Disease relevance of dibenzofuran

• Several members of the class, including certain polychlorinated biphenyls (PCBs) and polychlorinated dibenzofurans and dibenzodioxins, produce a characteristic toxicity syndrome, manifestations of which are increased mortality, oedema, hyperkeratosis, thymic involution and hepatotoxicity [1].
• In this work, we describe the evolved biphenyl dioxygenase (BPDO) RR41 that exhibits a higher turnover rate of metabolism toward dibenzofuran and chlorodibenzofurans than the parental Burkholderia xenovorans LB400 BPDO [2].
• C. elegans also oxidized dibenzofuran to 2- and 3-hydroxydibenzofuran under conditions that would not lead to the dehydration of the trans-dihydrodiol [3].
• Cunninghamella elegans and a mutant strain (B8/36) of Beijerinckia both oxidized dibenzofuran to 2,3-dihydroxy-2,3-dihydrodibenzofuran [3].
• Dibenzofuran 4,4a-dioxygenase from Sphingomonas sp. strain RW1: angular dioxygenation by a three-component enzyme system [4].

High impact information on dibenzofuran

• During the past decade it has been shown conclusively that the incineration of municipal and industrial wastes gives rise to emissions of chlorinated dibenzodioxins and dibenzofurans [5].
• Comparative toxicology and mechanism of action of polychlorinated dibenzo-p-dioxins and dibenzofurans [6].
• We measured the blood serum levels of polychlorinated dibenzo-p-dioxins and dibenzofurans, which were substituted with chlorine at the 2,3,7,8 position, in the nine pesticide applicators and in a matched group of nine control subjects [7].
• Semen quality after prenatal exposure to polychlorinated biphenyls and dibenzofurans [8].
• 6DBF7 is composed of a beta-sheet-inducing dibenzofuran (DBF)-turn mimetic and two short key amino acid sequences from anginex [9].

Chemical compound and disease context of dibenzofuran

• The bacterium Sphingomonas sp. strain RW1 is able to use dibenzo-p-dioxin, dibenzofuran, and several hydroxylated derivatives as sole sources of carbon and energy [10].
• The first step in the degradation of dibenzofuran and dibenzo-p-dioxin by Sphingomonas sp. strain RW1 is carried out by dioxin dioxygenase (DxnA1A2), a ring-dihydroxylating enzyme [11].
• The resultant strain, Rhodococcus erythropolis XPDN, could simultaneously transform the model pollutants dibenzothiophene, carbazole, and dibenzofuran to nontoxic metabolites and may have an application potential for bioremediation [12].
• 3-(2-hydroxyphenyl)catechol as substrate for proximal meta ring cleavage in dibenzofuran degradation by Brevibacterium sp. strain DPO 1361 [13].
• Key words: breast neoplasm, carcinogenic marker, estrogen catabolism, estrogen metabolism, polychlorinated biphenyls, polychlorinated dibenzodioxins, polychlorinated dibenzofurans [14].

Biological context of dibenzofuran

• This article reviews the present state of the art regarding the toxicokinetics and metabolism of polychlorinated dibenzo-p-dioxins (PCDDs) and dibenzofurans (PCDFs) [15].
• For enzyme induction, the CoMFA-derived QSARs were highly predictive for the dibenzofurans but were only partially successful for the dioxins [16].
• Intake, fecal excretion, and body burden of polychlorinated dibenzo-p-dioxins and dibenzofurans in breast-fed and formula-fed infants [17].
• Structure-activity relationships for the toxicity of polychlorinated dibenzofurans: approach through density functional theory-based descriptors [18].
• Biologic and toxic effects of polychlorinated dibenzo-p-dioxin and dibenzofuran congeners in the guinea pig. Quantitative structure-activity relationships [19].

Anatomical context of dibenzofuran

• Methods for the quantitative determination of multiple, specific polychlorinated dibenzo-p-dioxin and dibenzofuran isomers in human adipose tissue in the parts-per-trillion range. An interlaboratory study [20].
• This article on PBDEs is an extension of our previous studies on concentrations of dioxins, dibenzofurans, polychlorinated biphenyls, and other chlorinated organic compounds in human milk in a number of countries [21].
• An international workshop reviewed 20 ongoing or recently completed studies of the effects of perinatal exposures to dioxins, dibenzofurans, and PCBs on the reproductive, endocrine, neurodevelopmental, and immune systems [22].
• We analyzed placentas for 17 polychlorinated dibenzo-p-dioxins and dibenzofurans and 12 dioxin-like PCB congeners with the World Health Organization-defined toxic equivalent factors, and six indicator PCBs by high-resolution gas chromatography and high-resolution mass spectrometry [23].
• Recent reports have shown that alpha-naphthoflavone (alpha-NF) in vivo enhances the sister chromatid exchange (SCE) frequency in lymphocytes from human populations exposed to cigarette smoke or polychlorinated biphenyls and dibenzofurans [24].

Associations of dibenzofuran with other chemical compounds

• Young female Long-Evans rats were dosed via gavage with 18 different polyhalogenated aromatic hydrocarbons [2 dioxins, 4 dibenzofurans, and 12 PCBs, including dioxin-like and non-dioxin-like PCBs] for 4 consecutive days [25].
• Body Burdens of Polychlorinated Dibenzo-p-dioxins, Dibenzofurans, and Biphenyls and Their Relations to Estrogen Metabolism in Pregnant Women [14].
• Brij 35 accelerated dissolution and biodegradation of solid dibenzofuran by a factor of 2 [26].
• The emissions from simulated sugarcane (Saccharum officinarum) field burns were sampled and analyzed for polychlorinated dibenzodioxins and dibenzofurans (PCDDs and PCDFs) [27].
• Toxic equivalency factors of polybrominated dibenzo-p-dioxin, dibenzofuran, biphenyl, and polyhalogenated diphenyl ether congeners based on rainbow trout early life stage mortality [28].

Gene context of dibenzofuran

• Many polycyclic aromatic hydrocarbons (PAH) such as benzo[a]pyrene, and chlorinated PAH such as polychlorinated dibenzodioxins, dibenzofurans and biphenyls induce CYP1A1 expression through activation of an endogenous protein, the Ah receptor [29].
• The AHR mRNA expression levels exhibited significant positive correlations with total TEQs and most of individual congener TEQs derived from polychorinated dibenzo-p-dioxins, dibenzofurans and non-ortho coplanar polychorinated biphenyls (PCBs), indicating the transcriptional up-regulation of AHR expression by these congeners [30].
• A number of structural analogs of TCDD, such as the polychlorinated dibenzofurans, also interact with the Ah receptor, and they produce the same spectrum of responses as TCDD in animal and cell models [31].
• These data suggest that the dibenzofuran-mediated decreases in GRc and EGF receptor binding capacities are similar to those caused by TCDD [32].
• Since kinetic stabilization of the TTR native state by interallelic trans suppression is known to ameliorate disease, there is reason to be optimistic that the dibenzofuran-based inhibitors will do the same [33].

Analytical, diagnostic and therapeutic context of dibenzofuran

• Determination of polychlorinated dibenzo-p-dioxins, dibenzofurans, and biphenyls by gas chromatography/mass spectrometry in the negative chemical ionization mode with different reagent gases [34].
• During incubation of glucose-pregrown cells with dibenzofuran, six major metabolites were detected by high-performance liquid chromatography [35].
• Southern blot hybridization analysis revealed that this type of dioxygenase gene is distributed among diverse dibenzofuran-utilizing actinomycetes [36].
• The genes responsible for angular dioxygenation of dibenzofuran in actinomycetes were cloned by using a degenerate set of PCR primers designed by using conserved sequences of the dioxygenase alpha subunit genes [36].
• Participants discussed results from laboratory animal experiments on PCBs, PBBs, dioxins, and dibenzofurans which demonstrate a common mode of toxicological action while also revealing large variations in toxicological potency both within and between these chemical families [37].

References