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Chemical Compound Review

AC1LAZ8L     fluorene

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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


Chemical compound and disease context of fluorene


Biological context of fluorene


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].


  1. Antiviral effects of amino acid derivatives with the fluorene substituent on murine leukemia viruses. Fujita, H., Toyoshima, S. J. Natl. Cancer Inst. (1983) [Pubmed]
  2. Polyfluorenes with polyphenylene dendron side chains: toward non-aggregating, light-emitting polymers. Setayesh, S., Grimsdale, A.C., Weil, T., Enkelmann, V., Müllen, K., Meghdadi, F., List, E.J., Leising, G. J. Am. Chem. Soc. (2001) [Pubmed]
  3. Evidence for a novel pathway in the degradation of fluorene by Pseudomonas sp. strain F274. Grifoll, M., Selifonov, S.A., Chapman, P.J. Appl. Environ. Microbiol. (1994) [Pubmed]
  4. New metabolites in the degradation of fluorene by Arthrobacter sp. strain F101. Casellas, M., Grifoll, M., Bayona, J.M., Solanas, A.M. Appl. Environ. Microbiol. (1997) [Pubmed]
  5. Raman spectroscopy of a coal liquid shows that fluorescence interference is minimized with ultraviolet excitation. Asher, S.A., Johnson, C.R. Science (1984) [Pubmed]
  6. Synthesis and energy-transfer properties of hydrogen-bonded oligofluorenes. Dudek, S.P., Pouderoijen, M., Abbel, R., Schenning, A.P., Meijer, E.W. J. Am. Chem. Soc. (2005) [Pubmed]
  7. Specificity of N-acetoxy-N-2-acetylaminofluorene-induced frameshift mutation spectrum in mismatch repair deficient Escherichia coli strains mutH, L, S and U. Granger-Schnarr, M., Daune, M.P., Fuchs, R.P. J. Mol. Biol. (1986) [Pubmed]
  8. Determination of phenolic metabolites of polycyclic aromatic hydrocarbons in human urine as their pentafluorobenzyl ether derivatives using liquid chromatography-tandem mass spectrometry. Jacob, P., Wilson, M., Benowitz, N.L. Anal. Chem. (2007) [Pubmed]
  9. Combining stir bar sorptive extraction and MEKC for the determination of polynuclear aromatic hydrocarbons in environmental and biological matrices. do Ros??rio, P.M., Nogueira, J.M. Electrophoresis (2006) [Pubmed]
  10. Directed evolution of toluene ortho-monooxygenase for enhanced 1-naphthol synthesis and chlorinated ethene degradation. Canada, K.A., Iwashita, S., Shim, H., Wood, T.K. J. Bacteriol. (2002) [Pubmed]
  11. Relationships between structure of nitrated arenes and their mutagenicity in Salmonella typhimurium; 2- and 2,7-nitro substituted fluorene, phenanthrene and pyrene. Hirayama, T., Watanabe, T., Akita, M., Shimomura, S., Fujioka, Y., Ozasa, S., Fukui, S. Mutat. Res. (1988) [Pubmed]
  12. The fluorene catabolic linear plasmid in Terrabacter sp. strain DBF63 carries the beta-ketoadipate pathway genes, pcaRHGBDCFIJ, also found in proteobacteria. Habe, H., Chung, J.S., Ishida, A., Kasuga, K., Ide, K., Takemura, T., Nojiri, H., Yamane, H., Omori, T. Microbiology (Reading, Engl.) (2005) [Pubmed]
  13. 3,4-Dihydrocoumarin hydrolase with haloperoxidase activity from Acinetobacter calcoaceticus F46. Kataoka, M., Honda, K., Shimizu, S. Eur. J. Biochem. (2000) [Pubmed]
  14. Degradation of phenanthrene, fluorene and fluoranthene by pure bacterial cultures. Weissenfels, W.D., Beyer, M., Klein, J. Appl. Microbiol. Biotechnol. (1990) [Pubmed]
  15. Conformation of the deoxydinucleoside monophosphate dCpdG modified at carbon 8 of guanine with 2-(acetylamino)fluorene. Hingerty, B., Broyde, S. Biochemistry (1982) [Pubmed]
  16. Sensor for fluorene based on the incorporation of an environmentally sensitive fluorophore proximal to a molecularly imprinted binding site. Carlson, C.A., Lloyd, J.A., Dean, S.L., Walker, N.R., Edmiston, P.L. Anal. Chem. (2006) [Pubmed]
  17. Polyethylated aromatic rings: conformation and rotational barriers of 1,2,3,4,5,6,7,8-octaethylanthracene, 1,2,3,4,6,7,8-heptaethylfluorene, and 1,2,3,4,5,6,7,8-octaethylfluorene. Marks, V., Gottlieb, H.E., Melman, A., Byk, G., Cohen, S., Biali, S.E. J. Org. Chem. (2001) [Pubmed]
  18. Biotransformation of fluorene by the fungus Cunninghamella elegans. Pothuluri, J.V., Freeman, J.P., Evans, F.E., Cerniglia, C.E. Appl. Environ. Microbiol. (1993) [Pubmed]
  19. Design, synthesis, and fluorescence studies of fluorenyl fatty acids as new depth-dependent fluorescent probes for membranes: getting over the looping-back problem. Lala, A.K., Dixit, R.R., Koppaka, V., Patel, S. Biochemistry (1988) [Pubmed]
  20. Bisphenolic compounds that enhance cell cation transport are found in commercial phenol red. Kym, P.R., Hummert, K.L., Nilsson, A.G., Lubin, M., Katzenellenbogen, J.A. J. Med. Chem. (1996) [Pubmed]
  21. A potent new beta2-adrenoceptor blocking agent. Imbs, J.L., Miesch, F., Schwartz, J., Velly, J., Leclerc, G., Mann, A., Wermuth, C.G. Br. J. Pharmacol. (1977) [Pubmed]
  22. A colorimetric-enzymatic microassay for the quantitation of antibody-dependent complement activation. Montaño, R.F., Morrison, S.L. J. Immunol. Methods (1999) [Pubmed]
  23. Modulation of estrogen receptor-dependent reporter construct activation and G0/G1-S-phase transition by polycyclic aromatic hydrocarbons in human breast carcinoma MCF-7 cells. Vondrácek, J., Kozubík, A., Machala, M. Toxicol. Sci. (2002) [Pubmed]
  24. Fluorenyl fatty acids as fluorescent probes for depth-dependent analysis of artificial and natural membranes. Lala, A.K., Koppaka, V. Biochemistry (1992) [Pubmed]
  25. Remarkable interplay of redox states and conformational changes in a sterically crowded, cross-conjugated tetrathiafulvalene vinylog. Amriou, S., Perepichka, I.F., Batsanov, A.S., Bryce, M.R., Rovira, C., Vidal-Gancedo, J. Chemistry (Weinheim an der Bergstrasse, Germany) (2006) [Pubmed]
  26. Novel carbazole/fluorene hybrids: host materials for blue phosphorescent OLEDs. Shih, P.I., Chiang, C.L., Dixit, A.K., Chen, C.K., Yuan, M.C., Lee, R.Y., Chen, C.T., Diau, E.W., Shu, C.F. Org. Lett. (2006) [Pubmed]
  27. Amorphous iridium complexes for electrophosphorescent light emitting devices. Ostrowski, J.C., Robinson, M.R., Heeger, A.J., Bazan, G.C. Chem. Commun. (Camb.) (2002) [Pubmed]
  28. Annual variation of polycyclic aromatic hydrocarbon concentrations in precipitation collected near the great lakes. Sun, P., Backus, S., Blanchard, P., Hites, R.A. Environ. Sci. Technol. (2006) [Pubmed]
  29. Base pair substitution and frameshift mutagenesis induced by apurinic sites and two fluorene derivatives in a recA441 lexA (Def) strain. Granger-Schnarr, M. Mol. Gen. Genet. (1986) [Pubmed]
  30. Twin-rotor system created on a [4]radialene frame. Kuwatani, Y., Yamamoto, G., Iyoda, M. Org. Lett. (2003) [Pubmed]
  31. Quantification of 2-hydroxyfluorene in human urine by column-switching high performance liquid chromatography with fluorescence detection. Toriba, A., Chetiyanukornkul, T., Kizu, R., Hayakawa, K. The Analyst. (2003) [Pubmed]
  32. Bioaccumulation of PAHs from creosote-contaminated sediment in a laboratory-exposed freshwater oligochaete, Lumbriculus variegatus. Hyötyläinen, T., Oikari, A. Chemosphere (2004) [Pubmed]
  33. Unexpected dipivaloylation of 9-lithiated fluorene: formation of 1-(fluoren-9-ylidene)-2,2-dimethylpropyl pivalate. Robinson, P.D., Lutfi, H.G., Hou, Y., Meyers, C.Y. Acta crystallographica. Section C, Crystal structure communications. (2000) [Pubmed]
  34. Establishment of photoaffinity label derivatives of fluorene as probes in studies of chemical carcinogenesis in mammalian cell culture. Sarrif, A.M., White, W.E., DiVito, N. Cancer Res. (1979) [Pubmed]
  35. Interaction of DNA methyltransferase with aminofluorene and N-acetylaminofluorene modified poly(dC-dG). Ruchirawat, M., Becker, F.F., Lapeyre, J.N. Nucleic Acids Res. (1984) [Pubmed]
  36. Synthesis, structure, and photophysical and electrochemical properties of a pi-stacked polymer. Nakano, T., Yade, T. J. Am. Chem. Soc. (2003) [Pubmed]
  37. Isolation and characterization of a fluorene-degrading bacterium: identification of ring oxidation and ring fission products. Grifoll, M., Casellas, M., Bayona, J.M., Solanas, A.M. Appl. Environ. Microbiol. (1992) [Pubmed]
  38. Atmospheric-pressure laser ionization: a novel ionization method for liquid chromatography/mass spectrometry. Constapel, M., Schellenträger, M., Schmitz, O.J., Gäb, S., Brockmann, K.J., Giese, R., Benter, T. Rapid Commun. Mass Spectrom. (2005) [Pubmed]
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