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Environment International Oct 2023Environmental benzo(a)pyrene (BaP) and its ultimate metabolite BPDE (benzo(a)pyrene-7,8-dihydrodiol-9,10-epoxide) are universal and inevitable persistent organic...
Environmental benzo(a)pyrene (BaP) and its ultimate metabolite BPDE (benzo(a)pyrene-7,8-dihydrodiol-9,10-epoxide) are universal and inevitable persistent organic pollutants and endocrine disrupting chemicals. Angiogenesis in placental decidua plays a pivotal role in healthy pregnancy. Ferroptosis is a newly identified and iron-dependent cell death mode. However, till now, BaP/BPDE exposure, ferroptosis, defective angiogenesis, and miscarriage have never been correlated; and their regulatory mechanisms have been rarely explored. In this study, we used assays with BPDE-exposed HUVECs (human umbilical vein endothelial cells), decidual tissues and serum samples collected from unexplained recurrent miscarriage and their matched healthy control groups, and placental tissues of BaP-exposed mouse miscarriage model. We found that BaP/BPDE exposure caused ferroptosis and then directly suppressed angiogenesis and eventually induced miscarriage. In mechanism, BaP/BPDE exposure up-regulated free Fe level and promoted lipid peroxidation and also up-regulated MARCHF1 (a novel E3 ligase of GPX4) level to promote the ubiquitination degradation of GPX4, both of which resulted in HUVEC ferroptosis. Furthermore, we also found that GPX4 protein down-regulated the protein levels of VEGFA and ANG-1, two key proteins function for angiogenesis, and thus suppressed HUVEC angiogenesis. In turn, supplement with GPX4 could suppress ferroptosis, recover angiogenesis, and alleviate miscarriage. Moreover, the levels of free Fe and VEGFA in serum might predict the risk of miscarriage. Overall, this study uncovered the crosstalk among BaP/BPDE exposure, ferroptosis, angiogenesis, and miscarriage, discovering novel toxicological effects of BaP/BPDE on human reproductive health. This study also warned the public to avoid exposure to polycyclic aromatic hydrocarbons during pregnancy to effectively prevent adverse pregnancy outcomes.
Topics: Mice; Animals; Pregnancy; Humans; Female; 7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide; Ferroptosis; Abortion, Spontaneous; Benzo(a)pyrene; Endothelial Cells; Placenta; Proteins
PubMed: 37802009
DOI: 10.1016/j.envint.2023.108237 -
Photochemistry and Photobiology 2023Polycyclic aromatic hydrocarbons (PAHs) are a group of organic compounds derived mostly from the incomplete combustion of fossil fuels and biomass. Human skin can absorb...
Polycyclic aromatic hydrocarbons (PAHs) are a group of organic compounds derived mostly from the incomplete combustion of fossil fuels and biomass. Human skin can absorb PAHs and the uptake increases with their molar mass and lipophilicity. Benzopyrene is high molecular weight PAH frequently appearing in ambient pollution. It exists in two isomeric forms: benzo[a]pyrene (BaP) and benzo[e]pyrene (BeP), which exhibit different biological activity. Although certain properties of benzopyrenes suggested photoreactivity of the compounds, no direct measurements were previously conducted to characterize their photochemical activity. In this study, quantum yield and action spectra of singlet oxygen photogeneration by BaP and BeP were measured by time-resolved near-infrared phosphorescence, and the ability of both compounds to photogenerate superoxide anion was assessed by electron paramagnetic resonance (EPR) spin-trapping. The measurements revealed high efficiency of benzopyrenes to photogenerate singlet oxygen and their ability to photogenerate superoxide anion. Using HaCaT cells as single-layer skin model, we demonstrated concentration-dependent and light-dependent cytotoxicity of BaP and BeP. The compounds induced damage to the cell mitochondria and elevated the levels of intracellular reactive oxygen species.
Topics: Humans; Benzo(a)pyrene; Superoxides; Singlet Oxygen; Benzopyrenes; Keratinocytes; Polycyclic Aromatic Hydrocarbons
PubMed: 36117444
DOI: 10.1111/php.13721 -
Journal of the American Chemical Society Jun 2022Two belt-like expanded carbaporphyrins ( and ) were prepared via a one-pot procedure that involves a [6 + 3] condensation between a pyrene-bearing tetrapyrrole precursor...
Two belt-like expanded carbaporphyrins ( and ) were prepared via a one-pot procedure that involves a [6 + 3] condensation between a pyrene-bearing tetrapyrrole precursor () and pentafluorobenzaldehyde, followed by oxidation. Single crystal X-ray diffraction analyses revealed that and both contain six dipyrromethene moieties and three bridging pyrene units. In the structure of , there are two vertically orientated pyrene units and one transverse orientated pyrene unit; however, in all three pyrene units are vertically orientated. The structural differences between and are reflected in their respective physical properties as revealed by proton NMR, UV-vis, and fluorescence spectroscopies. In contrast to all-carbon nanobelts, and contain multiple pyrrolic nitrogen donors that could serve as potential metal coordination sites. As a test of this possibility, was used to prepare an unprecedented Zn complex containing 7 Zn metal centers connected by a network of bridging atoms, as confirmed by a single crystal X-ray diffraction analysis. To the best of our knowledge, this is the first example of a belt-like molecular system that can coordinate multiple metal ions both along the backbone and within its central cavity.
Topics: Crystallography, X-Ray; Pyrenes; Spectrometry, Fluorescence
PubMed: 35358383
DOI: 10.1021/jacs.2c01605 -
The Science of the Total Environment May 2022Soil microbial diversity is an essential driver of multiple ecosystem functions and services. However, the role and mechanisms of microbial diversity in the dissipation...
Soil microbial diversity is an essential driver of multiple ecosystem functions and services. However, the role and mechanisms of microbial diversity in the dissipation of persistent organic pollutants in soil are largely unexplored. Here, a gradient of soil microbial diversity was constructed artificially by a dilution-to-extinction approach to assess the role of soil microbial diversity in the dissipation of pyrene, a high molecular weight polycyclic aromatic hydrocarbon (PAH), in a 42-day microcosm experiment. The results showed that pyrene dissipation (98.1%) and the abundances of pyrene degradation genes (the pyrene dioxygenase gene nidA and the gram-positive PAH-ring hydroxylating dioxygenase gene PAH-RHDα GP) were highest in soils with high microbial diversity. Random-forest machine learning was combined with linear regression analysis to identify a range of keystone taxa (order level) associated with pyrene dissipation, including Sphingobacteriales, Vampirovibrionales, Blastocatellales, Myxococcales, Micrococcales and Rhodobacterales. The diversity of these keystone taxa was significantly and positively correlated with the abundance of pyrene degradation genes and the removal rate of pyrene. According to (partial) Mantel tests, keystone taxa diversity was the dominant factor determining pyrene dissipation compared with total microbial diversity. Moreover, co-occurrence network analysis revealed that diverse keystone taxa may drive pyrene dissipation via more positive interactions between keystone species and with other species in soil. Taken together, these findings provide new insights on the regulation of keystone taxa diversity to promote the dissipation of PAH in soil.
Topics: Biodegradation, Environmental; Ecosystem; Polycyclic Aromatic Hydrocarbons; Pyrenes; Soil; Soil Microbiology; Soil Pollutants
PubMed: 35038522
DOI: 10.1016/j.scitotenv.2022.153082 -
Journal of Hazardous Materials Oct 2023The study of anaerobic high molecular weight polycyclic aromatic hydrocarbons (HMW-PAHs) biodegradation under sulfate-reducing conditions by microorganisms, including...
The study of anaerobic high molecular weight polycyclic aromatic hydrocarbons (HMW-PAHs) biodegradation under sulfate-reducing conditions by microorganisms, including microbial species responsible for biodegradation and relative metabolic processes, remains in its infancy. Here, we found that a new sulfate-reducer, designated as Desulforamulus aquiferis strain DSA, could biodegrade pyrene and benzo[a]pyrene (two kinds of HMW-PAHs) coupled with the reduction of sulfate to sulfide. Interestingly, strain DSA could simultaneously biodegrade pyrene and benzo[a]pyrene when they co-existed in culture. Additionally, the metabolic processes for anaerobic pyrene and benzo[a]pyrene biodegradation by strain DSA were newly proposed in this study based on the detection of intermediates, quantum chemical calculations and analyses of the genome and RTqPCR. The initial activation step for anaerobic pyrene and benzo[a]pyrene biodegradation by strain DSA was identified as the formation of pyrene-2-carboxylic acid and benzo[a]pyrene-11-carboxylic acid by carboxylation Thereafter, CoA ligase, ring reduction through hydrogenation, and ring cracking occurred, and short-chain fatty acids and carbon dioxide were identified as the final products. Additionally, DSA could also utilize benzene, naphthalene, anthracene, phenanthrene, and benz[a]anthracene as carbon sources. Our study can provide new guidance for the anaerobic HMW-PAHs biodegradation under sulfate-reducing conditions.
Topics: Benzo(a)pyrene; Anaerobiosis; Sulfates; Pyrenes; Polycyclic Aromatic Hydrocarbons; Anthracenes; Biodegradation, Environmental
PubMed: 37482040
DOI: 10.1016/j.jhazmat.2023.132053 -
Biosensors Jul 2022Aggregation-induced emission (AIE) is a unique research topic and property that can lead to a wide range of applications, including cellular imaging, theranostics,... (Review)
Review
Aggregation-induced emission (AIE) is a unique research topic and property that can lead to a wide range of applications, including cellular imaging, theranostics, analyte quantitation and the specific detection of biologically important species. Towards the development of the AIE-active materials, many aromatic moieties composed of tetraphenylethylene, anthracene, pyrene, etc., have been developed. Among these aromatic moieties, pyrene is an aromatic hydrocarbon with a polycyclic flat structure containing four fused benzene rings to provide an unusual electron delocalization feature that is important in the AIE property. Numerous pyrene-based AIE-active materials have been reported with the AIE property towards sensing, imaging and theranostics applications. Most importantly, these AIE-active pyrene moieties exist as small molecules, Schiff bases, polymers, supramolecules, metal-organic frameworks, etc. This comprehensive review outlines utilizations of AIE-active pyrene-based materials on the imaging and theranostics studies. Moreover, the design and synthesis of these pyrene-based molecules are delivered with discussions on their future scopes.
Topics: Polymers; Precision Medicine; Pyrenes
PubMed: 35884351
DOI: 10.3390/bios12070550 -
Bioorganic & Medicinal Chemistry May 2023In this work, we report the design, synthesis, and application of a bis-pyrene phospholipid probe for detection of phospholipase A action through changes in pyrene...
In this work, we report the design, synthesis, and application of a bis-pyrene phospholipid probe for detection of phospholipase A action through changes in pyrene monomer and excimer fluorescence intensities. Continuous fluorometric assays enabled detection of the activities of multiple PLA enzymes as well as the decrease in catalysis by PLA from honey bee venom caused by the inhibitor p-bromo phenacylbromide. Thin-layer chromatography and mass spectrometry analysis were also used to validate probe hydrolysis by PLA. Mass spectrometry data also supported cleavage of the probe by phospholipase C and D enzymes, although changes in fluorescence were not observed in these cases. Nevertheless, the bis-pyrene phospholipid probe developed in this work is effective for detection of PLA enzyme activity through an assay that enables screening for inhibitor development.
Topics: Hydrolysis; Phospholipases; Phospholipases A2; Phospholipids; Pyrenes
PubMed: 37150117
DOI: 10.1016/j.bmc.2023.117301 -
International Journal of Molecular... Jul 2021Microbial biodegradation is one of the acceptable technologies to remediate and control the pollution by polycyclic aromatic hydrocarbon (PAH). Several bacteria, fungi,... (Review)
Review
Microbial biodegradation is one of the acceptable technologies to remediate and control the pollution by polycyclic aromatic hydrocarbon (PAH). Several bacteria, fungi, and cyanobacteria strains have been isolated and used for bioremediation purpose. This review paper is intended to provide key information on the various steps and actors involved in the bacterial and fungal aerobic and anaerobic degradation of pyrene, a high molecular weight PAH, including catabolic genes and enzymes, in order to expand our understanding on pyrene degradation. The aerobic degradation pathway by PRY-1 and sp. KMS and the anaerobic one, by the facultative bacteria anaerobe sp. JP1 and sp. LZ6 are reviewed and presented, to describe the complete and integrated degradation mechanism pathway of pyrene. The different microbial strains with the ability to degrade pyrene are listed, and the degradation of pyrene by consortium is also discussed. The future studies on the anaerobic degradation of pyrene would be a great initiative to understand and address the degradation mechanism pathway, since, although some strains are identified to degrade pyrene in reduced or total absence of oxygen, the degradation pathway of more than 90% remains unclear and incomplete. Additionally, the present review recommends the use of the combination of various strains of anaerobic fungi and a fungi consortium and anaerobic bacteria to achieve maximum efficiency of the pyrene biodegradation mechanism.
Topics: Klebsiella; Microbial Consortia; Mycobacterium; Oxygen; Pseudomonas; Pyrenes
PubMed: 34360967
DOI: 10.3390/ijms22158202 -
Journal of Hazardous Materials Feb 2022Bioaugmentation is an effective approach to remediate soils contaminated by polycyclic aromatic hydrocarbons (PAHs), but suffers from unsatisfactory performance in...
Bioaugmentation is an effective approach to remediate soils contaminated by polycyclic aromatic hydrocarbons (PAHs), but suffers from unsatisfactory performance in engineering practices, which is hypothetically explained by the complicated interactions between indigenous microbes and introduced degraders. This study isolated a cultivable pyrene degrader (Sphingomonas sp. YT1005) and an active pyrene degrading consortium (Gp16, Streptomyces, Pseudonocardia, Panacagrimonas, Methylotenera and Nitrospira) by magnetic-nanoparticle mediated isolation (MMI) from soils. Pyrene biodegradation was postponed in bioaugmentation with Sphingomonas sp. YT1005, whilst increased by 30.17% by the active pyrene degrading consortium. Pyrene dioxygenase encoding genes (nidA, nidA3 and PAH-RHDα-GP) were enriched in MMI isolates and positively correlated with pyrene degradation efficiency. Pyrene degradation by Sphingomonas sp. YT1005 only followed the phthalate pathway, whereas both phthalate and salicylate pathways were observed in the active pyrene degrading consortium. The results indicated that the uncultivable pyrene degraders were suitable for bioaugmentation, rather than cultivable Sphingomonas sp. YT1005. The negative correlations between Sphingomonas sp. YT1005 and the active-yet-uncultivable pyrene degraders were the underlying mechanisms of bioaugmentation postpone in engineering practices.
Topics: Biodegradation, Environmental; Polycyclic Aromatic Hydrocarbons; Pyrenes; Soil Microbiology; Soil Pollutants
PubMed: 34555764
DOI: 10.1016/j.jhazmat.2021.127189 -
Journal of Hazardous Materials Aug 2021The present study was conducted to compare the efficiency of different microbial mixed-cultures consists of fifteen oil-degrading microorganisms with different...
The present study was conducted to compare the efficiency of different microbial mixed-cultures consists of fifteen oil-degrading microorganisms with different combinations. The investigation was targeted toward the removal of 500 mg/l pyrene and 1% w/v tetracosane, as single compounds or mixture. Sequential Fungal-Bacterial Mixed-Culture (SMC) in which bacteria added one week after fungi, recorded 60.76% and 73.48% degradation for pyrene and tetracosane; about 10% more than Traditional Fungal-Bacterial Mixed-Culture (TMC). Co-degradation of pollutants resulted in 24.65% more pyrene degradation and 6.41% less tetracosane degradation. The non-specified external enzymes of fungi are responsible for initial attacks on hydrocarbons. Delayed addition of bacteria and co-contamination would result in higher growth of fungi which increases pyrene degradation. The addition of Rhamnolipid potently increased the extent of pyrene and tetracosane degradation by approximately 16% and 23% and showed twice better performance than Tween-80 in 20 times less concentration. The results indicated the importance of having sufficient knowledge on the characteristics of the contaminated site and its contaminants as well as oil-degrading species. Gaining this knowledge and using it properly, such as the later addition of bacteria (new method of mixed-cultures inoculation) to the contaminated culture, can serve as a promising approach.
Topics: Alkanes; Bacteria; Biodegradation, Environmental; Fungi; Polycyclic Aromatic Hydrocarbons; Pyrenes; Soil Microbiology; Soil Pollutants
PubMed: 34492965
DOI: 10.1016/j.jhazmat.2021.126202