Non-intuitive clustering of 9,10-phenanthrenequinone on Au(111)

Brown, Ryan D.; Quardokus, Rebecca C.; Wasio, Natalie A.; Petersen, Jacob P.; Silski, Angela M.; Corcelli, Steven A.; Kandel, S. Alex

doi:10.3762/bjnano.8.181

Cited by 8 publications

(10 citation statements)

References 39 publications

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“…We have shown that these nonequilibrium conditions can produce metastable 2D structures. [33][34][35]43 According to Ostwald's rule, 44 the least stable species will precipitate out first, potentially becoming kinetically locked on the surface. Although there are examples of solvent-controlled 2D polymorphism at the liquid−solid interface, 45−47 neither the phthalimide tetramer networks nor the isatin pentamers were solvent-dependent species (Figure S4).…”

Section: ■ Methodsmentioning

confidence: 99%

Scanning Tunneling Microscopy Investigation of Two-Dimensional Polymorphism of Structural Isomers

et al. 2018

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Monolayers of two pairs of structural isomers were deposited on Au(111) and observed via scanning tunneling microscopy in ultrahigh vacuum. We observe exclusively cyclic pentamers of isatin (1H-indole-2,3-dione), whereas its structural isomer, phthalimide (isoindole-1,3-dione), self-assembles primarily into close-packed arrays, with alternate structures that include kinetically locked disordered clusters and tetramer networks. Removal of the phthalimide NH group and its replacement with a CH2 group produces 1,3-indandione, which, despite the loss of the hydrogen-bond donor site, self-assembles into similar structures: close-packed areas and tetramer networks. The equivalent analog for isatin, 1,2-indandione, does not form pentamers and instead forms only close-packed areas and disordered regions. By iteratively altering the chemical structure, we demonstrate the influence that the chemical structure has on the resulting two-dimensional self-assembly.

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Section: ■ Methodsmentioning

confidence: 99%

Scanning Tunneling Microscopy Investigation of Two-Dimensional Polymorphism of Structural Isomers

et al. 2018

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“…As one of the most abundant quinones found in DEPs [ 43 ], when inhaled, 9,10-PQ can be generated from phenanthrene by P-450s as below pathway [ 37 ]. Phenanthrene is one of major PAHs present in the air pollution [ 37 – 52 ].…”

Section: 910-phenanthrenequinone Is One Of the Major Components Omentioning

confidence: 99%

“…As a redox-active quinone in diesel exhausts, 9,10-PQ has been shown to generate ROS ( Figure 2 ) via its redox cycling resulting in its toxicity [ 37 – 52 , 57 , 62 , 63 , 67 , 71 – 88 ] in vitro and in vivo. 9,10-PQ can accept an electron to produce the semiquinone form of 9,10-PQ [ 70 ].…”

Section: Redox Cycling Of 910-pq In the Generation Of Reactive Oxmentioning

confidence: 99%

“…Understanding the toxic role of quinones is of great interest as this allows for the development of novel therapeutics designed to specifically target downstream mediators. Exposure to 9,10-PQ containing particulate matter (PM) has been associated with the development of many disease processes including lung cancer, asthma, and allergic inflammation [ 37 – 52 ].…”

Section: Introductionmentioning

confidence: 99%

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Cytotoxicity of Air Pollutant 9,10-Phenanthrenequinone: Role of Reactive Oxygen Species and Redox Signaling

Yang

Ahmed

et al. 2018

BioMed Research International

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Atmospheric pollution has been a principal topic recently in the scientific and political community due to its role and impact on human and ecological health. 9,10-phenanthrenequinone (9,10-PQ) is a quinone molecule found in air pollution abundantly in the diesel exhaust particles (DEP). This compound has studied extensively and has been shown to develop cytotoxic effects both in vitro and in vivo. 9, 10-PQ has been proposed to play a critical role in the development of cytotoxicity via generation of reactive oxygen species (ROS) through redox cycling. This compound also reduces expression of glutathione (GSH), which is critical in Phase II detoxification reactions. Understanding the underlying cellular mechanisms involved in cytotoxicity can allow for the development of therapeutics designed to target specific molecules significantly involved in the 9,10-PQ-induced ROS toxicity. This review highlights the developments in the understanding of the cytotoxic effects of 9, 10-PQ with special emphasis on the possible mechanisms involved.

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“…The results show the endocrine system interference, cytotoxicity, genetic toxicity, and carcinogenicity of oxy-PAHs. One type of oxy-PAH, 9,10-phenanthraquinone (9,10-PQ), induces the production of reactive oxygen species (ROS) (9,17,31,46,67) and causes apoptotic cell death at submicromolar concentrations (49). The average concentration of 9,10-PQ in airborne particulates is 0.287 Ϯ 0.128 ppm (88).…”

Section: Introductionmentioning

confidence: 99%

Transcriptome changes ofTakifugu obscurusliver after acute exposure to the oxygenated-PAH 9,10-phenanthrenequione

Jiang

Yang

Fang

2020

Physiological Genomics

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Contamination with polycyclic aromatic hydrocarbons (PAHs) causes noticeable ecological problems in aquatic ecosystems. 9,10-phenanthrenequione (9,10-PQ) is an oxidized PAH and is highly toxic to aquatic animals. However, the effects of 9,10-PQ on the molecular metabolism of fish remain largely unknown. In this study, Takifugu obscurus juveniles were acutely exposed to 44.30 µg/L 9,10-PQ for three days. The transcriptome profile changes in their livers were compared between the 9,10-PQ treatment group and the control using T. rubripes as the reference genome. The results identified 22,414 genes in our transcriptome. Among them, 767 genes were differentially expressed (DEGs) after exposure to 9,10-PQ, which enriched 16 KEGG pathways. Among them, the glycolysis, phagosome, and FOXO signaling pathways were significantly activated in 9,10-PQ treatment compared with the control. These data indicate that 9,10-PQ increased the glycolysis capacity to produce more energy for resistance and harmed immune function. Moreover, several genes related to tumorigenesis were significantly up-regulated in response to 9,10-PQ, displaying the carcinogenic toxicity of 9,10-PQ to T. obscurus. Genes in steroid biosynthesis pathways were down-regulated in the 9,10-PQ treatment group, suggesting interference with the endocrine system. Overall, these findings provide information to help evaluate the environmental risks that oxygenated-PAHs present to T. obscurus.

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Non-intuitive clustering of 9,10-phenanthrenequinone on Au(111)

Cited by 8 publications

References 39 publications

Scanning Tunneling Microscopy Investigation of Two-Dimensional Polymorphism of Structural Isomers

Scanning Tunneling Microscopy Investigation of Two-Dimensional Polymorphism of Structural Isomers

Cytotoxicity of Air Pollutant 9,10-Phenanthrenequinone: Role of Reactive Oxygen Species and Redox Signaling

Transcriptome changes ofTakifugu obscurusliver after acute exposure to the oxygenated-PAH 9,10-phenanthrenequione

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