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| Fluorene , or 9H-fluorene is an organic compound with the formula (C6H4)2CH2. It forms white crystals that exhibit a characteristic, aromatic odor similar to that of naphthalene. Despite its name, it does not contain the element fluorine, but rather it comes from the violet fluorescence it exhibits. For commercial purposes it is obtained from coal tar, where it was discovered and named by Marcellin Berthelot in 1867.
It is insoluble in water and soluble in many organic solvents. Although sometimes classified as a polycyclic aromatic hydrocarbon, the five-membered ring has no aromatic properties. Fluorene is mildly acidic. |
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Read full article at Wikipedia
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| InChI=1S/C13H10/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)12/h1-8H,9H2 |
| NIHNNTQXNPWCJQ-UHFFFAOYSA-N |
| C1C2=CC=CC=C2C2=CC=CC=C12 |
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carcinogenic agent
A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
(via polycyclic arene )
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endocrine disruptor
Any compound that can disrupt the functions of the endocrine (hormone) system
(via polycyclic arene )
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View more via ChEBI Ontology
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2,2'-Methylenebiphenyl
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KEGG COMPOUND
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2,3-benzindene
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ChemIDplus
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Diphenylenemethane
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KEGG COMPOUND
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Fluoren
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ChEBI
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Fluorene
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KEGG COMPOUND
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o-biphenylenemethane
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NIST Chemistry WebBook
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o-biphenylmethane
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ChemIDplus
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6592
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ChemSpider
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9FL
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PDBeChem
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c0388
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UM-BBD
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C07715
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KEGG COMPOUND
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FDB007671
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FooDB
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Fluorene
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Wikipedia
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FLUORENE
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MetaCyc
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| View more database links |
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1363491
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Reaxys Registry Number
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Reaxys
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28451
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Gmelin Registry Number
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Gmelin
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86-73-7
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CAS Registry Number
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KEGG COMPOUND
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86-73-7
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CAS Registry Number
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ChemIDplus
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86-73-7
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CAS Registry Number
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NIST Chemistry WebBook
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Mantoku M, Ichida M, Umezu I, Sugimura A, Aoki-Matsumoto T (2017)
Lasing in organic mixed-crystal thin films with cavities composed of naturally formed cracks.
Optics letters 42, 1528-1531 [PubMed:28409789]
[show Abstract]
This study investigates the possibility that a crack pair that is naturally formed in the course of sample preparation functions as a laser cavity. Lasing with longitudinal mode structures has been reported in mixed-crystal thin films composed of fluorene and anthracene without artificial cavity structure. In the present study, it was shown that lasing is observed only when an excitation spot covers parallel pairs of cracks. The longitudinal mode intervals of the stimulated emission spectra for several crack pairs were found to be proportional to the inverse of the crack spacing. Furthermore, the interval for the artificially fabricated metal cavity followed the same linear relation. These results indicate that the crack pairs can function as laser cavities. | Tashiro S, Umeki T, Kubota R, Shionoya M (2014)
Simultaneous arrangement of up to three different molecules on the pore surface of a metal-macrocycle framework: cooperation and competition.
Angewandte Chemie (International ed. in English) 53, 8310-8315 [PubMed:24889657]
[show Abstract]
Porous crystals are excellent materials with potential spatial functions through molecular encapsulation within the pores. Co-encapsulation of multiple different molecules further expands their usability and designability. Herein we report the simultaneous arrangement of up to three different guest molecules, TTF (tetrathiafulvalene), ferrocene, and fluorene, on the pore surfaces of a porous crystalline metal-macrocycle framework (MMF). The position and orientation of adsorbed molecules arranged in the pore were determined by single-crystal X-ray diffraction analysis. The anchoring effect of hydrogen bonds between the hydroxy groups of the guest molecules and inter-guest cooperation and competition are significant factors in the adsorption behaviors of the guest molecules. This finding would serve as a design basis of multicomponent functionalized nanospaces for elaborate reactions that are realized in enzymes. | Inoue K, Usami Y, Ashikawa Y, Noguchi H, Umeda T, Yamagami-Ashikawa A, Horisaki T, Uchimura H, Terada T, Nakamura S, Shimizu K, Habe H, Yamane H, Fujimoto Z, Nojiri H (2014)
Structural basis of the divergent oxygenation reactions catalyzed by the rieske nonheme iron oxygenase carbazole 1,9a-dioxygenase.
Applied and environmental microbiology 80, 2821-2832 [PubMed:24584240]
[show Abstract]
Carbazole 1,9a-dioxygenase (CARDO), a Rieske nonheme iron oxygenase (RO), is a three-component system composed of a terminal oxygenase (Oxy), ferredoxin, and a ferredoxin reductase. Oxy has angular dioxygenation activity against carbazole. Previously, site-directed mutagenesis of the Oxy-encoding gene from Janthinobacterium sp. strain J3 generated the I262V, F275W, Q282N, and Q282Y Oxy derivatives, which showed oxygenation capabilities different from those of the wild-type enzyme. To understand the structural features resulting in the different oxidation reactions, we determined the crystal structures of the derivatives, both free and complexed with substrates. The I262V, F275W, and Q282Y derivatives catalyze the lateral dioxygenation of carbazole with higher yields than the wild type. A previous study determined the crystal structure of Oxy complexed with carbazole and revealed that the carbonyl oxygen of Gly178 hydrogen bonds with the imino nitrogen of carbazole. In these derivatives, the carbazole was rotated approximately 15, 25, and 25°, respectively, compared to the wild type, creating space for a water molecule, which hydrogen bonds with the carbonyl oxygen of Gly178 and the imino nitrogen of carbazole. In the crystal structure of the F275W derivative complexed with fluorene, C-9 of fluorene, which corresponds to the imino nitrogen of carbazole, was oriented close to the mutated residue Trp275, which is on the opposite side of the binding pocket from the carbonyl oxygen of Gly178. Our structural analyses demonstrate that the fine-tuning of hydrophobic residues on the surface of the substrate-binding pocket in ROs causes a slight shift in the substrate-binding position that, in turn, favors specific oxygenation reactions toward various substrates. | Aoki-Matsumoto T, Mizuno H, Ichida M, Ando H, Hirai T, Mizuno K (2012)
Room-temperature lasing from fluorene thin-film crystals densely doped with anthracene.
Optics letters 37, 4880-4882 [PubMed:23202077]
[show Abstract]
The potential for room-temperature lasing in densely doped organic crystals has been examined using (fluorene)0.8-(anthracene)0.2 thin crystals fabricated in a narrow gap between two quartz plates. An excitation-intensity dependence study confirms that the system shows spectral line narrowing, a super linear increase of the narrow line above threshold excitation intensity, and laser cavity modes. These results indicate that lasing has been observed in the densely doped organic crystal, which contains in-plane cavities with a length of approximately 100 μm. | Stancu MM, Grifoll M (2011)
Multidrug resistance in hydrocarbon-tolerant Gram-positive and Gram-negative bacteria.
The Journal of general and applied microbiology 57, 1-18 [PubMed:21478643]
[show Abstract]
New Gram-positive and Gram-negative bacteria were isolated from Poeni oily sludge, using enrichment procedures. The six Gram-positive strains belong to Bacillus, Lysinibacillus and Rhodococcus genera. The eight Gram-negative strains belong to Shewanella, Aeromonas, Pseudomonas and Klebsiella genera. Isolated bacterial strains were tolerant to saturated (i.e., n-hexane, n-heptane, n-decane, n-pentadecane, n-hexadecane, cyclohexane), monoaromatic (i.e., benzene, toluene, styrene, xylene isomers, ethylbenzene, propylbenzene) and polyaromatic (i.e., naphthalene, 2-methylnaphthalene, fluorene) hydrocarbons, and also resistant to different antimicrobial agents (i.e., ampicillin, kanamycin, rhodamine 6G, crystal violet, malachite green, sodium dodecyl sulfate). The presence of hydrophilic antibiotics like ampicillin or kanamycin in liquid LB-Mg medium has no effects on Gram-positive and Gram-negative bacteria resistance to toxic compounds. The results indicated that Gram-negative bacteria are less sensitive to toxic compounds than Gram-positive bacteria, except one bacteria belonging to Lysinibacillus genus. There were observed cellular and molecular modifications induced by ampicillin or kanamycin to isolated bacterial strains. Gram-negative bacteria possessed between two and four catabolic genes (alkB, alkM, alkB/alkB1, todC1, xylM, PAH dioxygenase, catechol 2,3-dioxygenase), compared with Gram-positive bacteria (except one bacteria belonging to Bacillus genus) which possessed one catabolic gene (alkB/alkB1). Transporter genes (HAE1, acrAB) were detected only in Gram-negative bacteria. | Whitehouse CJ, Yang W, Yorke JA, Rowlatt BC, Strong AJ, Blanford CF, Bell SG, Bartlam M, Wong LL, Rao Z (2010)
Structural basis for the properties of two single-site proline mutants of CYP102A1 (P450BM3).
Chembiochem : a European journal of chemical biology 11, 2549-2556 [PubMed:21110374]
[show Abstract]
The crystal structures of the haem domains of Ala330Pro and Ile401Pro, two single-site proline variants of CYP102A1 (P450(BM3)) from Bacillus megaterium, have been solved. In the A330P structure, the active site is constricted by the relocation of the Pro329 side chain into the substrate access channel, providing a basis for the distinctive C-H bond oxidation profiles given by the variant and the enhanced activity with small molecules. I401P, which is exceptionally active towards non-natural substrates, displays a number of structural similarities to substrate-bound forms of the wild-type enzyme, notably an off-axial water ligand, a drop in the proximal loop, and the positioning of two I-helix residues, Gly265 and His266, the reorientation of which prevents the formation of several intrahelical hydrogen bonds. Second-generation I401P variants gave high in vitro oxidation rates with non-natural substrates as varied as fluorene and propane, towards which the wild-type enzyme is essentially inactive. The substrate-free I401P haem domain had a reduction potential slightly more oxidising than the palmitate-bound wild-type haem domain, and a first electron transfer rate that was about 10 % faster. The electronic properties of A330P were, by contrast, similar to those of the substrate-free wild-type enzyme. | Uchimura H, Horisaki T, Umeda T, Noguchi H, Usami Y, Li L, Terada T, Nakamura S, Shimizu K, Takemura T, Habe H, Furihata K, Omori T, Yamane H, Nojiri H (2008)
Alteration of the substrate specificity of the angular dioxygenase carbazole 1,9a-dioxygenase.
Bioscience, biotechnology, and biochemistry 72, 3237-3248 [PubMed:19060398]
[show Abstract]
Carbazole 1,9a-dioxygenase (CARDO) consists of terminal oxygenase (CARDO-O) and electron transport components. CARDO can catalyze specific oxygenation for various substrates: angular dioxygenation for carbazole and dibenzo-p-dioxin, lateral dioxygenation for anthracene, and monooxygenation for methylene carbon of fluorene and sulfide sulfur of dibenzothiophene. To elucidate the molecular mechanism determining its unique substrate specificity, 17 CARDO-O site-directed mutants at amino acid residues I262, F275, Q282, and F329, which form the substrate-interacting wall around the iron active site by CARDO-O crystal structure, were generated and characterized. F329 replacement dramatically reduced oxygenation activity. However, several mutants produced different products from the wild-type enzyme to a large extent: I262V and Q282Y (1-hydroxycarbazole), F275W (4-hydroxyfluorene), F275A (unidentified cis-dihydrodiol of fluoranthene), and I262A and I262W (monohydroxydibenzothiophenes). These results suggest the possibility that the respective substrates bind to the active sites of CARDO-O mutants in a different orientation from that of the wild-type enzyme. | Burress CN, Bodine MI, Elbjeirami O, Reibenspies JH, Omary MA, Gabbaï FP (2007)
Enhancement of external spin-orbit coupling effects caused by metal-metal cooperativity.
Inorganic chemistry 46, 1388-1395 [PubMed:17243671]
[show Abstract]
As part of our efforts to discover simple routes to room-temperature phosphors, we have investigated the interaction of bis(pentafluorophenyl)mercury (1) or trimeric perfluoro-o-phenylene mercury (2) with selected arenes (naphthalene, biphenyl, and fluorene). Solution studies indicate that 2, unlike 1, quenches the fluorescence of naphthalene. When compared to 1, the high quenching efficiency of 2 may be correlated to the higher affinity that 2 displays for arenes as well as to more acute external heavy-atom effects caused by the three mercury atoms. In the crystal, the adducts [1.naphthalene], [1.biphenyl], [1.fluorene], and [2.fluorene] form supramolecular binary stacks in which the arene approaches the mercury centers of 1 or 2 to form Hg-C pi-interactions. Analysis of the electrostatic potential surfaces of the individual components supports the involvement of electrostatic interactions. The luminescence spectra of the adducts show complete quenching of the fluorescence and display heavy-atom-induced emission whose energies and vibronic progressions correspond to the phosphorescence of the respective pure arene. The phosphorescence lifetimes are shortened by 3 or 4 orders of magnitude when compared with those of the free arenes. Taken collectively, the structural, photophysical, and computational results herein suggest that the proximity of the three mercury centers serves to enhance the Lewis acidity of 2, which becomes a better acceptor and a more effective heavy-atom effect inducer than 1. | Wang Z, Chen J, Yang P, Qiao X, Tian F (2007)
Polycyclic aromatic hydrocarbons in Dalian soils: distribution and toxicity assessment.
Journal of environmental monitoring : JEM 9, 199-204 [PubMed:17285163]
[show Abstract]
Concentrations of 15 polycyclic aromatic hydrocarbons (PAHs) were measured in surface soils collected from Dalian, China, for examination of distributions and composition profiles and their potential toxicity. The sum of 15 PAHs (SigmaPAHs) ranged from 190 to 8595 ng g(-1) dry weight, and showed an apparent urban-suburban-rural gradient in both SigmaPAHs and composition profiles. Using hierarchical cluster analysis (HCA), the sampling sites were grouped into four clusters corresponding to traffic area, park/residential area, suburban and rural areas. The ratios of naphthalene (Nap) and fluorene (Fl) versus fluoranthene (Flu), pyrene (Pyr) and indeno(1,2,3-cd)pyrene (InP) in the four clusters provided evidence of local distillation. The diagnostic ratios indicated the prevalent PAH sources were petroleum combustion and coal combustion in Dalian, and a cross plot of diagnostic ratios distinguished the urban samples from suburban and rural ones. Toxic potency assessment of soil PAHs presented a good relationship with benzo(a)pyrene (BaP) levels, toxic equivalent concentrations based on BaP (TEQ(BaP)) and dioxin-like toxic equivalent concentrations (TEQ(TCDD)). The study highlights that BaP is a good indicator for assessing the potential toxicity of PAHs, and presents a promising toxicity assessment method for soil PAHs. | Trakhtenberg LI, Fokeyev AA (2007)
Pressure and temperature dependence of H-atom tunneling in the Debye approximation. Barrier preparation and media reorganization.
The journal of physical chemistry. A 111, 9509-9515 [PubMed:17824593]
[show Abstract]
In the frame of the radiationless transitions modified theory, the analytical expression of a rate constant of the chemical reaction with an atom tunneling is found for the case of a continuous spectrum of a phonon subsystem. Two mechanisms of temperature dependence of a rate constant are taken into account, the oscillations of the potential barrier of the reaction at the intermolecular vibrations and media reorganization. The simple expressions for temperature and pressure dependencies of a rate constant are obtained in the special case of lattice motion-the Debye model. The well-known Marcus expression for the rate constant of an electron transfer in the Debye phonon spectrum is deduced first. The pressure dependence of the reorganization energy of the media is derived. Comparison of the theoretical results with the literature experimental data on H-atom tunneling in the fluorene-acridine crystal, taking into account four promotive modes (translational, librational, and two low-frequency intramolecular modes at 95 and 238 cm(-1)) and the frequency dependence of the Grueneisen parameter, is fulfilled. Good agreement of the theory and experiments is observed. | Basilevsky MV, Davidovich GV, Titov SV, Voronin AI (2006)
Non-Markovian modification of the golden rule rate expression.
The Journal of chemical physics 125, 194513 [PubMed:17129129]
[show Abstract]
The reformulation of the standard golden rule approach considered in this paper for treating reactive tunneling reduces the computation of the reaction rate to a derivation of band shapes for energy levels of reactant and product states. This treatment is based on the assumption that the medium environment is actively involved as a partner in the energy exchange with the reactive subsystem but its reorganization effect is negligible. Starting from the quantum relaxation equation for the density matrix, the required band shapes are represented in terms of the spectral density function, exhibiting the continuum spectrum inherent to the interaction between the reactants and the medium in the total reactive system. The simplest Lorentzian spectral bands, obtained under Redfield approximation, proved to be unsatisfactory because they produced a divergent rate expression at low temperature. The problem is resolved by invoking a refined spectral band shape, which behaves as Lorentzian one at the band center but decays exponentially at its tails. The corresponding closed non-Markovian rate expression is derived and investigated taking as an example the photochemical H-transfer reaction between fluorene and acridine proceeding in the fluorene molecular crystal. The kinetics in this reactive system was thoroughly studied experimentally in a wide temperature range [B. Prass et al., Ber. Bunsenges. Phys. Chem. 102, 498 (1998)]. | Marcon V, van der Vegt N, Wegner G, Raos G (2006)
Modeling of molecular packing and conformation in oligofluorenes.
The journal of physical chemistry. B 110, 5253-5261 [PubMed:16539455]
[show Abstract]
We describe the application of molecular modeling to study problems related to the packing and conformation of oligofluorene molecules in the solid state. First of all, we describe an improved force field for oligofluorenes. The model is based on the MM3 force field for the intramolecular degrees of freedom, but it relies on ab initio calculations for the torsion potential between two monomers and the electrostatic interactions. We also report ab initio calculations of the interaction potentials between fluorene and fluorenone units. The force field has been tested on the crystal structures of a fluorene monomer, a dimer, and a pentamer containing a fluorenone at the center. It has then been employed to study conformational defects of the chains, both in vacuo and in the bulk. We find that certain modes of inversion from right-handed to left-handed helices are also possible within the constraining environment of the crystals. The effect of the presence of two different types of side chains has been also addressed. Finally, the possibility of having two fluorene units parallel and close to each other has been investigated as a model of a ground-state precursor of an excimer. Our simulations show that this configuration is sterically and energetically unfavorable so that formation of an excimer following optical excitation appears to be unlikely. | Rodrigues AC, Wuertz S, Brito AG, Melo LF (2005)
Fluorene and phenanthrene uptake by Pseudomonas putida ATCC 17514: kinetics and physiological aspects.
Biotechnology and bioengineering 90, 281-289 [PubMed:15800860]
[show Abstract]
Pseudomonas putida ATCC 17514 was used as a model strain to investigate the characteristics of bacterial growth in the presence of solid fluorene and phenanthrene. Despite the lower water-solubility of phenanthrene, P. putida degraded this polycyclic aromatic hydrocarbon (PAH) at a maximum observed rate of 1.4 +/- 0.1 mg L(-1) h(-1), higher than the apparent degradation rate of fluorene, 0.8 +/- 0.07 mg L(-1) h(-1). The role of physiological processes on the biodegradation of these PAHs was analyzed and two different uptake strategies were identified. Zeta potential measurements revealed that phenanthrene-grown cells were slightly more negatively charged (-57.5 +/- 4.7 mV) than fluorene-grown cells (-51.6 +/- 4.9 mV), but much more negatively charged than glucose-grown cells (-26.8 +/- 3.3 mV), suggesting that the PAH substrate induced modifications on the physical properties of bacterial surfaces. Furthermore, protein-to-exopolysaccharide ratios detected during bacterial growth on phenanthrene were typical of biofilms developed under physicochemical stress conditions, caused by the presence of sparingly water-soluble chemicals as the sole carbon and energy source for growth, the maximum value for TP/EPS during growth on phenanthrene (1.9) being lower than the one obtained with fluorene (5.5). Finally, confocal laser microscopy observations using a gfp-labeled derivative strain revealed that, in the presence of phenanthrene, P. putida::gfp cells formed a biofilm on accessible crystal surfaces, whereas in the presence of fluorene the strain grew randomly between the crystal clusters. The results showed that P. putida was able to overcome the lower aqueous solubility of phenanthrene by adhering to the solid PAH throughout the production of extracellular polymeric substances, thus promoting the availability and uptake of such a hydrophobic compound. | Garon D, Sage L, Wouessidjewe D, Seigle-Murandi F (2004)
Enhanced degradation of fluorene in soil slurry by Absidia cylindrospora and maltosyl-cyclodextrin.
Chemosphere 56, 159-166 [PubMed:15120562]
[show Abstract]
This study investigates the fungal biodegradation of fluorene, a polycyclic aromatic hydrocarbon, in liquid medium and soil slurry. Fungal strains and cyclodextrins were used in order to degrade fluorene and optimize fluorene bioavailability and degradation in soil slurries. After a procedure of selection in solid and liquid media, maltosyl-cyclodextrin, a branched cyclodextrin was chosen. 47 fungal strains isolated from a contaminated site were tested for biodegradation. Results showed the greater efficiency of "adapted" fungi isolated from contaminated soil vs reference strains belonging to the collection of the laboratory. These assays allowed us to select the most efficient strain, Absidia cylindrospora, which was used in a bioaugmentation process. Bioaugmentation tests were performed in an artificially contaminated non-sterile soil. In the presence of A. cylindrospora, more than 90% of the fluorene was degraded within 288 h, while 576 h were necessary in the absence of fungal bioremediation. It also appeared that biodegradation was enhanced by amendment with previously selected maltosyl-cyclodextrin. The results of this study indicate that A. cylindrospora and maltosyl-cyclodextrin could be used successfully in fluorene bioremediation systems. |
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