Disease relevance of acenaphthene

• A metabolite identified as cis-1,2-acenaphthenediol was formed from acenaphthylene by the mutant Beijerinckia sp. strain B8/36 [1].
• Novel Intermediates of Acenaphthylene Degradation by Rhizobium sp. Strain CU-A1: Evidence for Naphthalene-1,8-Dicarboxylic Acid Metabolism [2].
• Coinoculation of the mixed culture with cells of acenaphthene-grown strain Pseudomonas sp. strain A2279 mitigated the accumulation of partial transformation products and resulted in more complete degradation of acenaphthene [3].
• Functional and transcriptional analyses of the initial oxygenase genes for acenaphthene degradation from Sphingomonas sp. strain A4 [4].
• Acute and chronic life cycle toxicity of acenaphthene and 2,4,6-trichlorophenol to the midge Paratanytarsus parthenogeneticus (Diptera: Chironomidae) [5].

High impact information on acenaphthene

• The overall concentrations of acenaphthene, benzo(a)pyrene, phenanthrene, anthracene, fluoranthene, and pyrene were 526 ng/m3 air in a highly polluted urban area and 48 ng/m3 in a rural area affected by motor vehicle traffic pollution [6].
• The aromaticity of pyracylene: an experimental and computational study of the energetics of the hydrogenation of acenaphthylene and pyracylene [7].
• Piperonyl butoxide and acenaphthylene induce cytochrome P450 1A2 and 1B1 mRNA in aromatic hydrocarbon-responsive receptor knock-out mouse liver [8].
• The synthetic methodology used is based on cyclic dimerization of diastereomeric AB-type monomers 18 by a non-diastereospecific Diels-Alder reaction with isobenzofuran and acenaphthylene groups as reactive termini [9].
• Aryl hydrocarbon (Ah) receptor-independent induction of Cyp1a2 gene expression by acenaphthylene and related compounds in B6C3F1 mice [10].

Chemical compound and disease context of acenaphthene

• In contrast, acenaphthylene was oxidized to acenaphthenequinone and the compound tentatively identified as 1,2-dihydroxyacenaphthylene by the wild-type strain of Beijerinckia [1].
• For instance, the cloned genes from Pseudomonas sp. XPW-2 placed in E. coli encoded for the oxidation of such polycyclic aromatic hydrocarbons as naphthalene, biphenyl, anthracene, phenanthrene, acenaphthylene, fluorene, fluoranthene, chrysene, and pyrene [11].
• This result, and the finding that acenaphthene 1,2-imine efficiently reverts various strains of Salmonella typhimurium, demonstrates that not only K-region arene imines, but also other aziridines substituted at the two carbons with aromatic moieties, are mutagenic [12].

Biological context of acenaphthene

• Transcription of the gene cluster by ArhR was induced in the presence of acenaphthene (or its metabolite), and a putative binding site (T-N11-A motif) for ArhR was found upstream from the transcription start point of arhA3 [4].
• To isolate the genes responsible for acenaphthene degradation, transposon mutagenesis was performed on strain A4 and four mini-Tn5-inserted mutants lacking the ability to utilize acenaphthene were isolated [4].
• The products of the gas-phase reactions of acenaphthene and acenaphthylene and their fully deuterated analogues have been investigated using in situ atmospheric pressure ionization tandem mass spectrometry (API-MS) and gas chromatography-mass spectrometry (GC-MS) [13].
• By comparing PAHs with different ring structures, we have found that acenaphthylene has the highest potency to induce vasorelaxation [14].
• In the presence of NADPH, the P450 monooxygenase showed hydroxylation activity towards polycyclic aromatic hydrocarbons naphthalene, indene, acenaphthene, toluene, fluorene, m-xylene, and ethyl benzene [15].

Anatomical context of acenaphthene

• Neither the keratinocytes, fibroblasts, nor HepG2 cells were sensitive to acenaphthene [16].

Associations of acenaphthene with other chemical compounds

• The standard enthalpy of hydrogenation of acenaphthylene (1) to acenaphthene (3) at 298.15 K was determined to be minus sign(114.5 +/- 4.2) kJ x mol(-1) in toluene solution and minus sign(107.9 +/- 4.2) kJ x mol(-1) in the gas phase, by combining results of combustion and reaction-solution calorimetry [7].
• Radical-molecule reactions for aromatic growth: a case study for cyclopentadienyl and acenaphthylene [17].
• Simultaneous determination of ethylbenzene, indan, indene and acenaphthene in air by capillary gas chromatography [18].
• Application of functional group modified substrate in room-temperature phosphorescence, I--beta-cyclodextrin modified paper substrate for enrichment and determination of fluorene and acenaphthene [19].
• Plant samples were relatively enriched with low molecular weight compounds such as acenaphthene/fluorene nd phenanthrene [20].

Gene context of acenaphthene

• Further analysis revealed that the low efficacy of acenaphthylene as inducer of CYP1A1 protein and EROD activity is due to its marked cytotoxicity while no clear-cut explanation was found for the differences in efficacy between benzo[k]fluoranthene and benzo[a]pyrene [21].
• A comparison with other C(12)H(6) and C(12)H(8) isomers indicates that 2 is approximately 25 kcal/mol less stable than 1,5,9-tridehydro[12]annulene and 4 is approximately 100 kcal/mol higher in energy than acenaphthylene, both of which are synthetically accessible [22].
• The RTP signal of fluorene and acenaphthene included on the beta-CD-modified paper was increased more than 10 times compared with non-modified filter paper, indicating the formation of the inclusion complex [19].
• With the exception of acenaphthene, average concentrations of all measured PAH at BROS exceed those at EROS, with a paired t-test revealing these roadside increments to be significant (p < 0.05) for 9 out of the 16 target PAH, demonstrating the importance of traffic emissions of PAH [23].

Analytical, diagnostic and therapeutic context of acenaphthene

• In situ crystallography reveals that the solid state [2 + 2] photodimerization of acenaphthylene in a coordination cage takes place smoothly without preorganizaiton of reaction centers at a preferred geometry, because the substrate tumbles thermally in the large hollow of the cage [24].
• An attempt was made to establish a method for the simultaneous determination of ethylbenzene, indan, indene and acenaphthene by capillary gas chromatography with flame ionization detection [18].
• RT-PCR analysis suggested that a 13.5 kb gene cluster, consisting of 13 ORFs and including all the arhA genes, forms an operon, although it includes several ORFs that are apparently unnecessary for acenaphthene degradation [4].
• A novel method for the determination of fluorene and acenaphthene on solid phase extraction-room-temperature phosphorescence (SPE-RTP) was studied. beta-cyclodextrin (beta-CD) was chemically bonded onto chromatography paper by reaction with epichorohydrin in an ultrasonic bath [19].

References