Disease relevance of fluorene

• Antiviral effects of amino acid derivatives with the fluorene substituent on murine leukemia viruses [1].
• Two new amino acid derivatives with the fluorene substituent, when administered ip to female inbred ICR-CD1 mice inoculated with Friend murine leukemia virus, significantly inhibited virus-induced splenomegaly, reduced viable virus titers in spleen and plasma, and significantly prolonged survival time [1].
• Absorption- and emission spectra and molecular modeling confirm that the bulky dendrimer side chains do not cause extra torsion between the fluorene units [2].
• Evidence for a novel pathway in the degradation of fluorene by Pseudomonas sp. strain F274 [3].
• New metabolites in the degradation of fluorene by Arthrobacter sp. strain F101 [4].

High impact information on fluorene

• The spectra detail the presence of numerous polycyclic aromatic hydrocarbons with ring systems similar to those of naphthalene, fluorene, phenanthrene, pyrene, and triphenylene . The ultraviolet resonance Raman measurements of this highly complex sample show no significant interference from fluorescence [5].
• Energy-transfer experiments in solution and the solid state demonstrate that oligofluorenes can donate energy to a variety of energy acceptors, but that this energy transfer occurs most effectively when the donor fluorene is hydrogen-bonded to the acceptor [6].
• This fluorene derivative has been shown to induce predominantly frameshift mutations [7].
• We developed a liquid chromatography-tandem mass spectrometry method for the determination of phenolic metabolites of naphthalene, fluorene, phenanthrene, and pyrene in human urine [8].
• In this work, stir bar sorptive extraction and liquid desorption was combined with MEKC and diode-array detection (SBSE-LD-MEKC-DAD) for the determination of polynuclear aromatic hydrocarbons (PAHs) in aqueous medium, using biphenyl, fluorene, anthracene, phenanthrene, fluoranthene and pyrene as model compounds [9].

Chemical compound and disease context of fluorene

• This hypothesis was supported by the ability of E. coli expressing TOM-Green to oxidize the three-ring compounds, phenanthrene, fluorene, and anthracene faster than the wild-type enzyme [10].
• Relationships between structure of nitrated arenes and their mutagenicity in Salmonella typhimurium; 2- and 2,7-nitro substituted fluorene, phenanthrene and pyrene [11].
• The fluorene catabolic linear plasmid in Terrabacter sp. strain DBF63 carries the beta-ketoadipate pathway genes, pcaRHGBDCFIJ, also found in proteobacteria [12].
• A novel lactonohydrolase, an enzyme that catalyzes the hydrolysis of 3,4-dihydrocoumarin, was purified 375-fold to apparent homogeneity, with a 22.7% overall recovery, from Acinetobacter calcoaceticus F46, which was isolated as a fluorene-assimilating micro-organism [13].
• From these mixed cultures three pure strains were isolated: Pseudomonas paucimobilis degrading phenanthrene; P. vesicularis degrading fluorene and Alcaligenes denitrificans degrading fluoranthene [14].

Biological context of fluorene

• Conformers with the guanine-cytidine stack in which AAF does not affect base pairing place the fluorene at the Z or alternate helix exterior [15].
• Sensor for fluorene based on the incorporation of an environmentally sensitive fluorophore proximal to a molecularly imprinted binding site [16].
• Fluorene assimilation into cell biomass was estimated to be approximately 50% [3].
• MM3 calculations indicate that in the lowest energy conformation the central fluorene core of 8 adopts a twisted conformation to avoid repulsive steric interactions between the ethyls at the bay region [17].
• Biotransformation of fluorene by the fungus Cunninghamella elegans [18].

Anatomical context of fluorene

• To see the effect of attachment of a hydrophobic tail on the orientation of such fatty acids in membranes, an n-butyl group was linked to the C-7 position of fluorene in (2-fluorenyl)butyric acid to get 4-(7-n-butylfluoren-2-yl)butyric acid [19].
• When added to human fibroblasts in serum-free medium, the bisphenol fluorene derivative 9,9-bis(4'-hydroxyphenyl)-3-hydroxyfluorene (5) produced a rapid loss of K+ and a gain of Na+, at low concentrations, with an EC50 between 30 and 60 ng/mL (80-160 nM) [20].
• 1 (t-Butyl-amino-3-ol-2-propyl) oximino-9 fluorene is a new beta2-adrenoceptor blocking agent with a pA2 of 9.23+/-0.25 on isolated trachea [21].
• The assay is based on the quantitation of hemoglobin (Hb) released from lysed erythrocytes indirectly, through the generation of fluorene blue, a compound formed from 2-7 diaminofluorene in an enzymatic reaction catalyzed by the Hb molecule [22].
• In this study, several other PAHs, including fluorene, fluoranthene, pyrene, chrysene, phenanthrene and anthracene, were found to act as very weak inducers of ER-mediated activity in the MCF-7 cell line stably transfected with a luciferase reporter gene [23].

Associations of fluorene with other chemical compounds

• Long-chain acids (C4, C6, and C8) are attached to fluorene chromophore on one side, and a hydrophobic tail (C4) is attached on the other side, so that on incorporation in membranes the carboxyl end of the molecule is oriented toward the membrane-water interface and the hydrophobic tail points toward the membrane interior [24].
• The X-ray structure of the charge-transfer complex (CTC) of 10 with 2,4,5,7-tetranitrofluorene-9-dicyanomethylenefluorene (DTeF) [stoichiometry: 10(.+)(DTeF)(2) (.-)2 PhCl] reveals a twisted conformation of 10(.+) (driven by the bulky thioxanthene moiety) and provides a very rare example of segregated stacking of a fluorene acceptor in a CTC [25].
• Novel carbazole/fluorene hybrids: host materials for blue phosphorescent OLEDs [26].
• Iridium complexes with fluorene-modified phenylpyridine ligands are resistant to crystallization and can be used in the fabrication of single layer light emitting diodes [27].
• At the two Canadian sites on Lakes Huron and Ontario, lower molecular weight PAHs (e.g., fluorene to pyrene) showed long-term decreasing trends; however, no long-term trends were observed for higher molecular weight PAHs at these sites [28].

Gene context of fluorene

• Base pair substitution and frameshift mutagenesis induced by apurinic sites and two fluorene derivatives in a recA441 lexA (Def) strain [29].
• In contrast, the fluorene-substituted analogue shows a much higher rotational barrier (DeltaG() = 17.8 kcal/mol) of the butatriene bonds due to the reduced steric repulsion between the two fluorene moieties at the ground state [30].
• The 2-OHF-d9 was synthesized by the metabolism of deuterated fluorene with cytochrome P450 [31].
• Chemical analyses showed that benzo(k)fluoranthene, anthracene and fluorene were the main PAH compounds present in the tissue of oligochaetes, just as in the sediment [32].
• The protons of the tert-butyl-C=C moiety approach a proton on the fluorene ring to well within the sum of their van der Waals radii, resulting in significant molecular compression, strain and distortion [33].

Analytical, diagnostic and therapeutic context of fluorene

• Establishment of photoaffinity label derivatives of fluorene as probes in studies of chemical carcinogenesis in mammalian cell culture [34].
• Evidence that the fluorene ring is exposed is supported by circular dichroism spectra of the templates under the conditions of the assay, which indicated that the AF adducts do not appreciably change the normal B conformation of the template, while the template with 9.5% modification by AAF adducts adopted a Z form [35].
• Oligo(DBF)s having from two to eight side-chain fluorene moieties bearing different chain-terminal groups were isolated by preparative size-exclusion chromatography [36].
• During growth in the presence of fluorene, four major metabolites were detected and isolated by thin-layer chromatography and high-performance liquid chromatography [37].
• Both the effluent of an HPLC column containing a number of PAHs (benzo[a]pyrene, fluoranthene, anthracene, fluorene) and samples from direct syringe injection were analyzed with respect to selectivity and sensitivity of the overall system [38].

References