The fungus Cunninghamella elegans ATCC 36112 metabolized approximately 80% of the (3-14)C-labeled fluoranthene (FA) added within 72 hr of incubation. C. elegans metabolized FA to trans-2,3-dihydroxy-2,3-dihydrofluoranthene (trans-2,3-dihydrodiol), 8- and 9-hydroxyfluoranthene trans-2,3-dihydrodiol, 3-fluoranthene-beta-glucopyranoside, and 3-(8-hydroxyfluoranthene)-beta-glucopyranoside. These metabolites were separated by thin-layer and reversed-phase high-performance liquid chromatography and identified by 1H nuclear magnetic resonance, UV, and mass spectral techniques. The major pathway involved hydroxylation to form a glucoside conjugate of 3-hydroxyfluoranthene and a glucoside conjugate of 3,8-dihydroxyfluoranthene which together accounted for 52% of the total ethyl acetate-soluble metabolites. C. elegans initially metabolized FA in the 2,3 position to form fluoranthene trans-2,3-dihydrodiol, which has previously been shown to be a biologically active compound in mammalian and bacterial genotoxicity tests. However, C. elegans formed predominantly glucoside conjugates of the phenolic derivatives of FA, which suggests that this fungus has the potential to detoxify FA.
The 2,3-dihydrodiol has been detected as a metabolite of fluoranthene following incubation of this compound with a rat-liver preparation. The 2,3-dihydriol was found to be mutagenic to bacteria in the presence of a metabolic activation system.
The metabolite of fluoranthene ... obtained upon incubation with liver homogenate from Aroclor pretreated rats ... 2,3-dihydro-2,3-dihydroxyfluoranthene.
Adverse health effects such as cancer and toxicity may be attributed to consumption of chemically contaminated food rich in fat. This leads to a larger intake and retention of lipophilic toxic chemicals in the body with an increase in risks to human health. The objective of this study was to characterize the effect of dietary fat on disposition and metabolism of fluoranthene (FLA), a polycyclic aromatic hydrocarbon compound. FLA was administered to F-344 rats in monounsaturated (peanut oil), polyunsaturated (corn oil) and saturated (coconut oil) fats at doses of 50 and 100 ug/kg via oral gavage. Blood, small intestine, liver, lung, testis, adipose tissue, urine and feces were collected at various time points' post-FLA exposure. Samples were analyzed by reverse-phase high-performance liquid chromatography for FLA parent compound and metabolites. DNA was isolated from the tissues and subjected to (32)P-post labeling to measure FLA-DNA adducts. The concentrations of unchanged FLA (FLA parent compound) and its metabolites showed an increase for the saturated fat treatment group compared with mono- and polyunsaturated fat groups. The FLA-DNA adduct concentrations were high in tissues of rats that received FLA through saturated fat. The toxicokinetic parameters, concentrations of FLA metabolites and FLA-DNA adduct showed a dose-dependent increase, and this increase was statistically significant (P<.05) for saturated fat. These findings clearly demonstrate that the high residence time of FLA parent compound in saturated fat allows extensive metabolism, contributing reactive metabolites of FLA that bind with DNA and causing marked damage in a long-term exposure scenario.
PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (L10)
IDENTIFICATION AND USE: Fluoranthene is a solid. Currently, there is no known production of or use of this compound. Polycyclic aromatic hydrocarbons are a group of chemicals that are formed during the incomplete burning of coal, oil, gas, wood, garbage, or other organic substances, such as tobacco and charbroiled meat. HUMAN EXPOSURE AND TOXICITY: Fluoranthene was mutagenic to cultured human Iymphoblastoid cells in the presence of an exogenous metabolic system. It is confirmed human carcinogen. ANIMAL STUDIES: A 24 week lung adenoma bioassay using newborn mice was employed to determine the tumorigenicity of fluoranthene. A 6.5-fold elevation of lung tumor incidence (58%) and a 12-fold increase in numbers (1.08 tumors/mouse) was observed in animals treated with the highest dose (3.5 mg/mouse), but no increase in tumor incidence was induced by 700 micrograms/mouse. In other experiment, fluoranthene induced lung and liver tumors 6-9 months after intraperitoneal injection of 0.7, 1.75 and 3.5 mg into preweanling mice. Although fluoranthene is mutagenic in bacterial and mammalian in vitro cell systems following metabolic activation, information on in vivo mutagenicity is lacking and studies on tumor initiating activity in mice are equivocal. Fluoranthene can produce behavioral toxicity in rats. Fluoranthene could also compromise B lymphopoiesis. A developmental study was performed in which fluoranthene was administered once via intraperitoneal injection to pregnant C57/B6 mice on gestational day 6, 7, 8 or 9. An increased rate of embryo resorption was observed. ECOTOXICITY STUDIES: The acute and chronic toxicity of fluoranthene was determined for a diverse group of freshwater and saltwater species under both standard laboratory fluorescent light and ultraviolet (UV) light test conditions. Acute tests with 21 species demonstrated that fluoranthene was not lethal within its water solubility limit to most species tested under fluorescent light, but was lethal well below this limit to nearly all of the species tested under UV light. Overall, UV light increased acute fluoranthene toxicity approximately one to three orders of magnitude.
The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (L10, L23, A27, A32)
CLASSIFICATION: D; not classifiable as to human carcinogenicity. BASIS FOR CLASSIFICATION: Based on no human data and inadequate data from animal bioassays. HUMAN CARCINOGENICITY DATA: None. ANIMAL CARCINOGENICITY DATA: Inadequate.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
致癌性证据
没有关于人类的数据。动物致癌性证据不足。总体评估：第3组：该物质对人类致癌性无法分类。
No data are available in humans. Inadequate evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
致癌物分类
国际癌症研究机构致癌物：荧蒽
IARC Carcinogenic Agent:Fluoranthene
来源:International Agency for Research on Cancer (IARC)
The dose-dependence of hemoglobin binding as well as distribution of fluoranthene and fluoranthene-DNA adducts in various tissues was characterized in male rats 24 hr after a single i.p. injection of (3)H-fluoranthene. Formation and distribution of DNA adducts after chronic administration of fluoranthene in the diet was also studied. Fluoranthene-derived radioactivity was widely distributed throughout the animal after a single dose, and excreta contained the greatest amounts of radioactivity at all dose levels. Fluoranthene binding to globin was proportional to dose over the range of 2 nmol/kg to 177 umol/kg, and the adducted protein was cleared at the same rate as unmodified hemoglobin, indicating that the adducts are stable in vivo. In contrast, fluoranthene-DNA adducts were not present at detectable levels in liver or kidney 24 hr after one dose; low levels of adducts were found only in the lung at the highest dose level. Chronic administration of fluoranthene in the diet, however, resulted in DNA adduct formation in most tissues examined, including liver, kidney, lung, small intestine, heart, spleen and lymphocytes; adducts were not detectable in testes DNA. The major fluoranthene-DNA adduct found in rat tissues was identified by its chromatographic similarity to the major fluoranthene adduct formed in vitro using microsomally-activated fluoranthene and calf thymus DNA, previously identified as a reaction product of anti-2,3-dihydroxy-1,10b-epoxy-1,2,3-trihydro-fluoranthene with N2-deoxyguanosine. The unusual stability of this diol epoxide at physiological pH may allow transport of this ultimate DNA-binding metabolite to virtually all tissues. These results demonstrate the applicability of the HPLC-(32)P-postlabelling procedure to detect and quantify fluoranthene-DNA adducts formed in vivo, and suggest that analysis of these adducts in accessible tissues such as lymphocytes may be a means of assessing chronic, high level exposure to fluoranthene. Our results also indicate that hemoglobin adducts of fluoranthene could be useful dosimeters for detecting short-term or chronic exposure to this compound if a suitable method for their detection were developed.
/MILK/ Polycyclic aromatic hydrocarbons (PAHs) were analyzed in maternal blood and fetuses from Fischer 344 rats exposed to diesel exhaust (DE) during pregnancy, and in breast milk from rats exposed to DE during pregnancy and lactation using high performance liquid chromatography with fluorescence detection. Concentrations of phenanthrene (Phe), anthracene (Ant) and benz[a]anthracene (BaA) were significantly higher in maternal blood of the DE group than those of the control group. Concentration of Phe in fetuses of the DE group was significantly higher than those of the control group. Concentrations of fluorene, Ant, fluoranthene (Flu), pyrene (Pyr), BaA and chrysene (Chr) tended to be higher in fetuses of the DE group. The levels of Ant, Flu, Pyr and Chr in breast milk from the DE group were significantly higher than those of the control group. These results indicate that PAHs taken into mother rat by the inhalation of DE are transferred into fetuses via placenta and into breast milk. ...
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
芴苯已在人类尿液和粪便中被发现。
Fluoranthene has been found in human urine and feces.
Blood levels of fluoranthene, pyrene, and benz[a]anthracene after oral administration were examined in rats. Fluoranthene, pyrene, or benz[a]anthracene in Tween 80/isotonic saline, was administered orally to rats at a dose of 20 mg/kg. Blood levels after administration indicated that peak concentrations of the three compounds were reached at 1-2 hours after administration. The peak concentration of fluoranthene (approximately 30 mg/cu cm) was twice as high as that of pyrene, and 5 times higher than benz[a]anthracene.
Les ethers du titre subissent une scission de la liaison H 2 CO lorsqu'ils sont traites par les radicaux anioniques de l'anthracene ou du fluoranthrene。Dans des conditions 可比 les naphtylmethyl phenyl ethers reagisent plus de 10 4 fois plus vite que lesnaphtylbenzyl ethers。解释
ORGANIC ELECTROLUMINESCENCE DEVICE AND ANTHRACENE DERIVATIVE
申请人：IKEDA Hidetsugu
公开号：US20110034744A1
公开（公告）日：2011-02-10
An anthracene derivative having a specific asymmetric structure is provided. The asymmetric anthracenes are useful in an organic electroluminescence device and exhibit efficient light emission and a long performance lifetime.
Birch‐Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer
作者：Anamitra Chatterjee、Burkhard König
DOI：10.1002/anie.201905485
日期：2019.10
energy-transfer and electron-transfer processes generates an arene radical anion, which is subsequently trapped by hydrogen-atom transfer and finally protonated to form the dearomatized product. The photoreduction converts planar aromatic feedstock compounds into molecular skeletons that are of use in organic synthesis.
[EN] NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME<br/>[FR] NOUVEAUX COMPOSÉS ÉLECTROLUMINESCENTS ORGANIQUES ET DISPOSITIF ÉLECTROLUMINESCENT ORGANIQUE LES UTILISANT
申请人：ROHM & HAAS ELECT MAT
公开号：WO2013032278A1
公开（公告）日：2013-03-07
The present invention relates to a novel compound and an organic electroluminescent device containing the same. Since the compounds according to the present invention have high efficiency in transporting electrons, crystallization could be prevented when manufacturing the device, and since they are adaptable in the formation of the layers, the current characteristic of the device is improved, and finally they can manufacture an organic electroluminescent device having lowered driving voltage, advanced power efficiency, and improved light emitting efficiency and lifetime characteristic compared with devices comprising the conventional materials.
Arynes are found to be facilely inserted into bis(pinacolato)diboron by using a platinum–isocyanide catalyst, affording diverse 1,2-diborylarenes, which can be converted into o-terphenyls via Suzuki–Miyaura coupling reaction.
Preparation of Substituted Phenanthridines from the Coupling of Aryldiazonium Salts with Nitriles: A Metal Free Approach
作者：Mani Ramanathan、Shiuh-Tzung Liu
DOI：10.1021/acs.joc.5b00579
日期：2015.5.15
A transition metal free approach for the synthesis of substituted phenanthridines from the coupling reaction of aryldiazonium tetrafluoroborates with nitriles has been developed. This operationally simple protocol proceeds through a substitution of aryldiazonium with nitriles followed by an intramolecular arylation to provide the corresponding phenanthridines in moderate to excellent yields.
