Dibenzo[a,i]pyrene (10 umol) was metabolized to partially characterized phenols and dihydrodiols by mixed-function oxidases in liver homogenates and microsomes from 3-methylcholanthrene pretreated rats.
1,2 & 3,4-dihydrodiols have been reported to be metabolites of dibenzo[a,i]pyrene following incubation of this compound with rat-liver preparations. The 3,4-dihydrodiol has been reported to be mutagenic to bacteria in the presence of an exogenous metabolic system; it is a tumor initiator on mouse skin and tumorigenic in newborn mice.
IDENTIFICATION AND USE: Dibenzo(a,i)pyrene (DB(a,i)P) forms greenish-yellow needles, prisms or lamellae. It is used as an experimental carcinogen. HUMAN EXPOSURE AND TOXICITY: DB(a,i)P is reasonably anticipated to be a human carcinogen. DB(a,i)P was mutagenic in the Ames test, in the presence of hepatic post-mitochondrial preparations isolated from man. ANIMAL STUDIES Groups of 20 female mice received 10 dermal applications of DB(a,i)P (total doses, 100 ug and 500 ug). Ten days after initiation had been completed, all animals received applications of 2.5 ug 12-O-tetradecanoylphorbol-13-acetate (TPA) for 20 weeks. Mice treated with 100 ug DB(a,i)P had a 40% skin tumor incidence (average of 0.5 skin tumors/mouse), whereas the group treated with 500 ug DB(a,i)P had an 85% skin tumor incidence (average of 5.8 skin tumors/mouse). A group of 20 female rats received intramamillary injection of 4 umol (1.2 mg)/gland DB(a,i)P and another was untreated. At the end of the study, 18/19 rats in the DB(a,i)P-treated group had developed fibrosarcomas (2.4 tumors/tumor-bearing rat), 11/19 rats had mammary adenocarcinomas (1.4 tumors/tumor-bearing rat) and 1/19 had mammary adenofibromas (two tumors). In contrast, 2/20 rats in the untreated group had developed mammary epithelial tumors (one adenofibroma and one adenocarcinoma) but no fibrosarcomas. Dermal exposure to DB(a,i)P caused benign or malignant skin tumors (papilloma or epithelioma) in mice, and subcutaneous injection caused cancer at the injection site (sarcoma) in mice and hamsters. DB(a,i)P was mutagenic in the in the Ames test, in the presence of hepatic post-mitochondrial preparations isolated from the mouse, rat, hamster, and pig. It did not induce DNA damage in mammalian cells in vitro. ECOTOXICITY STUDIES: DB(a,i)P induced 7-ethoxyresorufin-o-deethylase activity in the rainbow trout liver cell line.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
致癌性证据
2B组:该物质对人类可能是致癌的。
Group 2B: The agent is possibly carcinogenic to humans.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
致癌性证据
二苯并(a,i)芘:合理预期为人类致癌物。/多环芳烃/
Dibenzo(a,i)pyrene: reasonably anticipated to be a human carcinogen. /Polycyclic Aromatic Hydrocarbons/
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:二苯并[a,i]芘
IARC Carcinogenic Agent:Dibenzo[a,i]pyrene
来源:International Agency for Research on Cancer (IARC)
毒理性
致癌物分类
国际癌症研究机构(IARC)致癌物分类:2B组:可能对人类致癌
IARC Carcinogenic Classes:Group 2B: Possibly carcinogenic to humans
来源:International Agency for Research on Cancer (IARC)
... C57BL/6 Jax mice /were injected/ sc with 500 ug (14)C-labelled DB(a,i)P in peanut oil. Distribution of radioactivity between injection sites and organs was determined ... 85% of carcinogen is removed from injection site and ... removal was nearly complete in 10 wk.
Emission Factors and Importance of PCDD/Fs, PCBs, PCNs, PAHs and PM<sub>10</sub> from the Domestic Burning of Coal and Wood in the U.K.
作者:Robert G. M. Lee、Peter Coleman、Joanne L. Jones、Kevin C. Jones、Rainer Lohmann
DOI:10.1021/es048745i
日期:2005.3.1
fuels. However, their combined emissions from the domestic burning of coal and wood would contribute only a few percent to annual U.K.emission estimates. Emissions of PAHs and PM10 were major contributors to U.K. national emission inventories. Major emissions were found from the domestic burning for Cl1,2,3DFs, while the contribution of PCDD/F-sigmaTEQ to total U.K.emissions was minor.
本文介绍了当煤和木材经过受控燃烧实验时针对一系列持久性有机污染物(POPs)得出的排放因子(EFs),旨在模拟空间供暖的家庭燃烧。排放了各种各样的持久性有机污染物,煤炭的排放量高于木材的排放量。对于颗粒物,PM10(大约10 g / kg燃料)和多环芳烃(对于sigmaPAHs大约100 mg / kg燃料)获得了最高的EF。对于氯化物,多氯联苯(PCB)的EF最高,而多氯萘(PCN),二苯并-对-二恶英(PCDD)和二苯并呋喃(PCDF)的丰度较低。对于sigmaPCB,EF大约为1000 ng / kg燃料,对于sigmaPCNs大约为100s ng / kg燃料,对于sigmaPCDD / Fs大约为100 ng / kg燃料。该研究证实,一氯化至三氯化二苯并呋喃Cl1,2,3DFs是低温燃烧过程(如煤炭和木材的国内燃烧)的有力指标。结论是,在固体燃料燃烧期间通常形成许多PCB和PC
On-Surface Synthesis of Dibenzohexacenohexacene and Dibenzopentaphenoheptaphene
作者:Xiushang Xu、Amogh Kinikar、Marco Di Giovannantonio、Pascal Ruffieux、Klaus Müllen、Roman Fasel、Akimitsu Narita
DOI:10.1246/bcsj.20200382
日期:2021.3.15
Abstract
We report the on-surface synthesis and gas-phase theoretical studies of two novel nanographenes, namely, dibenzohexacenohexacene and dibenzopentaphenoheptaphene, using 8,8′-dibromo-5,5′-bibenzo[rst]pentaphene as a precursor. These nanographenes display a combination of armchair and zigzag edges, as shown by noncontact atomic force microscopy (nc-AFM), and their electronic properties are elucidated by density functional theory (DFT) calculations which reveal relatively low HOMO-LUMO energy gaps of about 1.75 eV.
A new general synthesis of polycyclic aromatic compounds based on enamine chemistry
作者:Ronald G. Harvey、John Pataki、Cecilia Cortez、Pasquale Di Raddo、Cheng Xi Yang
DOI:10.1021/jo00003a050
日期:1991.2
Alkylation of enamines and enamine salts by benzylic and (beta-haloethyl)aryl halides, respectively, followed by acidic cyclodehydration and dehydrogenation provides an efficient synthetic approach to a wide range of polycyclic aromatic compounds of diverse structural types. Specific polycyclic hydrocarbons synthesized by this route include benzo[a]- and benzo[c]fluorene, 7H-dibenzo[c,g]-, 13H-dibenzo[a,i]-, and 13H-dibenzo[a,g]fluorene, 15H-tribenzo[a,c,i]fluorene, dibenzo[b,def]chrysene, benzo[rst]pentaphene, indeno[1,2-b]fluorene, fluoreno[3,4-c]fluorene, octahydrodibenz[a,j]anthracene, dibenz[a,j]anthracene, octahydrodibenz[a,h]anthracene, dibenz[a,h]anthracene, dibenz[a,h]anthracene, picene, benzo[c]picene, 1H-benz[bc]aceanthrylene, and 4H-cyclopenta[def]chrysene. This method with appropriate modifications appears to be potentially broader in scope than established traditional methods of polycyclic hydrocarbon synthesis.
Benzannelated annulenes. 8. Toward the understanding of benzannelated annulenes: synthesis and properties of [a,h]- and [a,i]-ring dibenzannelated dihydropyrenes
作者:Reginald H. Mitchell、Richard Vaughan Williams、Thomas W. Dingle
DOI:10.1021/ja00373a038
日期:1982.5
Synthesis of Dibenzopyrenes and Pyrenes via Photolytic Sulfur Extrusion and Intramolecular Cross-Coupling Reactions of Dithia[3.3](1,3)naphthalenophanes and Dithia[3.3]metacyclophanes
作者:Muhammad Ashram、David O. Miller、John N. Bridson、Paris E. Georghiou
DOI:10.1021/jo970181w
日期:1997.9.1
The syntheses of several substituted dithia[3.3]metacyclophanes and dithia[3.3](1,3)naphthalenophanes are reported and their photolyses in triethyl or trimethyl phosphite are described. Under these conditions, the corresponding tetrahydrodibenzopyrenes and tetrahydropyrenes are produced in a one-pot procedure when the precursor dithianaphthalenophanes and dithiacyclophanes possess at least one intraannular methoxyl group. A mechanism with supporting evidence is proposed to account for these results. Structural determinations of the four isomeric 11,22-dimethoxy-2,13-dithia[3.3](1,3)naphthalenophanes by NMR and X-ray single-crystal diffraction studies are also described. The syntheses of the novel anti-transoid- and anti-cisoid-[2.2](1,3)naphthalenophanes are also described.