Disease relevance of fluorine

• The strategic value of fluorine substitution in drug design is discussed in terms of chemical structure and basic concepts in drug metabolism and drug toxicity [1].
• Myocardial viability imaging with the use of fluorine 18-fluorodeoxyglucose (FDG) PET may help to identify high-risk patients with severe left ventricular dysfunction [2].
• 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 [3].
• Monoclonal antibodies were prepared to nuclear nonhistone proteins from a 2-aminoacetyl fluorine-induced transplantable rat hepatocellular carcinoma [4].
• 19F NMR spectroscopy at 470 MHz (11.7 Tesla) has been used to directly measure the levels of 5-fluorouracil (FU) and its fluorine-containing catabolites in plasma and urine of colon cancer patients after i.v. infusion (10 min) of 60-230 mumol (8-30 mg) FU/kg, either with or without pretreatment with methotrexate (5.1-12.5 mg/kg) [5].

Psychiatry related information on fluorine

• Local cerebral uptake of deoxyglucose labeled with fluorine 18 was measured by positron emission tomography in 16 patients with schizophrenia and 11 patients with affective disorder [6].
• Brain fluoxetine measurements using fluorine magnetic resonance spectroscopy in patients with social phobia [7].
• Patients with Alzheimer's disease and multi-infarct dementia were studied with scans using fluorodeoxyglucose tagged with fluorine 18 [8].
• [Chemical reaction: see text] HOF.CH3CN, a very efficient oxygen-transfer agent made readily from fluorine and aqueous acetonitrile, was reacted with various quinoxaline derivatives to give the corresponding mono N-oxides and especially the N,N'-dioxides in very good yields under mild conditions and short reaction times [9].

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

• Twenty patients with a previous myocardial infarction underwent rest technetium-99m sestamibi imaging and positron emission tomography using fluorine (F)-18 deoxyglucose and nitrogen (N)-13 ammonia [14].
• The role of noncovalent interactions in the catalytic mechanism of the Agrobacterium faecalis beta-glucosidase was investigated by steady-state and pre-steady state kinetic analysis of the hydrolysis of a series of monosubstituted aryl glycosides, in which the hydroxyl groups on the glycone were substituted by hydrogen or fluorine [15].
• Fluorine-18-labeled androgens: radiochemical synthesis and tissue distribution studies on six fluorine-substituted androgens, potential imaging agents for prostatic cancer [16].
• Two fluorine-containing analogues of the cyclic AMP receptor protein (CRP) from Escherichia coli were prepared by biosynthetic incorporation of 5-fluorotryptophan (5-F-Trp) and 3-fluorotyrosine (3-F-Tyr) [17].
• A fluorine-containing analogue of the cyclic AMP (cAMP) receptor protein (CRP) from Escherichia coli was prepared by biosynthetic incorporation of 3-fluorophenylalanine (3-F-Phe) [18].

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

• Although both the fluorinated and unfluorinated 7,8-dihydrodiol formed from benzo(a)pyrene by liver microsomes share (R,R)-absolute configuration, the fluorinated dihydrodiol prefers the conformation in which the hydroxyl groups are pseudodiaxial due to the proximate fluorine [24].
• Imaging of fluorine and boron from fluorinated boronophenylalanine in the same cell at organelle resolution by correlative ion microscopy and confocal laser scanning microscopy [25].
• Two fluorine labels were placed on the PCC peptide; one fluorine label was placed at a MHC contact site, the other at a position involved in T-cell receptor (TCR) recognition [26].
• Effect of fluorine substitution on the interaction of lipophilic ions with the plasma membrane of mammalian cells [27].
• PURPOSE: To prospectively compare the accuracy of fluorine 18 fluorodeoxyglucose (FDG) positron emission tomography (PET) and computed tomography (CT) for detection of primary tumor and metastasis to individual lymph node groups and for nodal staging [28].

Associations of fluorine with other chemical compounds

• 12-Fluoro-5-methylchrysene, which has a fluorine atom at a peri position, is less carcinogenic toward mouse skin than is 5-methylchrysene [29].
• Substitution of fluorine at the 5-position of norepinephrine reverses the selectivity of catechol O-methyltransferase so that p-O-methylation predominates [30].
• Sorbitol biosynthesis and regulation in freeze tolerant pupae of Hyalophora cecropia have been investigated as a function of temperature by 19F and 13C nuclear magnetic resonance (NMR) spectroscopy using several 13C-labeled and/or fluorine-substituted carbohydrates [31].
• The authors used fluorine magnetic resonance spectroscopy ((19)F MRS) to evaluate age effects on whole-brain concentrations of fluvoxamine and fluoxetine in children taking SSRIs [32].
• In the course of enzymatic catalysis, the suicide substrate is activated by one- or two-electron reduction, and then a highly reactive quinone methide is generated upon elimination of the fluorine [33].

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

• Electron energy-loss spectroscopy, which apparently can detect less than 10(-20) gram of fluorine in an area of 10 square nonometers, can thus localize fluorinated tracer molecules with biological activity [39].
• Morphine-induced metabolic changes in human brain. Studies with positron emission tomography and [fluorine 18]fluorodeoxyglucose [40].
• The visualization of a covalent glycosyl enzyme intermediate by X-ray crystallography was first accomplished with a saccharide substrate substituted with fluorine at its 2-position [41].
• Rates were measured by positron emission tomography with fluorine 18-labeled fluoro-2-deoxy-D-glucose under conditions of reduced visual and auditory stimulation [42].
• In the last 26 consecutive patients, residual viability was assessed by single-photon emission computed tomography (SPECT) using fluorine (F)-18 fluorodeoxyglucose [43].

References