[Induction of microsomal monooxygenase by completely fluorinated organic compounds (review)].
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Animals↗
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Results for “Fluorine Compounds”
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The origin of stable halogenated compounds in volcanic gases.
BACKGROUND: Halogenated compounds in the atmosphere are of great environmental concern due to their demonstrated negative effect on atmospheric chemistry and climate. Detailed knowledge of the emission budgets of halogenated compounds has to be gained to understand better their specific impact on ozone chemistry and the climate. Such data are also highly relevant to guide policy decisions in connexion with international agreements about protection of the ozone layer. In selected cases, the relevance of specific emission sources for certain compounds were unclear. In this study we present new and comprehensive evidence regarding the existence and relevance of a volcanic contribution of chlorofluorocarbons (CFCs), hydrofluorocarbons (HFCs), hydrochlorofluorocarbons (HCFCs), halons (bromine containing halo(hydro)carbons), and fully fluorinated compounds (e.g. CF4 and SF6) to the atmospheric budget. METHODS: In order to obtain new evidence of a volcanic origin of these compounds, we collected repeatedly, during four field campaigns covering a period of two years, gases from fumaroles discharging over a wide range of temperatures at the Nicaraguan subduction zone volcanoes Momotombo, Cerro Negro and Mombacho, and analysed them with very sensitive GC/MS systems. RESULTS AND DISCUSSION: In most fumarolic samples certain CFCs, HFCs, HCFCs, halons, and the fully fluorinated compounds CF4 and SF6 were present above detection limits. However, these compounds occur in the fumarole gases in relative proportions characteristic for ambient air. CONCLUSION: This atmospheric fingerprint can be explained by variable amounts of air entering the porous volcanic edifices and successively being incorporated into the fumarolic gas discharges. Recommendation and Outlook. Our results suggest that the investigated volcanoes do not constitute a significant natural source for CFCs, HFCs, HCFCs, halons, CF4, SF6 and NF3.
Air Pollutants↗
Health effects of occupational exposure to fluorine and its compounds in a small-scale enterprise.
A 7-yr study was conducted to evaluate the respiratory effects of fluorine compounds on exposed workers in a small-scale enamel enterprise. Air monitoring was done and 75 pairs, exposed and non-exposed workers were examined. The applied tests were: an epidemiological questionnaire, the bronchitis record, clinical examinations and urinary fluorine. Linear regression analysis was done. The values of fluorine in the air of workplaces ranged from 0.1 to 3.7 mg/m3 air during the study. Twenty five point and seven percent of exposed workers presented chronic rhinitis, laryngotracheitis and bronchitis. The smoking habit was similar in both groups. The incidence of chronic bronchitis was significantly higher in exposed workers compared to the non-exposed ones. The values of urinary fluorine were higher in the exposed versus the control group. Linear regression analysis has shown positive correlations between the fluorine exposure and incidence of chronic bronchitis (r=0.75), as well as the incidence of chronic respiratory diseases (r=0.71). Fluorine exposure may be responsible for the high incidence of chronic irritative respiratory diseases, especially for chronic bronchitis in exposed workers. For diseases prevention it is advisable to reduce the levels of fluorine in the air of workplaces and to decrease the concentration of fluorine compounds in the composition of enamel.
Adult↗
Selective fluorination in drug design and development: an overview of biochemical rationales.
Several strategies used in the rational design and synthesis of fluorinated compounds as potential therapeutic agents are reviewed. Applications of fluorine substitution in empirical SAR studies for lead development also are discussed, along with the implications with respect to fluorine target interactions that can be derived from biological activities.
Animals↗
Evaluation of analytical methods for fluorine in biological and related materials.
During the past two decades, some major pitfalls in fluorine analysis have been recognized and overcome. Therefore, it is important that facts be separated from fallacies in published literature on levels and forms of fluorine (ionic, bound, covalent, etc.) in biological materials, in order that correct perceptions of physiological, biochemical, and toxicological aspects of inorganic as well as organic fluorine compounds can be formed. Trace amounts of inorganic fluoride in biological samples can now be accurately determined with the fluoride electrode either directly or following diffusion, adsorption, or reverse extraction of fluoride (when necessary). The aluminum monofluoride molecular absorption technique provides an excellent rapid method for determination of trace amounts of inorganic fluoride (in the absence of organic fluorine). Fluorine in most organic fluorine compounds is not available for distillation, diffusion, or reverse-extraction. The sample needs to be ashed (open ashing) or combusted (oxygen flask, oxygen bomb, pyrohydrolysis) for covalently bound fluorine to be converted to fluoride ions. This can now be readily accomplished at room temperature by the reductive cleavage of the C-F bond with the sodium biphenyl reagent. Some recommendations for future research have been made.
Animals↗
Structural micellar transition for fluorinated and hydrogenated sodium carboxylates induced by solubilization of benzyl alcohol.
The solubility of benzyl alcohol in micellar solutions of sodium octanoate and sodium perfluorooctanoate was studied. From the isotherms of specific conductivity versus molality at different alcohol concentrations, the critical micelle concentration and the degree of ionization of the micelles were determined. The cmc linearly decreases upon increasing the amount of benzyl alcohol present in aqueous solutions with two distinct slopes. This phenomenon was interpreted as a clustering of alcohol molecules above a critical point, around 0.1 mol kg(-1). Attending to the equivalent conductivity versus square root of molality, the presence of a second micellar structure for the fluorinated compound was assumed. The thermodynamic parameters associated with the process of micellization were estimated by applying Motomura's model for binary surfactant mixtures, modified by Pérez-Villar et al. (Colloid Polym. Sci 1990, 268, 965) for the case of alcohol-surfactant solutions. A comparison of the hydrogenated and fluorinated compounds was carried out and discussed.
Journal Article↗
New Fluorinated Stannic Compounds as Precursors of F-Doped SnO(2) Materials Prepared by the Sol-Gel Route.
Dialkoxydi(beta-diketonate)tin(IV) compounds react either with difluorodi(beta-diketonate)tin(IV) or with butanoyl fluoride to yield novel tin complexes Sn(OR(1))F(R(2)COCHCOR(2))(2) 1 (R(1) = tert-amyl, isopropyl, ethyl; R(2) = methyl, tert-butyl). Multinuclear (1)H, (13)C, (19)F, and (119)Sn NMR spectroscopic characterization showed that complexes 1 are octahedral in solution with a cis configuration for the fluorine and the alkoxide group. Kinetics of configurational rearrangements were studied by variable-temperature (13)C NMR spectroscopy. The hydrolytic behavior of 1 was determined for different hydrolysis ratios h = [H(2)O]/[1]. For R(1) = tert-amyl, a dimeric fluorinated species was mainly obtained for h = 0.5, and addition of 2 mol equiv of water led to a fluorinated stannic oxopolymer soluble in CH(3)CN. In the latter case, the powder obtained after solvent elimination and treatment in air at 550 degrees C consisted of crystalline SnO(2) cassiterite particles containing the required amount (3 mol %) of doping fluorine and exhibiting electronic conductivity comparable to that of Sn-doped In(2)O(3). Complexes 1 are the first precursors of F-doped SnO(2) materials prepared by the sol-gel route.
Journal Article↗
Metabolism of capecitabine, an oral fluorouracil prodrug: (19)F NMR studies in animal models and human urine.
Capecitabine (Xeloda; CAP) is a recently developed oral antineoplastic prodrug of 5-fluorouracil (5-FU) with enhanced tumor selectivity. Previous studies have shown that CAP activation follows a pathway with three enzymatic steps and two intermediary metabolites, 5'-deoxy-5-fluorocytidine (5'-DFCR) and 5'-deoxy-5-fluorouridine (5'-DFUR), to form 5-FU preferentially in tumor tissues. In the present work, we investigated all fluorinated compounds present in liver, bile, and perfusate medium of isolated perfused rat liver (IPRL) and in liver, plasma, kidneys, bile, and urine of healthy rats. Moreover, data obtained from rat urine were compared with those from mice and human urine. According to a low cytidine deaminase (3.5.4.5) activity in rats, 5'-DFCR was by far the main product in perfusate medium from IPRL and plasma and urine from rats. Liver and circulating 5'-DFCR in perfusate and plasma equilibrated at the same concentration value in the range 25 to 400 microM, which supports the involvement of es-type nucleoside transporter in the liver. 5'-DFUR and alpha-fluoro-beta-ureidopropionic acid (FUPA) + alpha-fluoro-beta-alanine (FBAL) were the main products in urine of mice, making up 23 to 30% of the administered dose versus 3 to 4% in rat. In human urine, FUPA + FBAL represented 50% of the administered dose, 5'-DFCR 10%, and 5'-DFUR 7%. Since fluorine-19 nuclear magnetic resonance spectroscopy gives an overview of all the fluorinated compounds present in a sample, we observed the following unreported metabolites of CAP: 1) 5-fluorocytosine and its hydroxylated metabolite, 5-fluoro-6-hydroxycytosine, 2) fluoride ion, 3) 2-fluoro-3-hydroxypropionic acid and fluoroacetate, and 4) a glucuroconjugate of 5'-DFCR.
Animals↗
Anaerobic degradation of fluorinated aromatic compounds.
Anaerobic enrichment cultures with sediment from an intertidal strait as inoculum were established under denitrifying, sulfate-reducing, iron-reducing and methanogenic conditions to examine the biodegradation of mono-fluorophenol and mono-fluorobenzoate isomers. Both phenol and benzoate were utilized within 2-6 weeks under all electron-accepting conditions. However, no degradation of the fluorophenols was observed within 1 year under any of the anaerobic conditions tested. Under denitrifying conditions, 2-fluorobenzoate and 4-fluorobenzoate were depleted within 84 days and 28 days, respectively. No loss of 3-fluorobenzoate was observed. All three fluorobenzoate isomers were recalcitrant under sulfate-reducing, iron-reducing, and methanogenic conditions. The degradation of the fluorobenzoate isomers under denitrifying conditions was examined in more detail using soils and sediments from different geographic regions around the world. Stable enrichment cultures were obtained on 2-fluorobenzoate or 4-fluorobenzoate with inoculum from most sites. Fluoride was released stoichiometrically, and nitrate reduction corresponded to the values predicted for oxidation of fluorobenzoate to CO2 coupled to denitrification. The 2-fluorobenzoate-utilizing and 4-fluorobenzoate-utilizing cultures were specific for fluorobenzoates and did not utilize other halogenated (chloro-, bromo-, iodo-) benzoic acids. Two denitrifying strains were isolated that utilized 2-fluorobenzoate and 4-fluorobenzoate as growth substrates. Preliminary characterization indicated that the strains were closely related to Pseudomonas stutzeri.
Anaerobiosis↗
Use of a novel fluorinated organosulfur compound to isolate bacteria capable of carbon-sulfur bond cleavage.
The vacuum residue fraction of heavy crudes contributes to the viscosity of these oils. Specific microbial cleavage of C-S bonds in alkylsulfide bridges that form linkages in this fraction may result in dramatic viscosity reduction. To date, no bacterial strains have been shown conclusively to cleave C-S bonds within alkyl chains. Screening for microbes that can perform this activity was greatly facilitated by the use of a newly synthesized compound, bis-(3-pentafluorophenylpropyl)-sulfide (PFPS), as a novel sulfur source. The terminal pentafluorinated aromatic rings of PFPS preclude growth of aromatic ring-degrading bacteria but allow for selective enrichment of strains capable of cleaving C-S bonds. A unique bacterial strain, Rhodococcus sp. strain JVH1, that used PFPS as a sole sulfur source was isolated from an oil-contaminated environment. Gas chromatography-mass spectrometry analysis revealed that JVH1 oxidized PFPS to a sulfoxide and then a sulfone prior to cleaving the C-S bond to form an alcohol and, presumably, a sulfinate from which sulfur could be extracted for growth. Four known dibenzothiophene-desulfurizing strains, including Rhodococcus sp. strain IGTS8, were all unable to cleave the C-S bond in PFPS but could oxidize PFPS to the sulfone via the sulfoxide. Conversely, JVH1 was unable to oxidize dibenzothiophene but was able to use a variety of alkyl sulfides, in addition to PFPS, as sole sulfur sources. Overall, PFPS is an excellent tool for isolating bacteria capable of cleaving subterminal C-S bonds within alkyl chains. The type of desulfurization displayed by JVH1 differs significantly from previously described reaction results.
Bacteria↗
Effect of fluorine containing compounds on the activity of glycolytic enzymes in rat hepatocytes.
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Animals↗
Biotransformation of aromatic compounds. Monitoring fluorinated analogues by NMR.
The results presented here illustrate the power of NMR in the non-invasive analysis of microbial transformations. Whilst the definitive identification of products requires purification and full structural elucidation. NMR can provide rapid insights into the nature of these reactions and their regulation in vivo. In addition, once the products have been identified NMR methods allow rapid assessment of the effects of genetic and physiological manipulation, and on competing metabolic fluxes with mixed substrates and branched pathways.
Benzene Derivatives↗
Electroytic partial fluorination of organic compounds. 52. Regio- and diastereoselective anodic fluorination of thiazolidines.
Anodic fluorination of N-benzoyl, N-acethyl-, and N-formylthiazolidine derived from L-cysteine was carried out in dimethoxyethane (DME) and acetonitrile containing various supporting fluoride salts using an undivided cell. Highly regioselective fluorination proceeded to provide the corresponding 5-monofluorinated thiazolidine derivatives in good yields in DME, and the diastereoselectivitiy was moderate to high regardless of the supporting fluoride salts. The diastereoselectivitiy of the fluorination was greatly affected by the bulkyness of the subsitituent on the nitrogen atom, and N-benzoylthiazolidine gave much higher diastereoselectivity compared with N-formyl derivative. The fluorination of the thiazolidines was not achieved by commercially available fluorinating reagents such as N-fluoropyridinium salts.
Electrochemistry↗
Fluorinated heterocyclic compounds. An expedient route to 5-perfluoroalkyl-1,2,4-triazoles via an unusual hydrazinolysis of 5-perfluoroalkyl-1,2,4-oxadiazoles: first examples of an ANRORC-like reaction in 1,2,4-oxadiazole derivatives.
The hydrazinolysis reaction of 5-perfluoroalkyl-1,2,4-oxadiazoles has been investigated. Nucleophilic addition of the reagent to the C(5)-N(4) double bond of the oxadiazole ring, followed by ring-opening and then ring-closure involving the beta-nitrogen atom of the hydrazino moiety and the C(3) of the oxadiazole ring, explains the formation of 5-perfluoroalkyl-1,2,4-triazoles as final products. Useful applications in synthesis of this uncommon hydrazinolysis can be claimed.
Journal Article↗
Synthesis of 3'-deoxy-3'-difluoromethyl azanucleosides from trans-4-hydroxy-l-proline.
[reaction: see text] Two strategies were tried to synthesize 3'-deoxy-3'-difluoromethyl azanucleosides. After the failure of the first route, the key intermediate 12 from trans-4-hydroxyproline 7 in 8 steps was stereoselectively prepared. The alcohol 12 was subjected to selective protection, oxidation, and difluoromethylenation to afford the fluorinated compound 18, whose hydrogenation was then systematically investigated. After a series of transformations of protecting groups, the resultant compounds 22 and 23 were oxidized to the desired lactams 24 and 25, which were successfully utilized to synthesize our target molecules, 3'-deoxy-3'-difluoromethyl azanucleosides 33, 34a, 34b, and 35.
Aza Compounds↗
Phase I/II study of combination therapy of oral fluorinated pyrimidine compound S-1 with low-dose cisplatin in patients with unresectable and/or recurrent advanced gastric cancer: a novel study design to evaluate safety and efficacy.
A phase I/II clinical trial has been planned to evaluate the safety and efficacy of combination therapy of S-1 with low-dose cisplatin in patients with unresectable or recurrent gastric cancer. A new statistically as well as clinically deliberated study design is applied to determine the maximal benefits of combination chemotherapy. This trial uses a 'continual reassessment method' for evaluating toxicity and a "two-stage method" for assessing the response rate to determine the combination that achieves adequate tumor response without toxicity in a high proportion of patients. Three specialized institutions will recruit 10-16 patients for the phase I part of the trial, and 14 institutions, in conjunction with the three specialized ones, will enroll 42 patients for the phase II part. The goal of this trial is to establish a useful chemotherapeutic treatment in an outpatient setting.
Administration, Oral↗
COMPLEX compounds of fluorine in caries control.
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Dental Caries↗
Synthesis, antimicrobial activity and in vivo fluorine NMR of a hexafluorinated derivative of tilmicosin.
A new fluorinated analog of tilmicosin was synthesized by the reductive amination of desmycosin with 3,5-bis(trifluoromethyl)piperidine. Despite an apparently small change in structure, the fluorinated analog had much less in vitro antimicrobial activity than tilmicosin and it failed to protect 3-day old chicks against a Pasteurella multocida challenge at 64 mg/kg sc. In a preliminary in vivo fluorine NMR experiment in a female Sprague-Dawley rat, a 19F NMR signal was detected in the liver one hour after ip administration of the fluorinated compound. Therefore, although this fluorinated derivative had less antimicrobial activity than tilmicosin, it may nevertheless provide a suitable model of tilmicosin for pharmacokinetic studies using in vivo fluorine NMR.
Animals↗