistent with reported concentrations in other estuarine and marine settings globally. TDCIPP exceeded existing predicted no-effect concentrations (PNECs) at some sites, and six other compounds (TCrP, IDDPP, EHDPP, TPhP, TBOEP, and BPA) were observed at levels approaching individual compound PNECs (not considering mixture effects), indicating potential risks to Bay biota. These results emphasize the need to control releases of these contaminants in order to protect the ecosystem. Periodic monitoring can be used to maintain vigilance in the face of potential regrettable substitutions.
Topics: Bays; China; Ecosystem; Environmental Monitoring; Esters; Flame Retardants; Organophosphates; Risk Assessment; San Francisco
PubMed: 34906577
DOI: 10.1016/j.scitotenv.2021.152287 -
Environment International Jul 2022Owing to increasing concerns about the toxicity of alkyl organophosphate triesters (OPTEs), it is necessary to comprehensively profile alkyl OPTEs in the environment. In...
Owing to increasing concerns about the toxicity of alkyl organophosphate triesters (OPTEs), it is necessary to comprehensively profile alkyl OPTEs in the environment. In this study, we conducted a nontarget analysis using high-resolution mass spectrometry to newly identify alkyl OPTEs in house dust samples collected in North China. Data-independent acquisition mode directed by the characteristic phosphate fragment was used. Nine alkyl OPTEs were newly identified, namely tridecyl phosphate (TDeP), dioctyl tetradecyl phosphate, tridodecyl phosphate (TDoP), dioctyl butoxyethoxyethyl phosphate (DOBEEP), dioctyl (oxo)butoxypropyl phosphate (DOOBPP), dioctyl hydroxyethoxyethoxyethyl phosphate (DOHEEEP), didodecyl hydroxyethoxyethyl phosphate (DDoHEEP), tetradecyl dodecyl hydroxyethoxyethyl phosphate (TDoHEEP), and bis(2-butoxyethyl) hydroxyethyl phosphate (BBOEHEP). BBOEHEP was fully identified by comparison to an authentic standard, and the others were tentative structures (level 3). Eight of them (not DOHEEEP) exhibited detection frequencies between 89% and 100% in the 45 samples, and (semi-)quantitation revealed that their median concentrations and ranges were: TDoP (35.1 ng/g, 8.21-111 ng/g), DOBEEP (29.3 ng/g, 2.56-5191 ng/g), DOOBPP (13.6 ng/g, 1.38-2128 ng/g), BBOEHEP (5.79 ng/g, not detected (ND)-861 ng/g), TDeP (4.10 ng/g, 1.34-39.2 ng/g), DDoHEEP (3.26 ng/g, ND-41.5 ng/g), TDoHEEP (2.09 ng/g, ND-29.5 ng/g), and DOTP (0.93 ng/g, ND-169 ng/g). Moreover, TDeP, TDoP, DOBEEP, DOOBPP, and BBOEHEP were found in SRM2585 (standard house dust). These data revealed the widespread occurrence of alkyl OPTEs with high concentrations in the indoor environment.
Topics: Air Pollution, Indoor; Dust; Environmental Monitoring; Flame Retardants; Mass Spectrometry; Organophosphates; Phosphates
PubMed: 35687946
DOI: 10.1016/j.envint.2022.107333 -
Parasites & Vectors Dec 2023Taiwan's warm and humid climate and dense population provide a suitable environment for the breeding of pests. The three major urban insects in Taiwan are house flies,...
BACKGROUND
Taiwan's warm and humid climate and dense population provide a suitable environment for the breeding of pests. The three major urban insects in Taiwan are house flies, cockroaches, and mosquitoes. In cases where a disease outbreak or high pest density necessitates chemical control, selecting the most effective insecticide is crucial. The resistance of pests to the selected environmental insecticide must be rapidly assessed to achieve effective chemical control and reduce environmental pollution.
METHODS
In this study, we evaluated the resistance of various pests, namely, house flies (Musca domestica L.), cockroaches (Blattella germanica L. and Periplaneta americana), and mosquitoes (Aedes aegypti and Ae. albopictus) against 10 commonly used insecticides. Rapid insecticide resistance bioassays were performed using discriminating doses or concentrations of the active ingredients of insecticides.
RESULTS
Five field strains of M. domestica (L.) are resistant to all 10 commonly used insecticides and exhibit cross- and multiple resistance to four types of pyrethroids and three types of organophosphates, propoxur, fipronil, and imidacloprid. None of the five field strains of P. americana are resistant to any of the tested insecticides, and only one strain of B. germanica (L.) is resistant to permethrin. One strain of Ae. albopictus is resistant to pirimiphos-methyl, whereas five strains of Ae. aegypti exhibit multiple resistance to pyrethroids, organophosphates, and other insecticides.
CONCLUSIONS
In the event of a disease outbreak or high pest density, rapid insecticide resistance bioassays may be performed using discriminating doses or concentrations to achieve precise and effective chemical control, reduce environmental pollution, and increase control efficacy.
Topics: Animals; Insecticides; Insecticide Resistance; Taiwan; Pyrethrins; Aedes; Cockroaches; Organophosphates; Biological Assay
PubMed: 38042818
DOI: 10.1186/s13071-023-06055-x -
Chemical Research in Toxicology Dec 2021Triphenyl phosphate (TPhP) is a broad-spectrum organophosphate compound widely used as an additive in several products to prevent ignition. However, its utilization...
Triphenyl phosphate (TPhP) is a broad-spectrum organophosphate compound widely used as an additive in several products to prevent ignition. However, its utilization produces a hazardous impact on various organisms. So far, very few studies have investigated the acute toxicity of TPhP at environmentally relevant concentrations in nontarget aquatic species. This study aimed to assess whether the short-term exposure of TPhP (4, 20, and 100 μg L) affects the oxidative stress, antioxidant activity, biomolecule metabolism, DNA stability, chromosomal integrity, apoptosis, and pathological changes in various organs of fingerlings. The results illustrated that the reactive oxygen species (ROS) production and lipid peroxidation (LPO) rates were significantly higher in tissues (brain, liver, and kidney) of TPhP-treated groups. Interestingly, superoxide dismutase (SOD) and catalase (CAT) activities were remarkably decreased in tissues following TPhP exposure. The levels of protein, glucose, total cholesterol (TC), triglycerides (TG), low-density lipoprotein (LDL), and high-density lipoprotein (HDL) in various tissues were also found to be significantly altered in TPhP-exposed fish fingerlings. These significant alterations in the antioxidant system and biochemical profile induced genotoxic responses such as DNA and chromosomal damage in the fish fingerlings. Furthermore, the incidence of the observed genotoxic responses was also found to be dose-dependent. Likewise, the apoptotic responses were also significantly altered following TPhP acute exposure in fingerlings. The subsequent effects on oxidative stress, antioxidant inhibition, dysregulated biomolecule metabolism, and genotoxicity might be the possible reason for the observed pathological changes in various tissues of . Taken together, the present findings showed that the toxicity of TPhP is principally associated with exposure concentrations. Therefore, this study illustrates the toxicity risks of TPhP to vertebrate organisms at real-world concentrations.
Topics: Animals; Antioxidants; Apoptosis; Brain; Carps; DNA Damage; Dose-Response Relationship, Drug; Kidney; Lipid Peroxidation; Molecular Structure; Organophosphates; Oxidative Stress; Reactive Oxygen Species
PubMed: 34847329
DOI: 10.1021/acs.chemrestox.1c00281 -
International Journal of Hygiene and... Aug 2023Organophosphate flame retardants (OPFRs) are widely used as flame retardants and plasticizers. Laboratory evidence has suggested that maternal OPFR exposure may...
BACKGROUND
Organophosphate flame retardants (OPFRs) are widely used as flame retardants and plasticizers. Laboratory evidence has suggested that maternal OPFR exposure may adversely affect fetal growth, but the epidemiological data are limited.
OBJECTIVES
To investigate the association of maternal OPFR exposure with neonatal anthropometric measures.
METHODS
This study included 354 mother-newborn pairs from the Laizhou Wan Birth Cohort (LWBC), China. Ten OPFR metabolites were measured in maternal urine samples collected before delivery. Neonatal anthropometric data was collected from medical records and standardized into z-scores using the WHO standards (2007), including the weight-for-age (WAZ), length-for-age (LAZ), body mass index-for-age (BMIZ), weight-for-length (WLZ), and head circumference-for-age z-score (HCZ). Multiple linear regression and weighted quantile sum (WQS) regression were used to estimate the associations of individual OPFR metabolites and their mixtures with neonatal anthropometrics, respectively. Stratified analysis by sex was performed.
RESULTS
The detection rates of BCEP, DPHP, BCIPP, BDCIPP, BBOEP, DnBP and DiBP were above 60%, with median concentrations ranging from 0.14 to 3.60 μg/g creatinine. Most OPFR metabolites (i.e., BCIPP, BDCIPP, DiBP, DnBP, or BBOEP) were associated with decreased offspring WAZ and HCZ. When using WQS analysis, the OPFR metabolite mixture was inversely associated with the WAZ, BMIZ and HCZ, whereas DnBP had the highest weights. After stratified by gender, the negative associations were more pronounced among males.
CONCLUSIONS
Maternal OPFR exposure was negatively associated with offspring WAZ, BMIZ, and HCZ, and males seemed to be more vulnerable to the developmental toxicity of certain OPFRs.
Topics: Male; Infant, Newborn; Female; Humans; Maternal Exposure; Flame Retardants; Organophosphates
PubMed: 37516025
DOI: 10.1016/j.ijheh.2023.114216 -
Environmental Research May 2024Plant uptake, accumulation, and transformation of organophosphate esters (OPEs) play vital roles in their geochemical cycles and exposure risks. Here we reviewed the... (Review)
Review
Plant uptake, accumulation, and transformation of organophosphate esters (OPEs) play vital roles in their geochemical cycles and exposure risks. Here we reviewed the recent research advances in OPEs in plants. The mean OPE concentrations based on dry/wet/lipid weight varied in 4.80-3,620/0.287-26.8/12,000-315,000 ng g in field plants, and generally showed positive correlations with those in plant habitats. OPEs with short-chain substituents and high hydrophilicity, particularly the commonly used chlorinated OPEs, showed dominance in most plant samples, whereas some tree barks, fruits, seeds, and roots demonstrated dominance of hydrophobic OPEs. Both hydrophilic and hydrophobic OPEs can enter plants via root and foliar uptake, and the former pathway is mainly passively mediated by various membrane proteins. After entry, different OPEs undergo diverse subcellular distributions and acropetal/basipetal/intergenerational translocations, depending on their physicochemical properties. Hydrophilic OPEs mainly exist in cell sap and show strong transferability, hydrophobic OPEs demonstrate dominant distributions in cell wall and limited migrations owing to the interception of Casparian strips and cell wall. Additionally, plant species, transpiration capacity, growth stages, commensal microorganisms, and habitats also affect OPE uptake and transfer in plants. OPE metabolites derived from various Phase I transformations and Phase II conjugations are increasingly identified in plants, and hydrolysis and hydroxylation are the most common metabolic processes. The metabolisms and products of OPEs are closely associated with their structures and degradation resistance and plant species. In contrast, plant-derived food consumption contributes considerably to the total dietary intakes of OPEs by human, particularly the cereals, and merits specifical attention. Based on the current research limitations, we proposed the research perspectives regarding OPEs in plants, with the emphases on their behavior and fate in field plants, interactions with plant-related microorganisms, multiple uptake pathways and mechanisms, and comprehensive screening analysis and risk evaluation.
Topics: Humans; Plants; Esters; Organophosphates; Environmental Pollutants
PubMed: 38346481
DOI: 10.1016/j.envres.2024.118431 -
Environmental Science & Technology May 2023Records of the environmental occurrence of organothiophosphate esters (OTPEs), which are used as flame retardants and food and industrial additives, are unavailable. In...
Records of the environmental occurrence of organothiophosphate esters (OTPEs), which are used as flame retardants and food and industrial additives, are unavailable. In this study, we discovered three OTPEs, namely ,,-tris(2,4-di--butylphenyl) phosphorothioate (AO168═S), -butyl -(butyl-methylphenyl) -(di-butylphenyl) phosphorothioate (BBMDBPt)/,-bis(dibutylphenyl) -methyl phosphorothioate (BDBPMPt), and -butyl -ethyl -hydrogen phosphorothioate (BEHPt), in the surface water of the Yangtze River Basin by applying a characteristic phosphorothioate fragment-directed high-resolution mass spectrometry method. Among the 17 water samples tested, the detection frequencies of AO168═S and BEHPt were 100% and that of BBMDBPt/BDBPMPt was 29%. The mean concentration of AO168═S was 56.9 ng/L (30.5-148 ng/L), and semi-quantitative analysis revealed that the mean concentrations of BEHPt and BBMDBPt/BDBPMPt were 17.2 ng/L (5.5-65.4 ng/L) and 0.8 ng/L (
esters were also detected, of which the highest mean concentration was found for tris(2,4-di--butylphenyl) phosphate (AO168═O, 366 ng/L), followed by triphenyl phosphate (84.3 ng/L), triethyl phosphate (19.3 ng/L), and tributyl phosphate (15.7 ng/L). The Spearman's correlation coefficient between AO168═S and AO168═O was 0.547 ( < 0.05), suggesting that AO168═S commonly transforms into AO168═O or that these chemicals have a similar source and behavior in the environment. Future studies are warranted to assess the potential toxicity, environmental behavior, and health risks posed by OTPEs. Topics: Rivers; Esters; Organophosphates; Mass Spectrometry; Flame Retardants; Water; Organothiophosphates; Environmental Monitoring; China
PubMed: 37092689
DOI: 10.1021/acs.est.2c09416