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Chemical Compound Review

monofluorine     fluorine

Synonyms: fluorine(.), AC1NSEND, Fluorine atom, AG-F-55678, CHEBI:30239, ...
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Disease relevance of fluorine


Psychiatry related information on fluorine


High impact information on fluorine

  • Local cerebral uptake of deoxyglucose labeled with fluorine 18 was measured by positron-emission tomography in eight patients with schizophrenia who were not receiving medication and in six age-matched normal volunteers [10].
  • In accordance with the higher degree of disorder observed in scanning tunneling microscopy images of 1-fluorohexane, theoretical simulations show that electrostatic forces associated with the fluorine substituent are sufficiently strong to upset the delicate balance of interactions required for the formation of an ordered monolayer [11].
  • Previously, high-resolution solution (19)F NMR spectra of fluorine-labeled rhodopsin in detergent micelles were described, demonstrating the applicability of this technique to studies of tertiary structure in the cytoplasmic domain [12].
  • Our study indicates that if Mars could somehow acquire an Earth-like atmospheric composition and surface pressure, then an Earth-like temperature could be sustained by a mixture of five to seven fluorine compounds [13].
  • Delay in revascularization is associated with increased mortality rate in patients with severe left ventricular dysfunction and viable myocardium on fluorine 18-fluorodeoxyglucose positron emission tomography imaging [2].

Chemical compound and disease context of fluorine


Biological context of fluorine

  • In the last decade interactions of fluorine substituents in a variety of organic compounds have gained interest in life science and solid state materials [19].
  • Cell-mediated mutagenicity in Chinese hamster V79 cells of dibenzopyrenes and their bay-region fluorine-substituted derivatives [20].
  • Whereas the unbranched SCFA butyrate induced a more differentiated phenotype and enhanced apoptosis, two derivatives of butyrate, branched isobutyric acid and a nonmetabolizable fluorine-substituted analogue, heptafluorobutyric acid, were ineffective in inducing either differentiation or apoptosis [21].
  • The 19F NMR data for the oxidized forms of all three 2'-F-arabino-FAD proteins suggest that the fluorine experiences very similar chemical environments at the active sites [22].
  • We propose that the fluorine label in wild type citrate synthase exists in two conformational states with different mobilities, exchanging slowly on the NMR time scale, and that treatment with KCl, or truncation of the Glu-207 side chain by mutagenesis, stabilizes one of these states [23].

Anatomical context of fluorine


Associations of fluorine with other chemical compounds


Gene context of fluorine

  • In contrast, introduction of a fluorine atom preserved COX-2 potency and notably increased COX1/COX-2 selectivity [34].
  • On the other hand, alkyl chains on the sulfonamide nitrogen that contain an electron dense atom, such as a fluorine, are favored in the PNMT active site and possess little alpha2-adrenoceptor affinity, thereby conferring good selectivity (>500) [35].
  • Carbonic anhydrase inhibitors: inhibition of the tumor-associated isozyme IX with fluorine-containing sulfonamides. The first subnanomolar CA IX inhibitor discovered [36].
  • The presence of a fluorine atom in the arabinose configuration on C-2 confers resistance to solvolysis and renders the analogue less susceptible to enzymatic deamination and resistant to phosphorylytic cleavage by PNP [37].
  • A series of new, fluorine-containing substituted diphenyl sulfides was synthesized to serve as candidate ligands for positron emission tomography (PET) imaging of the serotonin transporter (SERT) and to further probe the structure-activity relationship (SAR) of this class of compounds [38].

Analytical, diagnostic and therapeutic context of fluorine


  1. Metabolism of fluorine-containing drugs. Park, B.K., Kitteringham, N.R., O'Neill, P.M. Annu. Rev. Pharmacol. Toxicol. (2001) [Pubmed]
  2. Delay in revascularization is associated with increased mortality rate in patients with severe left ventricular dysfunction and viable myocardium on fluorine 18-fluorodeoxyglucose positron emission tomography imaging. Beanlands, R.S., Hendry, P.J., Masters, R.G., deKemp, R.A., Woodend, K., Ruddy, T.D. Circulation (1998) [Pubmed]
  3. Prognostic value of pretransplantation positron emission tomography using fluorine 18-fluorodeoxyglucose in patients with aggressive lymphoma treated with high-dose chemotherapy and stem cell transplantation. Spaepen, K., Stroobants, S., Dupont, P., Vandenberghe, P., Maertens, J., Bormans, G., Thomas, J., Balzarini, J., De Wolf-Peeters, C., Mortelmans, L., Verhoef, G. Blood (2003) [Pubmed]
  4. Isolation and analysis of hepatoma nuclear proteins using monoclonal antibodies. Babin, J.K., Anderson, J.N. Cancer Res. (1988) [Pubmed]
  5. Metabolites of 5-fluorouracil in plasma and urine, as monitored by 19F nuclear magnetic resonance spectroscopy, for patients receiving chemotherapy with or without methotrexate pretreatment. Hull, W.E., Port, R.E., Herrmann, R., Britsch, B., Kunz, W. Cancer Res. (1988) [Pubmed]
  6. Anteroposterior gradients in cerebral glucose use in schizophrenia and affective disorders. Buchsbaum, M.S., DeLisi, L.E., Holcomb, H.H., Cappelletti, J., King, A.C., Johnson, J., Hazlett, E., Dowling-Zimmerman, S., Post, R.M., Morihisa, J. Arch. Gen. Psychiatry (1984) [Pubmed]
  7. Brain fluoxetine measurements using fluorine magnetic resonance spectroscopy in patients with social phobia. Miner, C.M., Davidson, J.R., Potts, N.L., Tupler, L.A., Charles, H.C., Krishnan, K.R. Biol. Psychiatry (1995) [Pubmed]
  8. The fluorodeoxyglucose 18F scan in Alzheimer's disease and multi-infarct dementia. Benson, D.F., Kuhl, D.E., Hawkins, R.A., Phelps, M.E., Cummings, J.L., Tsai, S.Y. Arch. Neurol. (1983) [Pubmed]
  9. A new efficient route for the formation of quinoxaline N-oxides and N,N'-dioxides using HOF.CH3CN. Carmeli, M., Rozen, S. J. Org. Chem. (2006) [Pubmed]
  10. Cerebral glucography with positron tomography. Use in normal subjects and in patients with schizophrenia. Buchsbaum, M.S., Ingvar, D.H., Kessler, R., Waters, R.N., Cappelletti, J., van Kammen, D.P., King, A.C., Johnson, J.L., Manning, R.G., Flynn, R.W., Mann, L.S., Bunney, W.E., Sokoloff, L. Arch. Gen. Psychiatry (1982) [Pubmed]
  11. Ultra-high vacuum scanning tunneling microscopy and theoretical studies of 1-halohexane monolayers on graphite. Müller, T., Werblowsky, T.L., Florio, G.M., Berne, B.J., Flynn, G.W. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  12. Solution 19F nuclear Overhauser effects in structural studies of the cytoplasmic domain of mammalian rhodopsin. Loewen, M.C., Klein-Seetharaman, J., Getmanova, E.V., Reeves, P.J., Schwalbe, H., Khorana, H.G. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  13. Keeping Mars warm with new super greenhouse gases. Gerstell, M.F., Francisco, J.S., Yung, Y.L., Boxe, C., Aaltonee, E.T. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  14. Positron emission tomography detects evidence of viability in rest technetium-99m sestamibi defects. Sawada, S.G., Allman, K.C., Muzik, O., Beanlands, R.S., Wolfe, E.R., Gross, M., Fig, L., Schwaiger, M. J. Am. Coll. Cardiol. (1994) [Pubmed]
  15. Mechanism of Agrobacterium beta-glucosidase: kinetic analysis of the role of noncovalent enzyme/substrate interactions. Namchuk, M.N., Withers, S.G. Biochemistry (1995) [Pubmed]
  16. Fluorine-18-labeled androgens: radiochemical synthesis and tissue distribution studies on six fluorine-substituted androgens, potential imaging agents for prostatic cancer. Liu, A., Dence, C.S., Welch, M.J., Katzenellenbogen, J.A. J. Nucl. Med. (1992) [Pubmed]
  17. 19F-n.m.r. studies of ligand binding to 5-fluorotryptophan- and 3-fluorotyrosine-containing cyclic AMP receptor protein from Escherichia coli. Sixl, F., King, R.W., Bracken, M., Feeney, J. Biochem. J. (1990) [Pubmed]
  18. 19F n.m.r. studies of conformational changes accompanying cyclic AMP binding to 3-fluorophenylalanine-containing cyclic AMP receptor protein from Escherichia coli. Hinds, M.G., King, R.W., Feeney, J. Biochem. J. (1992) [Pubmed]
  19. Fluorine in crystal engineering--"the little atom that could". Reichenbächer, K., Süss, H.I., Hulliger, J. Chemical Society reviews. (2005) [Pubmed]
  20. Cell-mediated mutagenicity in Chinese hamster V79 cells of dibenzopyrenes and their bay-region fluorine-substituted derivatives. Hass, B.S., McKeown, C.K., Sardella, D.J., Boger, E., Ghoshal, P.K., Huberman, E. Cancer Res. (1982) [Pubmed]
  21. Potentiation by specific short-chain fatty acids of differentiation and apoptosis in human colonic carcinoma cell lines. Heerdt, B.G., Houston, M.A., Augenlicht, L.H. Cancer Res. (1994) [Pubmed]
  22. Chemical modification of the N-10 ribityl side chain of flavins. Effects on properties of flavoprotein disulfide oxidoreductases. Murthy, Y.V., Massey, V. J. Biol. Chem. (1995) [Pubmed]
  23. The role of cysteine 206 in allosteric inhibition of Escherichia coli citrate synthase. Studies by chemical modification, site-directed mutagenesis, and 19F NMR. Donald, L.J., Crane, B.R., Anderson, D.H., Duckworth, H.W. J. Biol. Chem. (1991) [Pubmed]
  24. Effects of a 6-fluoro substituent on the metabolism of benzo(a)pyrene 7,8-dihydrodiol to bay-region diol epoxides by rat liver enzymes. Thakker, D.R., Yagi, H., Sayer, J.M., Kapur, U., Levin, W., Chang, R.L., Wood, A.W., Conney, A.H., Jerina, D.M. J. Biol. Chem. (1984) [Pubmed]
  25. Imaging of fluorine and boron from fluorinated boronophenylalanine in the same cell at organelle resolution by correlative ion microscopy and confocal laser scanning microscopy. Chandra, S., Kabalka, G.W., Lorey, D.R., Smith, D.R., Coderre, J.A. Clin. Cancer Res. (2002) [Pubmed]
  26. Conformational isomers of a class II MHC-peptide complex in solution. Schmitt, L., Boniface, J.J., Davis, M.M., McConnell, H.M. J. Mol. Biol. (1999) [Pubmed]
  27. Effect of fluorine substitution on the interaction of lipophilic ions with the plasma membrane of mammalian cells. Kürschner, M., Nielsen, K., von Langen, J.R., Schenk, W.A., Zimmermann, U., Sukhorukov, V.L. Biophys. J. (2000) [Pubmed]
  28. Metastasis to regional lymph nodes in patients with esophageal squamous cell carcinoma: CT versus FDG PET for presurgical detection prospective study. Yoon, Y.C., Lee, K.S., Shim, Y.M., Kim, B.T., Kim, K., Kim, T.S. Radiology. (2003) [Pubmed]
  29. Inhibition by a peri-fluorine atom of 1,2-dihydrodiol formation as a basis for the lower tumorigenicity of 12-fluoro-5-methylchrysene than of 5-methylchrysene. Amin, S., Camanzo, J., Hecht, S.S. Cancer Res. (1984) [Pubmed]
  30. Regioselectivity of catechol O-methyltransferase. The effect of pH on the site of O-methylation of fluorinated norepinephrines. Thakker, D.R., Boehlert, C., Kirk, K.L., Antkowiak, R., Creveling, C.R. J. Biol. Chem. (1986) [Pubmed]
  31. 19F and 13C NMR studies of polyol metabolism in freeze-tolerant pupae of Hyalophora cecropia. Podlasek, C.A., Serianni, A.S. J. Biol. Chem. (1994) [Pubmed]
  32. Fluorine magnetic resonance spectroscopy measurement of brain fluvoxamine and fluoxetine in pediatric patients treated for pervasive developmental disorders. Strauss, W.L., Unis, A.S., Cowan, C., Dawson, G., Dager, S.R. The American journal of psychiatry. (2002) [Pubmed]
  33. A fluoro analogue of the menadione derivative 6-[2'-(3'-methyl)-1',4'-naphthoquinolyl]hexanoic acid is a suicide substrate of glutathione reductase. Crystal structure of the alkylated human enzyme. Bauer, H., Fritz-Wolf, K., Winzer, A., Kühner, S., Little, S., Yardley, V., Vezin, H., Palfey, B., Schirmer, R.H., Davioud-Charvet, E. J. Am. Chem. Soc. (2006) [Pubmed]
  34. 4-(4-cycloalkyl/aryl-oxazol-5-yl)benzenesulfonamides as selective cyclooxygenase-2 inhibitors: enhancement of the selectivity by introduction of a fluorine atom and identification of a potent, highly selective, and orally active COX-2 inhibitor JTE-522(1). Hashimoto, H., Imamura, K., Haruta, J., Wakitani, K. J. Med. Chem. (2002) [Pubmed]
  35. Inhibitors of phenylethanolamine N-methyltransferase that are predicted to penetrate the blood-brain barrier: design, synthesis, and evaluation of 3-fluoromethyl-7-(N-substituted aminosulfonyl)-1,2,3,4-tetrahydroisoquinolines that possess low affinity toward the alpha2-adrenoceptor. Romero, F.A., Vodonick, S.M., Criscione, K.R., McLeish, M.J., Grunewald, G.L. J. Med. Chem. (2004) [Pubmed]
  36. Carbonic anhydrase inhibitors: inhibition of the tumor-associated isozyme IX with fluorine-containing sulfonamides. The first subnanomolar CA IX inhibitor discovered. Vullo, D., Scozzafava, A., Pastorekova, S., Pastorek, J., Supuran, C.T. Bioorg. Med. Chem. Lett. (2004) [Pubmed]
  37. Metabolism in human leukocytes of anti-HIV dideoxypurine nucleosides. Fridland, A., Johnson, M.A., Cooney, D.A., Ahluwalia, G., Marquez, V.E., Driscoll, J.S., Johns, D.G. Ann. N. Y. Acad. Sci. (1990) [Pubmed]
  38. Fluorinated diaryl sulfides as serotonin transporter ligands: synthesis, structure-activity relationship study, and in vivo evaluation of fluorine-18-labeled compounds as PET imaging agents. Huang, Y., Bae, S.A., Zhu, Z., Guo, N., Roth, B.L., Laruelle, M. J. Med. Chem. (2005) [Pubmed]
  39. Fluorinated molecule as a tracer: difluoroserotonin in human platelets mapped by electron energy-loss spectroscopy. Costa, J.L., Joy, D.C., Maher, D.M., Kirk, K.L., Hui, S.W. Science (1978) [Pubmed]
  40. Morphine-induced metabolic changes in human brain. Studies with positron emission tomography and [fluorine 18]fluorodeoxyglucose. London, E.D., Broussolle, E.P., Links, J.M., Wong, D.F., Cascella, N.G., Dannals, R.F., Sano, M., Herning, R., Snyder, F.R., Rippetoe, L.R. Arch. Gen. Psychiatry (1990) [Pubmed]
  41. Insights into transition state stabilization of the beta-1,4-glycosidase Cex by covalent intermediate accumulation in active site mutants. Notenboom, V., Birsan, C., Nitz, M., Rose, D.R., Warren, R.A., Withers, S.G. Nat. Struct. Biol. (1998) [Pubmed]
  42. Clinical history, brain metabolism, and neuropsychological function in Alzheimer's disease. Cutler, N.R., Haxby, J.V., Duara, R., Grady, C.L., Kay, A.D., Kessler, R.M., Sundaram, M., Rapoport, S.I. Ann. Neurol. (1985) [Pubmed]
  43. Exercise-induced ischemic arrhythmias in patients with previous myocardial infarction: role of perfusion and tissue viability. Margonato, A., Mailhac, A., Bonetti, F., Vicedomini, G., Fragasso, G., Landoni, C., Lucignani, G., Rossetti, C., Fazio, F., Chierchia, S.L. J. Am. Coll. Cardiol. (1996) [Pubmed]
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