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1.
Ecotoxicol Environ Saf ; 215: 112174, 2021 Jun 01.
Artigo em Inglês | MEDLINE | ID: mdl-33773155

RESUMO

BACKGROUND: Phthalates, which are used as excipients of drugs, have been related to adverse reproductive outcomes. However, the relationships between medication use and phthalate exposure among women undergoing in vitro fertilization (IVF) have not been studied. OBJECTIVE: To investigate the associations between the medication intake and phthalate metabolites in urine and follicular fluid (FF). METHOD: Eight phthalate metabolites were measured in urine and FF samples from 274 women undergoing IVF using liquid chromatography-tandem mass spectrometry. Information on recent medication intake was obtained via interview by trained staff. We constructed generalized linear regression models to examine the associations of medication intake with phthalate metabolite concentrations and dose-response relationships between the number of medicines used and metabolite concentrations in two matrices. RESULTS: Four of 10 drugs were used by more than 10% of the participants, including vitamins (23.0%), traditional Chinese medicine (TCM, 22.3%), antioxidants (12.4%) and amoxicillin (10.2%). Participants who had used TCM had 26.0% (95% CI: 0.0, 58.8%), 32.6% (95% CI: 4.2, 68.8%) and 32.3% (95% CI: 2.6, 70.6%) higher urinary mono-n-butyl phthalate (MBP), mono(2-ethyl-5-hydroxyhexyl) phthalate (MEHHP) and mono(2-ethyl-5-oxohexyl) phthalate (MEOHP) concentrations, respectively, than those who had not. Antioxidant intake was associated with a 30.6% (95% CI: -48.5, -6.6%) decrease in the urinary MBP concentration. Compared with non-users, women who reported the use of medicines had 53.2% (95% CI: 2.7, 128.5%) higher concentrations of MMP and a 37.7% (95% CI: -60.7, -1.5%) lower level of MBP in FF, respectively. CONCLUSION: Our data suggest that the intake of some medications may increase phthalate exposure among women undergoing IVF.


Assuntos
Poluentes Ambientais/metabolismo , Líquido Folicular/metabolismo , Ácidos Ftálicos/metabolismo , Adulto , Antioxidantes/análise , Cromatografia Líquida , Exposição Ambiental/análise , Exposição Ambiental/estatística & dados numéricos , Poluentes Ambientais/análise , Poluentes Ambientais/urina , Feminino , Fertilização In Vitro , Líquido Folicular/química , Humanos , Espectrometria de Massas , Pessoa de Meia-Idade , Ácidos Ftálicos/urina , Reprodução , Vitamina A , Vitaminas , Adulto Jovem
2.
Artigo em Inglês | MEDLINE | ID: mdl-33563085

RESUMO

The objective of this study was to investigate 13 phthalic acid esters (PAEs) with medium or long straight-alkyl-chain, branching or unsaturated side chains, because their structural characteristics make them difficult to biodegrade or highly toxic. A biodegradability and biotoxicity multi-effect pharmacophore model was built using comprehensive evaluation method. The results suggested that introducing hydrophobic groups to the side chains of the PAEs could improve the molecules' biodegradability and biotoxicity effects simultaneously. Thus, 40 target PAE (HEHP, DNOP, DUP) derivatives were designed. Two environmentally friendly PAE derivatives (HEHP-Anthryl and HEHP-Naphthyl) were screened via the test of environmental friendliness and functionality. In addition, the biodegradation and biotoxicity of derivatives were found to have improved as a result of the change in van der Waals forces between molecules and their corresponding proteins. Moreover, the environmental safety of the screened PAE derivatives was confirmed by predicting the toxicity of their intermediates and calculating the energy barrier values for biodegradation and metabolic pathways. This study could provide theoretical guidance for the practical development of environmentally friendly plasticizer.


Assuntos
Ésteres , Modelos Teóricos , Ácidos Ftálicos , Plastificantes , Animais , Biodegradação Ambiental , Decápodes/efeitos dos fármacos , Ésteres/química , Ésteres/metabolismo , Ésteres/toxicidade , Interações Hidrofóbicas e Hidrofílicas , Ácidos Ftálicos/química , Ácidos Ftálicos/metabolismo , Ácidos Ftálicos/toxicidade , Plastificantes/química , Plastificantes/metabolismo , Plastificantes/toxicidade
3.
Ecotoxicol Environ Saf ; 208: 111633, 2021 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-33396153

RESUMO

Exposure to phthalates poses potential to damage multiple organs and system in the body. However, limited data are available regarding effects of seasonal exposure levels of phthalates and indicators reflecting inflammatory response. We designed a pilot study with repeated measures. We recruited 106 eligible habitants from Wuhan city, China. They completed questionnaires, physical examinations and provided urine specimens in winter and summer seasons. We found that urinary levels of low-molecular-weight phthalate metabolites were higher in summer than in winter (all P < 0.01). In winter, an interquartile range increase (1.264 µg/L) in 3-day moving average of high-molecular-weight phthalate metabolites corresponded to a 13.634% (95% CI: -22.331, -3.941) decrease in mean platelet volume, 25.879% (95% CI: -37.424, -12.204) for lymphocyte count or 10.862% (95% CI: -18.716, -2.125) for platelet count (P < 0.05 or P < 0.01). However, in summer, an interquartile range increase (1.215 µg/L) in urinary levels of high-molecular-weight phthalate metabolites corresponded to an 8.743% (95% CI: 4.217, 13.467) increase in platelet distribution width value or a 4.597% (95% CI: 2.335, 6.780) for mean platelet volume value at 3-day lag (both P < 0.01). In conclusion, phthalate exposure exhibited the potential for the activation of platelet function, particularly in winter. Seasonal variations of phthalate exposure should be considered when assessing health risk.


Assuntos
Exposição Ambiental/efeitos adversos , Poluentes Ambientais/efeitos adversos , Inflamação/etiologia , Ácidos Ftálicos/efeitos adversos , China , Exposição Ambiental/análise , Poluentes Ambientais/metabolismo , Poluentes Ambientais/urina , Feminino , Humanos , Inflamação/sangue , Masculino , Ácidos Ftálicos/metabolismo , Ácidos Ftálicos/urina , Projetos Piloto , Projetos de Pesquisa , Medição de Risco , Estações do Ano
4.
Ecotoxicol Environ Saf ; 209: 111795, 2021 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-33341696

RESUMO

Our previous work has reported that EstJ6 was a phthalate-degrading hydrolase. In the study, a random mutant library was constructed by two rounds of error-prone PCR, three mutants (ET1.1, ET2.1, and ET2.2) with enhanced hydrolytic activity against dibutyl phthalate (DBP) were obtained. The best mutant ET2.2, accumulated three amino acid substitutions (Thr91Met, Ala67Val, and Val249Ile) and exhibited 2.8-fold increase enzyme activity and 2.3-fold higher expression level. Meanwhile, compared with EstJ6, ET2.2 showed over 50% improvement in thermostability (at 50 °C for 1 h) and 1.2-fold increase in 50% methanol tolerance. Kinetic parameters analysis revealed that the Km value for ET2.2 decreased by 60% and the kcat/Km value increased by 166%. The molecular docking indicated that the shortening of hydrogen bond between Ser146-OH and DBP-CO, which may led to an increase in enzyme activity and catalytic efficiency, the enhancement of hydrophobicity of hydrophobic pocket was related to the improvement of organic solvents tolerance, and three hydrophobic amino acid substitutions Thr91Met, Ala67Val, and Val249Ile facilitated to improve the thermal stability and organic solvents tolerance. These results confirmed that random mutagenesis was an effective tool for improving enzyme properties and lay a foundation for practical applications of phthalate-degrading hydrolase in biotechnology and industrial fields.


Assuntos
Hidrolases/metabolismo , Ácidos Ftálicos/metabolismo , Catálise , Dibutilftalato , Estabilidade Enzimática , Biblioteca Gênica , Hidrólise , Cinética , Metanol/metabolismo , Simulação de Acoplamento Molecular , Mutagênese , Solventes
5.
Food Chem ; 336: 127722, 2021 Jan 30.
Artigo em Inglês | MEDLINE | ID: mdl-32771902

RESUMO

In this article we describe a new and simple analytical method based on the Quick, Easy, Cheap, Effective, Rugged and Safe technique followed by dispersive solid-phase extraction clean-up with C18 and Lipifiltr® and LC-HRMS for simultaneously extracting six phthalate diesters and six of their metabolites (phthalate monoesters) from highly consumed seafood species. The method was validated for seafood with high and low lipid contents. Apparent recoveries were up to 79% for all compounds. Matrix effect values ranged from -8 to -48% for all compounds in both types of matrices. Method limits of detection were 1-25 ng g-1 dry weight (d.w.) for most compounds. Five seafood species were analysed using this method, and several phthalate diesters and monoesters were successfully quantified. Phthalate diesters were found at concentrations of up to 982 ng g-1 (d.w.) and phthalate monoesters were found at concentrations of up to 178 ng g-1 (d.w.).


Assuntos
Espectrometria de Massas/métodos , Ácidos Ftálicos/análise , Alimentos Marinhos/análise , Cromatografia Líquida de Alta Pressão , Ésteres/química , Limite de Detecção , Ácidos Ftálicos/isolamento & purificação , Ácidos Ftálicos/metabolismo , Extração em Fase Sólida
6.
Environ Sci Technol ; 54(16): 10181-10190, 2020 08 18.
Artigo em Inglês | MEDLINE | ID: mdl-32678582

RESUMO

Numerous studies focused on the human exposure to plasticizers via dermal contact; however, the percutaneous penetration of plasticizers was seldom considered in exposure assessment. In the present study, skin wipes of palms, back-of-hands, and forehead were collected from 114 participants (ages: 18-27). There was no significant difference between the levels of phthalates from palms and back-of-hand, while all phthalates collected from the forehead were significantly higher than those from palms and back-of-hand (p < 0.001); di(2-ethylhexyl)phthalate levels were substantially higher than other detected phthalates followed by di(n-butyl)phthalate and di(isobutyl)phthalate (DiBP), and for alternative plasticizers, bis-2-ethylhexyl terephthalate levels were substantially higher than acetyltributyl citrate and bis-2-ethylhexyladipate. Skin permeation and metabolism of phthalates was assessed using human skin equivalent models. The permeability coefficient (kp) values of phthalates were significantly negatively correlated with their log octanol-water partition coefficient (log Kow), while a significantly positive correlation was found between the log Kow and the cumulative amounts of phthalates in the cells. The proportion of phthalate intake via dermal exposure to skin wipes ranges from 1.3% (for dimethyl phthalate) to 8.6% (for DiBP) and suggests that dermal absorption is a significant route for adult phthalate exposure.


Assuntos
Ácidos Ftálicos , Plastificantes , Adolescente , Adulto , Dibutilftalato/metabolismo , Exposição Ambiental/análise , Humanos , Ácidos Ftálicos/metabolismo , Pele/química , Absorção Cutânea , Adulto Jovem
7.
Chemosphere ; 255: 127034, 2020 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-32679634

RESUMO

Due to the increasing presence of plastic and plastic associated contaminants in the aquatic environments, the monitoring of this contamination in fish products and the understanding of possible human health implications is considered urgent. However, data are still relatively scarce, mostly due to the methodological challenges in the chemical analysis: these contaminants are ubiquitous and procedural contamination from the laboratory is frequent. In this work, we compared solid-phase microextraction (SPME) to ultrasonic assisted solvent extraction (UASE) as sample preparation methods for the liquid chromatography coupled to tandem mass spectrometry (LC-MS/MS) determination of phthalates in fish fillets. UASE was carried out with an acetone-hexane (1:1) solution and according to a reference procedure aimed to obtain the exhaustive extraction of the target analytes. SPME was carried out by applying C18 fibers in direct immersion mode and by using water/methanol 20:80 mixture to desorb the aliquot required for the analysis. Overall, SPME displayed an improved control of the background contamination and enabled lower LOQs. Precision, calculated as relative standard deviation (RSD) on replicates of a reference sample, was below 24% for both the method. Analysis of real samples purchased from Italian supermarkets showed that SPME might be an efficient tool for estimating the risk associated with fish consumption.


Assuntos
Peixes/metabolismo , Ácidos Ftálicos/metabolismo , Poluentes Químicos da Água/metabolismo , Animais , Cromatografia Líquida/métodos , Microextração em Fase Sólida/métodos , Solventes/química , Espectrometria de Massas em Tandem/métodos , Ultrassom
8.
Nature ; 580(7802): 216-219, 2020 04.
Artigo em Inglês | MEDLINE | ID: mdl-32269349

RESUMO

Present estimates suggest that of the 359 million tons of plastics produced annually worldwide1, 150-200 million tons accumulate in landfill or in the natural environment2. Poly(ethylene terephthalate) (PET) is the most abundant polyester plastic, with almost 70 million tons manufactured annually worldwide for use in textiles and packaging3. The main recycling process for PET, via thermomechanical means, results in a loss of mechanical properties4. Consequently, de novo synthesis is preferred and PET waste continues to accumulate. With a high ratio of aromatic terephthalate units-which reduce chain mobility-PET is a polyester that is extremely difficult to hydrolyse5. Several PET hydrolase enzymes have been reported, but show limited productivity6,7. Here we describe an improved PET hydrolase that ultimately achieves, over 10 hours, a minimum of 90 per cent PET depolymerization into monomers, with a productivity of 16.7 grams of terephthalate per litre per hour (200 grams per kilogram of PET suspension, with an enzyme concentration of 3 milligrams per gram of PET). This highly efficient, optimized enzyme outperforms all PET hydrolases reported so far, including an enzyme8,9 from the bacterium Ideonella sakaiensis strain 201-F6 (even assisted by a secondary enzyme10) and related improved variants11-14 that have attracted recent interest. We also show that biologically recycled PET exhibiting the same properties as petrochemical PET can be produced from enzymatically depolymerized PET waste, before being processed into bottles, thereby contributing towards the concept of a circular PET economy.


Assuntos
Hidrolases/química , Hidrolases/metabolismo , Plásticos/química , Plásticos/metabolismo , Polietilenotereftalatos/química , Polietilenotereftalatos/metabolismo , Engenharia de Proteínas , Reciclagem , Actinobacteria/enzimologia , Burkholderiales/enzimologia , Hidrolases de Éster Carboxílico/química , Hidrolases de Éster Carboxílico/metabolismo , Dissulfetos/química , Dissulfetos/metabolismo , Ensaios Enzimáticos , Estabilidade Enzimática , Fusarium/enzimologia , Modelos Moleculares , Ácidos Ftálicos/metabolismo , Polimerização
9.
Microb Cell Fact ; 19(1): 77, 2020 Mar 24.
Artigo em Inglês | MEDLINE | ID: mdl-32209105

RESUMO

BACKGROUND: Microbes are rich sources of enzymes and esterases are one of the most important classes of enzymes because of their potential for application in the field of food, agriculture, pharmaceuticals and bioremediation. Due to limitations in their cultivation, only a small fraction of the complex microbial communities can be cultured from natural habitats. Thus to explore the catalytic potential of uncultured organisms, the metagenomic approach has turned out to be an effective alternative method for direct mining of enzymes of interest. Based on activity-based screening method, an esterase-positive clone was obtained from metagenomic libraries. RESULTS: Functional screening of a soil metagenomic fosmid library, followed by transposon mutagenesis led to the identification of a 1179 bp esterase gene, estM2, that encodes a 392 amino acids long protein (EstM2) with a translated molecular weight of 43.12 kDa. Overproduction, purification and biochemical characterization of the recombinant protein demonstrated carboxylesterase activity towards short-chain fatty acyl esters with optimal activity for p-nitrophenyl butyrate at pH 8.0 and 37 °C. Amino acid sequence analysis and subsequent phylogenetic analysis suggested that EstM2 belongs to the family VIII esterases that bear modest similarities to class C ß-lactamases. EstM2 possessed the conserved S-x-x-K motif of class C ß-lactamases but did not exhibit ß-lactamase activity. Guided by molecular docking analysis, EstM2 was shown to hydrolyze a wide range of di- and monoesters of alkyl-, aryl- and benzyl-substituted phthalates. Thus, EstM2 displays an atypical hydrolytic potential of biotechnological significance within family VIII esterases. CONCLUSIONS: This study has led to the discovery of a new member of family VIII esterases. To the best of our knowledge, this is the first phthalate hydrolase (EstM2), isolated from a soil metagenomic library that belongs to a family possessing ß-lactamase like catalytic triad. Based on its catalytic potential towards hydrolysis of both phthalate diesters and phthalate monoesters, this enzyme may find use to counter the growing pollution caused by phthalate-based plasticizers in diverse geological environment and in other aspects of biotechnological applications.


Assuntos
Esterases/genética , Metagenoma/genética , Ácidos Ftálicos/metabolismo
10.
Chemosphere ; 249: 126457, 2020 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-32220682

RESUMO

In this study, we investigated the accumulation and transport patterns of six phthalic acid esters (PAEs) in two leafy vegetables under hydroponic conditions. The tested PAEs included dibutyl phthalate (DBP), diethyl phthalate (DEP), diallyl phthalate (DAP), diisobutyl phthalate (DIBP), dimethyl phthalate (DMP) and benzyl butyl phthalate (BBP), and the tested vegetables included Gaogengbai and Ziyoucai. The results revealed that the six PAEs were taken up by vegetables from the solution, although their accumulation and distribution varied among PAEs. The ability of concentrating PAEs into the roots followed the order of BBP > DBP > DIBP > DAP > DEP > DMP, whereas the ability of concentrating PAEs in plant shoots had the opposite order. By analysing the fractionation of the six PAEs in vegetable roots, DMP had the largest proportion in terms of apoplastic movement, while BBP had the largest proportion in terms of symplastic movement. Correlation analyses revealed that the differences among the accumulation and distribution behaviours of the six PAEs in plant tissues were not only related to their physicochemical parameters, such as alkyl chain length and the octanol/water partition coefficient (logKow), but also related to the proportion of apoplastic and symplastic movement in the plant roots. In addition, PAEs were more readily accumulated in the Gaogengbai roots than in the Ziyoucai roots; however, the opposite trend was observed for the shoots.


Assuntos
Ácidos Ftálicos/metabolismo , Poluentes do Solo/metabolismo , Verduras/metabolismo , Dibutilftalato/análogos & derivados , Ésteres/análise , Hidroponia , Ácidos Ftálicos/análise , Poluentes do Solo/análise , Verduras/química
11.
Appl Environ Microbiol ; 86(11)2020 05 19.
Artigo em Inglês | MEDLINE | ID: mdl-32220846

RESUMO

The degradation of the xenobiotic phthalic acid esters by microorganisms is initiated by the hydrolysis to the respective alcohols and ortho-phthalate (hereafter, phthalate). In aerobic bacteria and fungi, oxygenases are involved in the conversion of phthalate to protocatechuate, the substrate for ring-cleaving dioxygenases. In contrast, anaerobic bacteria activate phthalate to the extremely unstable phthaloyl-coenzyme A (CoA), which is decarboxylated by oxygen-sensitive UbiD-like phthaloyl-CoA decarboxylase (PCD) to the central benzoyl-CoA intermediate. Here, we demonstrate that the facultatively anaerobic, denitrifying Thauera chlorobenzoica 3CB-1 and Aromatoleum evansii KB740 strains use phthalate as a growth substrate under aerobic and denitrifying conditions. In vitro assays with extracts from cells grown aerobically with phthalate demonstrated the succinyl-CoA-dependent activation of phthalate followed by decarboxylation to benzoyl-CoA. In T. chlorobenzoica 3CB-1, we identified PCD as a highly abundant enzyme in both aerobically and anaerobically grown cells, whereas genes for phthalate dioxygenases are missing in the genome. PCD was highly enriched from aerobically grown T. chlorobenzoica cells and was identified as an identical enzyme produced under denitrifying conditions. These results indicate that the initial steps of aerobic phthalate degradation in denitrifying bacteria are accomplished by the anaerobic enzyme inventory, whereas the benzoyl-CoA oxygenase-dependent pathway is used for further conversion to central intermediates. Such a hybrid pathway requires intracellular oxygen homeostasis at concentrations low enough to prevent PCD inactivation but sufficiently high to supply benzoyl-CoA oxygenase with its cosubstrate.IMPORTANCE Phthalic acid esters (PAEs) are industrially produced on a million-ton scale per year and are predominantly used as plasticizers. They are classified as environmentally relevant xenobiotics with a number of adverse health effects, including endocrine-disrupting activity. Biodegradation by microorganisms is considered the most effective process to eliminate PAEs from the environment. It is usually initiated by the hydrolysis of PAEs to alcohols and o-phthalic acid. Degradation of o-phthalic acid fundamentally differs in aerobic and anaerobic microorganisms; aerobic phthalate degradation heavily depends on dioxygenase-dependent reactions, whereas anaerobic degradation employs the oxygen-sensitive key enzyme phthaloyl-CoA decarboxylase. We demonstrate that aerobic phthalate degradation in facultatively anaerobic bacteria proceeds via a previously unknown hybrid degradation pathway involving oxygen-sensitive and oxygen-dependent key enzymes. Such a strategy is essential for facultatively anaerobic bacteria that frequently switch between oxic and anoxic environments.


Assuntos
Proteínas de Bactérias/metabolismo , Desnitrificação , Ácidos Ftálicos/metabolismo , Rhodocyclaceae/metabolismo , Aerobiose , Bactérias/metabolismo , Rhodocyclaceae/enzimologia , Thauera/enzimologia , Thauera/metabolismo
12.
Environ Health Perspect ; 128(2): 27004, 2020 02.
Artigo em Inglês | MEDLINE | ID: mdl-32073305

RESUMO

BACKGROUND: The etiology of autism spectrum disorder is poorly understood. Few studies have investigated the link between endocrine-disrupting chemicals and autistic traits. We examined the relationship between gestational phthalates and autistic traits in 3- to 4-y-old Canadian children. We also investigated potential effect modification by sex and folic acid supplementation. METHODS: We enrolled 2,001 women>18 years of age during the first trimester of pregnancy between 2008 and 2011 from 10 cities in Canada. At 3-4 years of age, 610 children underwent neuropsychological assessments including the Social Responsiveness Scale-II (SRS-2) as a measure of autistic traits and social impairment. We measured 11 phthalate metabolites in maternal first trimester urine samples and assessed folic acid supplementation from reported intakes. We estimated covariate-adjusted differences in SRS-2 T-scores with a doubling in phthalate concentrations in 510 children with complete data. RESULTS: Mean total SRS T-score was 45.3 (SD=6.1). Children with higher gestational exposure to mono-n-butyl (MBP) and mono-3-carboxypropyl (MCPP) concentrations exhibited significantly higher total SRS T-scores, indicating greater overall social impairment, as well as higher scores on subdomains, indicating deficits in social cognition, social communication, social motivation, and restricted interests/repetitive behaviors. A doubling in MBP or MCPP concentrations was associated with 0.6 (95% CI: 0.1, 1.0) and 0.5 (95% CI: 0.1, 0.8) higher total SRS T-scores. Associations were consistently and significantly stronger in boys (ßMBP=1.0; 95% CI: 0.4, 1.6; n=252) compared with girls (ßMBP=0.1; 95% CI: -0.6, 0.7; n=258) and among children who had lower prenatal folic acid supplementation (<400µg/d) (ßMBP=1.3; 95% CI: 0.4, 2.3; n=59) compared with those who had adequate folic acid supplementation (≥400µg/d) (ßMBP=0.4; 95% CI: -0.1, 0.8; n=451). CONCLUSIONS: Higher gestational concentrations of some phthalate metabolites were associated with higher scores of autistic traits as measured by the SRS-2 in boys, but not girls; these small size effects were mitigated by first trimester-of-pregnancy folic acid supplementation. https://doi.org/10.1289/EHP5621.


Assuntos
Transtorno do Espectro Autista/epidemiologia , Poluentes Ambientais/toxicidade , Ácido Fólico/metabolismo , Ácidos Ftálicos/toxicidade , Efeitos Tardios da Exposição Pré-Natal/epidemiologia , Adulto , Canadá/epidemiologia , Criança , Pré-Escolar , Poluentes Ambientais/metabolismo , Feminino , Humanos , Masculino , Exposição Materna/estatística & dados numéricos , Ácidos Ftálicos/metabolismo , Gravidez
13.
Chemosphere ; 249: 126149, 2020 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-32062213

RESUMO

The toxicity of endocrine disruptors depends on the synergistic interactions of biological, environmental, and behavioral factors. The specific effects of diet, consumer product use, and behaviors, however, are debated in the literature, particularly with regard to endocrine disruptors found in breast milk. This study aimed to measure the levels of phthalate metabolites, bisphenol A, parabens, and triclosan in breast milk and to investigate their associations with various lifestyle factors. The breast milk samples as well as surveys were collected from 221 first-time mothers throughout South Korea and each sample was analyzed for the presence of 15 endocrine disruptors. Phthalate metabolites were detected in 5.4-83.3% of the samples, with median concentrations of 0.08-1.72 µg/L, while bisphenol A, parabens, and triclosan were detected in 25.8-88.2% of the samples, with median concentrations of 0.12-1.47 µg/L. High levels of endocrine disruptors were associated with frequent consumption of fish and cup noodles; the use of plastic and disposable food containers; the use of air fresheners, lotions and make-up; the purchase of new furniture; and socioeconomic status. We also observed the potential role of moderate walking activity on the reduction of these chemicals in breast milk. Our data provide evidence of the potential effects of diet, consumer products, and behavior on the presence of phthalate metabolites, bisphenol A, parabens, and triclosan in breast milk. Future studies should include community or regional impact on a mothers' exposure to endocrine disruptors, to assess the joint contribution of both individual and neighborhood factors.


Assuntos
Compostos Benzidrílicos/metabolismo , Poluentes Ambientais/metabolismo , Exposição Materna/estatística & dados numéricos , Leite Humano/metabolismo , Parabenos/metabolismo , Fenóis/metabolismo , Ácidos Ftálicos/metabolismo , Triclosan/metabolismo , Dieta , Disruptores Endócrinos , Feminino , Humanos , Estilo de Vida , Leite Humano/química , Mães , Parabenos/análise , República da Coreia , Inquéritos e Questionários
14.
J Toxicol Environ Health A ; 83(2): 66-81, 2020 01 17.
Artigo em Inglês | MEDLINE | ID: mdl-32077375

RESUMO

Bisphenol A (BPA) and phthalate diesters are ubiquitous environmental contaminants. While these compounds have been reported as reproductive toxicants, their effects may partially be attributed to metabolites. The aim of this study was to examine reproductive organ development in chicken embryos exposed to the BPA metabolite, 4-methyl-2,4-bis(4-hydroxyphenyl)pent-1-ene (MBP; 100 µg/g egg) or a human-relevant mixture of 4 phthalate monoesters (85 µg/g egg). The mixture was designed within the EU project EDC-MixRisk based upon a negative association with anogenital distance in boys at 21 months of age in a Swedish pregnancy cohort. Chicken embryos were exposed in ovo from an initial stage of gonad differentiation (embryonic day 4) and dissected two days prior to anticipated hatching (embryonic day 19). No discernible effects were noted on reproductive organs in embryos exposed to the mixture. MBP-treated males exhibited retention of Müllerian ducts and feminization of the left testicle, while MBP-administered females displayed a diminished the left ovary. In the left testicle of MBP-treated males, mRNA expression of female-associated genes was upregulated while the testicular marker gene SOX9 was downregulated, corroborating a feminizing effect by MBP. Our results demonstrate that MBP, but not the phthalate monoester mixture, disrupts both male and female reproductive organ development in an avian embryo model.


Assuntos
Compostos Benzidrílicos/metabolismo , Compostos Benzidrílicos/toxicidade , Fenóis/metabolismo , Fenóis/toxicidade , Ácidos Ftálicos/química , Processos de Determinação Sexual/efeitos dos fármacos , Animais , Compostos Benzidrílicos/química , Embrião de Galinha , Feminino , Regulação da Expressão Gênica no Desenvolvimento/efeitos dos fármacos , Humanos , Masculino , Ductos Paramesonéfricos/efeitos dos fármacos , Ductos Paramesonéfricos/embriologia , Ovário/efeitos dos fármacos , Ovário/embriologia , Fenóis/química , Ácidos Ftálicos/metabolismo , RNA Mensageiro/genética , RNA Mensageiro/metabolismo , Testículo/efeitos dos fármacos , Testículo/embriologia
15.
Environ Int ; 137: 105525, 2020 04.
Artigo em Inglês | MEDLINE | ID: mdl-32028175

RESUMO

The exposure of marine mammals to phthalates has received considerable attention due to the ubiquitous occurrence of these pollutants in the marine environment and their potential adverse health effects. The occurrence of phthalate metabolites is well established in human populations, but data is scarce for marine mammals. In this study, concentrations of 17 phthalate metabolites were determined in liver samples collected from one hundred (n = 100) by-caught harbor porpoises (Phocoena phocoena) along the coast of Norway. Overall, thirteen phthalate metabolites were detected in the samples. Monoethyl phthalate (mEP), mono-iso-butyl phthalate (mIBP), mono-n-butyl phthalate (mBP) and phthalic acid (PA) were the most abundant metabolites, accounting for detection rates ≥ 85%. The highest median concentrations were found for mIBP (30.6 ng/g wet weight [w.w.]) and mBP (25.2 ng/g w.w.) followed by PA (7.75 ng/g w.w.) and mEP (5.67 ng/g w.w.). The sum of the median phthalate metabolites concentrations that were found in the majority of samples (detection rates > 50%) indicated that concentrations were lower for porpoises collected along the coastal area of Bodø (Nordland), Lebesby (Finnmark) and Varangerfjord (as compared to other coastal areas); these areas are among the least populated coastal areas but also the most distant (>700 km) from offshore active oil and gas fields. The monomethyl phthalate metabolite (mMP) was detected in 69% of the samples, and to our knowledge, alongside with PA, this is the first report of their occurrence in marine mammals. PA, as the non-specific marker of phthalate exposures, showed a statistically significant negative association with the body mass and length of the harbor porpoises. Among the phthalate metabolites, statistically significant positive associations were found between mBP and mIBP, mMP and mEP, PA and mEP, mIBP and mono(2-ethyl-5-oxohexyl) phthalate (mEOHP), mIBP and mono(2-ethyl-5-hydroxyhexyl) phthalate (mEHHP), mBP and mEHHP, mono-n-nonyl phthalate (mNP) and PA, and between monobenzyl phthalate (mBzP) and mNP. To our knowledge, this is the first study on the biomonitoring of 17 phthalate metabolites in harbor porpoises.


Assuntos
Poluentes Ambientais , Phocoena , Ácidos Ftálicos , Animais , Exposição Ambiental , Humanos , Noruega , Ácidos Ftálicos/metabolismo
16.
Microbes Environ ; 35(1)2020.
Artigo em Inglês | MEDLINE | ID: mdl-32101840

RESUMO

The genome of Streptomyces scabies, the predominant causal agent of potato common scab, encodes a potential cutinase, the protein Sub1, which was previously shown to be specifically induced in the presence of suberin. The sub1 gene was expressed in Escherichia coli and the recombinant protein Sub1 was purified and characterized. The enzyme was shown to be versatile because it hydrolyzes a number of natural and synthetic substrates. Sub1 hydrolyzed p-nitrophenyl esters, with the hydrolysis of those harboring short carbon chains being the most effective. The Vmax and Km values of Sub1 for p-nitrophenyl butyrate were 2.36 mol g-1 min-1 and 5.7 10-4 M, respectively. Sub1 hydrolyzed the recalcitrant polymers cutin and suberin because the release of fatty acids from these substrates was observed following the incubation of the enzyme with these polymers. Furthermore, the hydrolyzing activity of the esterase Sub1 on the synthetic polymer polyethylene terephthalate (PET) was demonstrated by the release of terephthalic acid (TA). Sub1 activity on PET was markedly enhanced by the addition of Triton and was shown to be stable at 37°C for at least 20 d.


Assuntos
Proteínas de Bactérias/metabolismo , Hidrolases de Éster Carboxílico/metabolismo , Doenças das Plantas/microbiologia , Polímeros/metabolismo , Streptomyces/enzimologia , Proteínas de Bactérias/genética , Proteínas de Bactérias/isolamento & purificação , Hidrolases de Éster Carboxílico/genética , Hidrolases de Éster Carboxílico/isolamento & purificação , Ácidos Graxos/metabolismo , Hidrólise , Ácidos Ftálicos/metabolismo , Proteínas Recombinantes/genética , Proteínas Recombinantes/isolamento & purificação , Proteínas Recombinantes/metabolismo , Solanum tuberosum/microbiologia , Streptomyces/genética
17.
J Pharm Biomed Anal ; 181: 113092, 2020 Mar 20.
Artigo em Inglês | MEDLINE | ID: mdl-31915107

RESUMO

Phthalates are commonly used as plasticizers and are known as risk factors toward several conditions such as cancer, birth defects, and endocrine disruption. Biomonitoring of phthalates is necessary to assess the potentially harmful effects of long-term exposure. In this work, we have developed a novel QuEChERS method to determine eight phthalate metabolites-mono-(3-carboxypropyl) phthalate, mono-(2-ethyl-5-carboxypentyl) phthalate, mono-(2-ethyl-5-hydroxyhexyl) phthalate, mono-(2-ethyl-5-oxohexyl) phthalate, mono-n-butyl phthalate, mono-benzyl phthalate, mono-(carboxyloctyl) phthalate, and mono-(carboxynonyl) phthalate-in human milk. The extraction process was optimized by comparing three different QuEChERS methods, and a further purification step was used to eliminate interferential lipid. In this process, several factors, such as the pH based on QuEChERS additive salts, acid dissociation constant, and distribution coefficient of the analyte, were found to have a significant effect on the extraction efficiency of the QuEChERS method. Target compounds were determined using liquid chromatography-tandem mass spectrometry equipped with electrospray ionization in the multiple-reaction monitoring mode. The developed method was verified by evaluating the selectivity, linearity, lower limit of quantification, accuracy, precision, and recovery, and applied to monitor real milk samples from 26 people. It is expected that the established method can be utilized not only to monitor phthalate metabolites in biological samples but also to identify the correlation between phthalate concentrations observed for the mother and the newborn.


Assuntos
Poluentes Ambientais/isolamento & purificação , Extração Líquido-Líquido/métodos , Leite Humano/química , Ácidos Ftálicos/isolamento & purificação , Plastificantes/isolamento & purificação , Cromatografia Líquida de Alta Pressão/métodos , Poluentes Ambientais/metabolismo , Feminino , Humanos , Ácidos Ftálicos/metabolismo , Plastificantes/metabolismo , Espectrometria de Massas em Tandem/métodos
18.
Environ Pollut ; 260: 114005, 2020 May.
Artigo em Inglês | MEDLINE | ID: mdl-31995769

RESUMO

Phthalates are widely used as binders and plasticizers in industrial and consumer products but show diverse toxicity. We investigated the level of human exposure to phthalates in Beijing, one of the most densely populated cities in the world. In this study, 12 metabolites of phthalates were measured in 70 spot urine samples collected from Beijing residents from August 2017 to April 2018 using ultra high-performance liquid chromatography tandem mass spectrometry. We found that metabolites of phthalates were ubiquitous in all urine samples. Total concentrations of phthalate metabolites ranged from 39.6 to 1931 ng mL-1, with median concentrations were in decreasing order of children (371 ng mL-1)> younger adults (332 ng mL-1)> older adults (276 ng mL-1). Mono-n-butyl phthalate (MnBP) was the predominant compound, and occurred at concentrations greater than those reported for people in other countries. The mean values of estimated daily intakes (EDIs) of ∑phthalate were 35.2, 10.3 and 10.9 ng (kg-bm)-1 d-1 for children, younger adults and older adults, respectively. EDIs of di-n-butyl phthalate (DnBP), di-iso-butyl phthalate (DiBP) and di-(2-ethylhexyl) phthalate (DEHP) exceeded reference values suggested by the US Environmental Protection Agency and the European Food Safety Authority. When concentrations were normalized to volume or creatinine-adjusted, hazard quotients (HQs) for 40 of 70 participants exhibited larger HQs >1 for individual phthalates, which was indicative of potential for adverse effects. Thus, exposure to phthalates might be a critical factor contributing to adverse health effects in Beijing residents. To the best of our knowledge, this is the first study to establish a pre-baseline level of urinary phthalate metabolites among residents in Beijing.


Assuntos
Exposição Ambiental/estatística & dados numéricos , Poluentes Ambientais , Ácidos Ftálicos/metabolismo , Idoso , Pequim , Criança , China , Cidades , Dibutilftalato , Humanos
19.
Ecotoxicol Environ Saf ; 190: 110148, 2020 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-31911388

RESUMO

Phthalate esters have raised public concerns owing to their effects on the environment and human health. We identified a novel phthalate-degrading hydrolase, EstJ6, from a metagenomic library using function-driven screening. Phylogenetic analysis indicated that EstJ6 is a member of family IV esterases. EstJ6 hydrolyzed various dialkyl and monoalkyl phthalate esters, and exhibited high hydrolytic activity (128 U/mg) toward dibutyl phthalate at 40 °C and pH 7.5. EstJ6 hydrolyzed not only common phthalate esters with simple side chains but also diethylhexyl phthalate and monoethylhexyl phthalate, which have complex and long side chains. Site-directed mutagenesis indicated that the catalytic triad residues of EstJ6 consists of Ser146, Glu240, and His270. EstJ6 is therefore a promising biodegradation enzyme, and our study illustrates the advantages of a metagenomic approach in identifying enzyme-coding genes for agricultural, food, and biotechnological applications.


Assuntos
Biodegradação Ambiental , Hidrolases/metabolismo , Ácidos Ftálicos/metabolismo , Dibutilftalato/metabolismo , Dietilexilftalato/metabolismo , Esterases/metabolismo , Ésteres/química , Biblioteca Gênica , Hidrolases/genética , Hidrólise , Metagenoma , Filogenia , Solo
20.
Chemosphere ; 246: 125808, 2020 May.
Artigo em Inglês | MEDLINE | ID: mdl-31918107

RESUMO

This study evaluated the acute developmental toxicity of six priority phthalic acid esters (PAEs) including dimethyl phthalate (DMP), diethyl phthalate (DEP), dibutyl phthalate (DBP), di-2-ethylhexyl phthalate (DEHP), di-n-octyl phthalate (DNOP), and benzyl butyl phthalate (BBP) in zebrafish embryos. A novel alcian blue and alizarin red double staining was performed to detect skeletal development of zebrafish larvae. Results revealed that all six PAEs could induce different developmental abnormalities in zebrafish larvae, including abnormal movement, decreased heart rate, spinal curvature, and pericardial edema. The bone development of zebrafish larvae exposed to PAEs was also affected by PAEs acute exposure. Among PAEs, DBP, and BBP even at low doses can cause mortality in zebrafish, implying their higher toxicity. Contrarily, DEHP and DNOP showed minor effects on the developmental morphology of zebrafish larvae. However, the gene expression levels of skeleton-related genes showed the upregulation of the runx2b and shha genes after DEHP and DBP exposure. Taken together, the strict use and release of PAEs in the environment should be supervised by the government for ecological and environmental safety.


Assuntos
Morfogênese/efeitos dos fármacos , Ácidos Ftálicos/toxicidade , Esqueleto/crescimento & desenvolvimento , Poluentes Químicos da Água/toxicidade , Animais , Dibutilftalato/toxicidade , Dietilexilftalato/toxicidade , Ésteres/toxicidade , Larva , Ácidos Ftálicos/metabolismo , Esqueleto/efeitos dos fármacos , Peixe-Zebra/fisiologia
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