Disease relevance of phenoxybenzene

• The bacterium Sphingomonas sp. strain SS3, which utilizes diphenyl ether and its 4-fluoro, 4-chloro, and (to a considerably lesser extent) 4-bromo derivatives as sole sources of carbon and energy, was enriched from soil samples of an industrial waste deposit [1].
• Molecular cloning and expression of an Erwinia sp. gene encoding diphenyl ether cleavage in Escherichia coli [2].
• Repeated inhalation toxicity of diphenyl oxide in experimental animals [3].
• Detection of mutagenicity of diphenyl ether herbicides in Salmonella typhimurium YG1026 and YG1021 [4].
• An Acinetobacter strain PE7 with the ability to grow on salicyclic acid and to degrade diphenyl ethers was isolated from a petroleum waste pit in Louisiana. A cloned Erwinia sp. dpe gene encoding diphenyl ether cleavage was introduced into PE7 in order to enhance its degradative ability [5].

High impact information on phenoxybenzene

• Acylation stabilizes a protease-resistant conformation of protoporphyrinogen oxidase, the molecular target of diphenyl ether-type herbicides [6].
• Kinetic studies on protoporphyrinogen oxidase inhibition by diphenyl ether herbicides [7].
• With respect to the position of diphenyl ether bond between the tyrosine and dityrosine moieties, it is an isomer of isotrityrosine found in Ascaris cuticle collagen [Fujimoto et al. (1981) Biochem. Biophys. Res. Commun. 99, 637-643] [8].
• 3. Acidified chlorite split the diphenyl ether bridge of isodityrosine, and concomitantly solubilized the cell-wall glycoprotein [9].
• A chiral diphosphonite, derived from BINOL and with an achiral diphenyl ether backbone, is an excellent ligand for the Ir-catalyzed asymmetric hydrogenation of quinolines; achiral P-ligands serving as possible additives (ee = 73-96%) [10].

Chemical compound and disease context of phenoxybenzene

• The protein as expressed in E. coli is sensitive to inhibition by the diphenyl ether herbicide acifluorfen [11].
• The bacterium Sphingomonas sp. SS31, which was obtained from the diphenyl ether-degrading strain Sphingomonas sp. SS3 by an adaptation process, utilized 3-methyldiphenyl ether for growth in addition to diphenyl ether [12].
• Lithocholic acid side-chain cleavage to produce 17-keto or 22-aldehyde steroids by Pseudomonas putida strain ST-491 grown in the presence of an organic solvent, diphenyl ether [13].

Biological context of phenoxybenzene

• Characterisation of coupling products formed by biotransformation of biphenyl and diphenyl ether by the white rot fungus Pycnoporus cinnabarinus [14].
• A small volume reaction chamber coupled to a mass spectrometer was used to study the gas-phase kinetics and mechanism of the reaction of OH radicals with diphenyl ether and seven polybrominated diphenyl ethers (PBDEs) with 1-2 bromines [15].
• Immunosuppressive and monooxygenase induction activities of polychlorinated diphenyl ether congeners in C57BL/6N mice: quantitative structure-activity relationships [16].
• A commercial mixture of the brominated flame retardant pentabrominated diphenyl ether (DE-71) induces respiratory burst in human neutrophil granulocytes in vitro [17].
• The toxicology of the three commercial polybrominated diphenyl oxide (ether) flame retardants [18].

Anatomical context of phenoxybenzene

• The data suggest that thyroid hormones and derivatives have LDL-antioxidant properties, their importance being related to their 4'-hydroxy diphenyl ether structure and depending upon the nature and the position of substituents in this structure [19].
• Induction of hepatic peroxisome proliferation in mice by lactofen, a diphenyl ether herbicide [20].
• This study investigates the effects of the pentabrominated diphenyl ether mixture, DE-71, on human neutrophil granulocytes in vitro [17].
• There was no induction or inhibition of EROD in DE71 exposure to both gill epithelia and hepatocytes [21].
• Concentrations of the flame retardant 2,2',4,4'-tetrabrominated diphenyl ether (2,2',4,4'-TeBDE) in the adipose tissue of 77 individuals from Sweden were determined [22].

Associations of phenoxybenzene with other chemical compounds

• Effects of a diphenyl ether-type herbicide, chlornitrofen, and its amino derivative on androgen and estrogen receptor activities [23].
• B. subtilis protoporphyrinogen oxidase is not inhibited by the diphenyl ether herbicide acifluorfen at 100 microM and is weakly inhibited by methylacifluorfen at the same concentration [24].
• The biotransformation of biphenyl, dibenzofuran, and diphenyl ether by 24 strains belonging to 18 species of the genus Trichosporon was investigated to assess the taxonomic relevance of this property at species and genus level [25].
• Three of them were combustion processes, impurities in pentachlorophenol, and impurities in the diphenyl ether herbicide CNP [26].
• 1. Effect of the diphenyl ether herbicide fomesafen on liver preneoplastic changes and porphyrin biosynthesis was examined in male C57BL/6J mice (0.23% in the diet for 14 months) and ICR mice (0.3% in the diet for 50 weeks) [27].

Gene context of phenoxybenzene

• Cloning and characterization of the yeast HEM14 gene coding for protoporphyrinogen oxidase, the molecular target of diphenyl ether-type herbicides [28].
• It is now generally accepted that protoporphyrinogen oxidase is the target-enzyme for diphenyl-ether-type herbicides [29].
• Protoporphyrinogen oxidase (Protox), the penultimate step enzyme of the branch point for the biosynthetic pathway of Chl and hemes, is the target site of action of diphenyl ether (DPE) herbicides [30].
• The bulk lipase-catalyzed condensation reactions were feasible, but the use of diphenyl ether gave higher M(n) values (42,400 g/mol in 3 days at 70 degrees C) [31].
• The marginal increase of the inhibition constant indicates that the Val311Met point mutation in B. subtilis protoporphyrinogen oxidase may not be an important determinant in the mechanism that protects protoporphyrinogen oxidase against diphenyl ether herbicides [32].

Analytical, diagnostic and therapeutic context of phenoxybenzene

• Transmission electron microscopy (TEM) images of the single-component gels in diphenyl ether revealed that they consist of a fibrous network, while the dual-component gel presents a novel, helical, fibrous-bundle structure [33].
• In the present study, the tissue distribution of [14C]-labelled 2,2',4,4'-tetrabrominated diphenyl ether (PBDE 47) and its possible metabolites was investigated after dietary exposure in pike (Esox lucius) using whole-body autoradiography [34].
• T(3)-induced tail tip regression was antagonized by 2,2',3,3',4,4',5,5',6-nona brominated diphenyl ether (BDE206) and potentiated by hexabromocyclododecane (HBCD) in a concentration dependent manner, which was consistent with results obtained with a in vitro T(3)-dependent proliferation bioassay termed the T-screen [35].
• HPLC isolation and NMR structure elucidation of the most prominent octabromo isomer in technical octabromo diphenyl ether [36].

References