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PubMed2000

The impact of chirality of the fluorinated volatile inhalation anaesthetics on their clinical applications.

This review discusses the various chromatographic enantioseparation methods on an analytical and preparative scale for fluorinated inhalation anaesthetics used clinically, namely halothane, enflurane, desflurane and isoflurane. The differences in the pharmacodynamics and pharmacokinetics between the enantiomers of those anaesthetics are presented. It can be concluded that using a single enantiomer for these fluorinated anaesthetics is advantageous over using the racemic mixture. The racemic switch to a single enantiomer for these fluorinated volatile anaesthetics offers a more effective and safe general anaesthetic.

Anesthetics, Inhalation↗
PubMed2004

Efforts towards the design of 'teflon' proteins: in vivo translation with trifluorinated leucine and methionine analogues.

In vivo incorporation of monofluorinated noncanonical amino acids into recombinant proteins has been well-established for decades. Proteins fluorinated in this way proved to be useful tools for many practical applications. In contrast, trifluorinated amino acids have been incorporated in only a few peptides and relatively small proteins by using expression systems in living cells. A novel class of proteins with a fluorous core can be envisaged only if full replacement of the core-building hydrophobic and aliphatic amino acids such as leucine or methionine with the related analogues trifluoromethionine and trifluoroleucine would be feasible. However, our systematic efforts to introduce these amino acids in larger proteins (over 10 Da) that contain different structural motifs clearly show that only partial substitutions are possible. The reasons are high toxicity of these substances and difficulties to accommodate them into the compact cores of natural proteins without adverse effects on their structural integrity. Therefore, engineering of such three dimensional 'Teflon'-like structures would require, besides an expansion of the amino acid repertoire of the genetic code, a de novo protein design as well.

Drug Design↗
PubMed2006

Synthesis of fluoro analogues of 3,4-(methylenedioxy)amphetamine (MDA) and its derivatives.

The role of the metabolism of the entactogen 3,4-(methylenedioxy)methamphetamine (MDMA; 1b) in neurotoxic or psychopharmacologic action is widely discussed, but not yet fully understood. To prompt further investigation into the role of MDMA metabolism, six new 3,4-(difluoromethylenedioxy) analogues of MDMA (1b) were prepared and characterized. Although electronically very different, the fluoro analogues 3-5 should be sterically very similar to the non-fluorinated parent compounds. The F-atoms may prevent the formation of toxic metabolites produced via a radical pathway (Scheme 1). Different theories regarding MDMA-induced neurotoxicity are briefly reviewed and discussed. The novel compounds 3-5 may help to verify the hypothesis that MDMA-induced neurotoxicity is the result of the formation of metabolites lacking the methylenedioxy bridge.

3,4-Methylenedioxyamphetamine↗
PubMed2003

Synthesis and nonlinear optical properties of fluorine-containing naphthalocyanines.

The fluorine-containing metal naphthalocyanines [F16NcGaCl] (7) and [(F16NcGa)2O] (8), which represent the first examples of peripherally fluorine substituted naphthalocyanines, were synthesized, and the nonlinear optical transmission was studied. Peripheral substitution by fluorine atoms enhances the solubility and photostability of the naphthalocyanines. In particular, for the axially mu-oxo-bridged naphthalocyanine dimer 8, practically no aggregation was observed in organic solvents and it has proved to be an efficient optical limiter when irradiated with laser light pulses at the wavelength of 532 nm, with pulse duration of 5 ns and repetition rate of 20 Hz.

Cyanides↗
PubMed1981

Surface spectroscopic studies of Avcothane.

Avcothane is a commercially available copolymer of polyether, polyurethane, and polydimethylsiloxane; it is used primarily in aortic balloon pumps. The pumps consist of three segments which are cemented or fused together to form the balloon. The objective of this work is to characterize the surfaces, inside and outside, of the three balloon pump sections. By using x-ray photoelectron spectroscopy (ESCA), ion scattering spectroscopy (ISS), and secondary ion mass spectrometry (SIMS) a detailed analysis of the Avcothane surfaces can be performed and comparisons between various surfaces made. Previous workers have reported ESCA and Auger electron spectroscopy (AES) measurements of Avcothane and comparisons with their results will be presented. SIMS and ISS are useful analytical tools for studying polymeric biomaterials because these techniques are usually more surface sensitive than either ESCA or AES. SIMS and ISS data indicate that a thin fluorine-rich film (probably a fluorocarbon polymer) is present on the Avcothane surface. Signals from the fluorine-rich layer are more intense from the inside of the balloon pump and the intensity generally decreases from top to bottom. The outside sections of the aortic balloon pump also show the presence of fluorine, but the signals are far less intense than from the inside. One possible explanation for the fluorine-rich layer is that a fluorine-containing compound is deposited on the balloon pump during molding and preparation. Another possibility is that the layer is deposited during preparation of the Avcothane itself, but is essentially removed from the outside during sterilization.

Assisted Circulation↗
PubMed2006

Synthesis of fluorinated chitin derivatives via enzymatic polymerization.

Synthesis of fluorinated chitin derivatives has been achieved using chitinase from Bacillus sp. as a catalyst. 6'-Fluoro- (1a), 6-fluoro- (1b) and 6,6'-difluoro- (1c) chitobiose oxazoline derivatives were newly prepared as TSAS monomers for chitinase. Ring-opening polyaddition of these monomers proceeded effectively at pH 8.0-9.0 and 30-40 degrees C, giving rise to alternatingly 6-fluorinated chitin derivatives (2a and 2b) from 1a and 1b, and fully 6-fluorinated chitin derivative (2c) from 1c under total control of regioselectivity and stereochemistry. XRD measurements revealed that polysaccharides 2a and 2b had crystalline structures similar to that of alpha-chitin. [reaction: see text]

Catalysis↗
PubMed2000

Noncompetitive, reversible inhibition of aminoacylase-1 by a series of L-alpha-hydroxyl and L-alpha-fluoro fatty acids: ligand specificity of aspergillus oryzae and porcine kidney enzymes.

L-lactate and L-beta-phenyllactate have been identified in the culture broth of Streptomyces sp. KY-11 as reversible noncompetitive inhibitors of Aspergillus oryzae aminoacylase-1 and porcine kidney aminoacylase I. A series of alpha-hydroxyl acids (DL-R-CH(OH)-COOH, R = Et, n-pro, n-butyl, n-pentyl, n-hexyl) also inhibited the two enzymes in reversible noncompetitive kinetics, and the inhibition potency (-log K(i)) increased with the increased hydrophobicity of the R group. The two eukaryotic enzymes showed distinct preferences to the ligand alpha-alkyl group, and the fungus enzyme was inhibited by L-beta-phenyllactate (R = benzyl) 10(3)-fold more potently than the mammalian enzyme. L-alpha-Fluoro-beta-phenyl-propionate and its D-isomer were used to show that the L-configuration of the alpha-substituent was important for potent inhibition of both the enzymes. The fungus aminoacylase-1 steeply decreased the affinity to alpha-fluoro- and alpha-hydroxy-n-caproate as pH was raised from 7 to 11, whereas the mammalian enzyme retained the affinity to these ligands under alkaline conditions. These results suggest that A. oryzae aminoacylase-1 has an acidic residue that interacts with -OH or -F, while the mammalian enzyme would have a basic residue that recognizes the alpha-substituents.

Alkylation↗
PubMed2001

Hydroxylation of limonene enantiomers and analogs by recombinant (-)-limonene 3- and 6-hydroxylases from mint (Mentha) species: evidence for catalysis within sterically constrained active sites.

Limonene enantiomers and substrate analogs, including specifically fluorinated derivatives, were utilized to probe active site interactions with recombinant (-)-(4S)-limonene-3-hydroxylase (CYP71D13) and (-)-(4S)-limonene-6-hydroxylase (CYP71D18) from mint (Mentha) species. (-)-(4S)-Limonene is hydroxylated by both enzymes at the designated C3- and C6-allylic positions, with strict regio- and stereospecificity and without detectable allylic rearrangement, to give the corresponding products (-)-trans-isopiperitenol and (-)-trans-carveol. CYP71D13-catalyzed hydroxylation of (+)-(4R)-limonene also yields the corresponding trans-3-hydroxylated product ((+)-transisopiperitenol); however, the C6-hydroxylase converts (+)-(4R)-limonene to a completely different product profile dominated by the enantiopure cis-6-hydroxylated product (+)-cis-carveol along with several minor products, including both enantiomers of the trans-6-hydroxylated product ((+/-)-trans-carveol), indicating allylic rearrangement during catalysis. These results demonstrate that the regiospecificity and facial stereochemistry of oxygen insertion is dictated by the absolute configuration of the substrate. Fluorinated limonene analogs are also tightly bound by both enzymes and hydroxylated at the topologically congruent positions in spite of the polarizing effect of the fluorine atom on substrate reactivity. This strict retention of oxygenation geometry suggests a rigid substrate orientation imposed by multiple hydrophobic active site contacts. Structurally simplified substrate analogs are hydroxylated at slower rates and with substantial loss of regiospecificity, consistent with a loss of active site complementarity. Evaluation of the product profiles generated allowed assessment of the role of hydrophobic contacts in orienting the substrate relative to the activated oxygen species.

Catalytic Domain↗
PubMed1984

Fluosol 43 particle localization pattern in target organs of rats. An electron microscopy study.

Perfluorocarbons (PFCs), chemically inert fluorinated organic compounds with high binding capacity for O2, are under discussion as substitutes for erythrocytes. Given the paucity of E.M. observations after their use, the aim of this study was to provide more extensive ultrastructural data about PFC particle size in the emulsion and about the localization pattern in organs of rats after infusion of Fluosol 43. Attention has been focused on the particle relationships with subcellular structures and on the subsequent histopathological implications.

Animals↗
PubMed2003

Radiative forcing due to anthropogenic greenhouse gas emissions from Finland: methods for estimating forcing of a country or an activity.

The objective of this study was to assess the radiative forcing due to Finnish anthropogenic greenhouse gas emissions in three scenarios. All the Kyoto Protocol gases, i.e., CO(2), CH(4), N(2)O, and fluorinated gases, were included. The calculations showed that forcing due to Finnish emissions will increase in the case of all gases except methane by the year 2100. In 1990, radiative forcing due to Finland's emission history of all Kyoto Protocol gases was 3.2 mW/m(2), of which 71% was due to carbon dioxide, 17% to methane, and the rest to nitrous oxide. In 1990 the share of fluorinated gases was negligible. The share of methane in radiative forcing is decreasing, whereas the shares of carbon dioxide and of fluorinated gases are increasing and that of nitrous oxide remains nearly constant. The nonlinear features concerning additional concentrations in the atmosphere and radiative forcing due to emissions caused by a single country or activity are also considered. Radiative forcing due to Finnish emissions was assessed with two different approaches, the marginal forcing approach and the averaged forcing approach. The impact of the so-called background scenario, i.e., the scenario for concentration caused by global emissions, was also estimated. The difference between different forcing models at its highest was 40%, and the averaged forcing approach appeared to be the more recommendable. The effect of background concentrations in the studied cases was up to 11%. Hence, the choice of forcing model and background scenario should be given particular attention.

Carbon Dioxide↗
PubMed1994

Permeability and stability in buffer and in human serum of fluorinated phospholipid-based liposomes.

The stability (with respect to encapsulated carboxyfluorescein release) of fluorinated liposomes and their membrane permeability have been investigated in buffer and in human serum as compared to conventional hydrogenated analogues. These fluorinated liposomes are made from highly fluorinated phosphatidylcholines and contain a fluorinated core within their membrane. In buffer and in their fluid state, the fluorinated liposomes retain much more efficiently their entrapped content and display lower membrane permeability coefficients than any of their hydrogenated counterparts. This indicates that the fluorinated core acts as a very efficient barrier to permeation. In terms of molecular structure/permeability relationships, the thicker the fluorinated lipophobic core, the more efficient the barrier to permeation. In their gel state, the fluorinated core has, however, almost no effect on permeation. Interestingly, some of the 'fluid' fluorinated liposomes were even less permeable than 'gel' or 'gel-like' ones, including egg phosphatidylcholines/cholesterol liposomes. Human serum destabilizes the 'fluid' fluorinated liposomes but to a lesser extent than the 'fluid' hydrogenated ones, indicating that the fluorinated lipophobic core inside the liposomal membrane protects the vesicles, possibly by reducing their interactions with serum components. 'Gel' or 'gel-like' fluorinated liposomes are significantly more stable in serum than in buffer. They are also more stable than conventional 'gel' or 'gel-like' liposomes.

Blood↗