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PubMed2003

Efficient anaerobic whole cell stereoselective bioreduction with recombinant Saccharomyces cerevisiae.

In this study we investigate the NADPH-dependent stereoselective reduction of the bicyclic diketone bicyclo[2.2.2]octane-2,6-dione (BCO2,6D) to the chiral ketoalcohol (1R,4S,6S)-6-hydroxybicyclo[2.2.2]octane-2-one (BCO2one6ol). Our aim was to develop a whole cell batch process for reduction of carbonyl substrates with (i) a high cosubstrate yield (formed product/consumed cosubstrate) and (ii) a high conversion rate under anaerobic conditions with Saccharomyces cerevisiae as biocatalyst and glucose as cosubstrate. Five open reading frames (ORFs), YMR226c, YDR368w, YOR120w, YGL157w, and YGL039w, encoding reductases involved in the conversion of BCO2,6D were identified using cell-free extract from strains belonging to the ExClone collection (yeast ORF expression clones; ResGen, Invitrogen Corp., UK). We report the one-step purification and characterization of three major BCO2,6D reductases, YMR226cp, YDR368wp (YPR1p), and YOR120wp (GCY1p). The reductases were overexpressed under a strong constitutive promoter and the impact on cosubstrate yield, conversion time, glucose consumption rate, and reduction rate was investigated when reductases were overexpressed either alone or in combination with low phosphoglucose isomerase activity (encoded by YBR196c). Combining overexpression of BCO2,6D reductase with reduced glycolytic rate (low phosphoglucose isomerase activity) offers a fast whole cell stereoselective bioreduction system useful for facilitated anaerobic batch conversions.

Anaerobiosis↗
PubMed1996

Antigen--antibody interactions in the reverse micellar system: quenching of the fluorescence of fluorescein-labeled atrazine by antibodies against atrazine.

This work presents a new method for performing homogeneous fluoroimmunoassay in apolar organic media, quenching fluoroimmunoassay (QFIA). This method is based on utilization of the reverse micellar system of Aerosol OT (AOT) in n-octane as a medium for the analysis of compounds with low water solubility. It is shown using the system for determination of a hydrophobic pesticide atrazine as an example. The conjugate of atrazine with fluorescein (FA) serves as a label for fluorescence detection of antigen-antibody interaction in the reverse micellar system. The fluorescence quantum yield of this compound drastically depends on the micro-environment of the label in the reverse micelle system. Specifically, the binding of this conjugate with the antibodies solubilized in the reverse micelles results in fluorescence quenching. We found that quenching efficiency depends on the properties of the reverse micellar system (surfactant concentration, hydration degree w0, w0 = [water]/[surfactant], etc.). The optimal conditions for quenching of FA fluorescence by antibodies in reverse micelles of AOT in n-octane are low surfactant concentration and hydration degree, allowing one to get large reversed micelles (w0 = 15-20) capable of retaining solubilized antibodies. Addition of free atrazine results in displacement of the conjugate and restoration of its fluorescence. The sensitivity of the analysis to atrazine is only 10 times less than that of the commonly used method of homogeneous immunoassay, polarization fluoroimmunoassay, in aqueous solution using the same antibodies and conjugate. The advantage of QFIA in reverse micelles is that the analyte can be added when dissolved in nonpolar organic solvent.

Animals↗
PubMed1998

A fluorometric method for measurement of peroxyl radical scavenging activities of lipophilic antioxidants.

A fluorometric method for evaluation of activities of lipophilic antioxidants toward peroxyl radicals in a lipophilic medium (octane:butyronitrile; 9:1, v/v) and dioleoylphosphatidyl choline (DOPC) liposomal suspension in Tris-HCl buffer (pH 7.4 at 40 degrees C) has been developed. This fluorometric method is based on the use of the fatty acid 4,4-difluoro-5-(4-phenyl-1, 3-butadienyl)-4-bora-3a,4a-diaza-s-indacene-3-undec anoic acid (BODIPY 581/591 C11) as an indicator, 2,2'-azobis-2,4-dimethyl valeronitrile (AMVN) as a peroxyl radical generator, and 6-hydroxy-2, 5,7,8-tetramethyl chroman-2-carboxylic acid (Trolox) as a calibrator. In the absence of antioxidants, a linear correlation was found between the fluorescence decay of BODIPY 581/591 C11 and the concentration of AMVN. Trolox was used as a standard reference material for validating this newly developed method. A linear correlation was found between the net protection of the fluorescence of BODIPY 581/591 C11 and the amounts of added Trolox. Employing this method, the relative peroxyl radical scavenging activities of Trolox, alpha-tocopherol, alpha-carotene, beta-carotene, lutein, and probucol in octane:butyronitrile (9:1, v/v) were determined to be 1. 0:0.7:0.5:0.3:0.4:0.3. In the DOPC system, beta-carotene showed an antioxidant activity which is a factor of two greater than that of alpha-tocopherol. This assay is suitable for measurement of activities of antioxidants in an organic lipid environment and a liposomal medium.

Antioxidants↗
PubMed2000

The Influence of a Long-Chain Hydrocarbon on the Retention of Probes Differing in the Type of Intermolecular Interactions.

The surface properties of entirely hydroxylated, as well as significantly dehydroxylated, silica gel were investigated by means of the gas phase titration method. n-Tridecane was applied as blocking agent, while n-octane, benzene, and chloroform were the testing probes. The results obtained were compared to those from the previous investigation, where ethylmethylketone was used as blocking agent. After the proper recalculation of n-tridecane surface concentration it was stated that the titration curves for n-octane coincided for both blocking agents. The changes in nonspecific adsorption interaction do not depend on the type of the blocking agent intermolecular interactions. Copyright 2000 Academic Press.

Journal Article↗
PubMed2000

Effect of CO(2) and CHF(3) on the Solubilization of Protein in Reverse Micelles.

The effect of dissolved CO(2) and CHF(3) on the precipitation of bovine serum albumin (BSA) from reverse micelles of sodium bis(2-ethylhexyl) sulfosuccinate (AOT) in 2,2,4-trimethylpentane (iso-octane) has been studied at 308.15 K. It was found that BSA can be precipitated completely by CO(2) while the AOT and water remain in the iso-octane continuous phase. This opens up a possibility for recovery of protein solids directly from reverse micellar solutions. CHF(3) is also an effective agent for precipitation of BSA in the reverse micelles when the expansion coefficient of CHF(3) exceeds 0.4. However, the condition required for complete removal of the BSA using CHF(3) results in some precipitation of AOT and water from the solution. Copyright 2000 Academic Press.

Journal Article↗
PubMed1989

The in vitro effects of alkanes, alcohols, and ketones on rat lung cytochrome P450-dependent alkoxyphenoxazone dealkylase activities.

The sensitivities of cytochrome P450 (EC 1.14.14.1)-dependent benzyloxy- and ethoxyphenoxazone dealkylase (BzOPh'ase and EtOPh'ase, respectively) activities towards a series of aliphatic hydrocarbons were measured in the microsomal fraction of lung obtained from beta-naphthoflavone-treated rats. The unsubstituted hydrocarbons were straight-chain (n-hexane through n-undecane) and branch-chain (eight carbons). The substituted compounds were alcohols and ketones of hexane and octane. The data are expressed as I50 values, i.e. the hydrocarbon concentration required to cause 50% decrease in the rate of enzyme-catalyzed product (resorufin) formation. The unsubstituted aliphatic hydrocarbons exhibited I50 values towards BzOPh'ase from 0.76 microM (2,5-dimethylhexane) to 8.8 microM (n-hexane). The lung EtOPh'ase activity was insensitive towards the tested unsubstituted aliphatic hydrocarbons. When the alcohols and ketones of hexane and octane were tested against lung BzOPh'ase activity, I50 values ranged from 16 microM (1-octanol) to 4.8 mM (2,5-hexanedione). Lung EtOPh'ase activity exhibited some sensitivity towards the alcohols and ketones, and I50 values ranged from 0.52 mM (4-octanol) to 40.5 mM (2-hexanol). The data show rat lung BzOPh'ase and EtOPh'ase activities are differentially sensitive towards the selected unsubstituted aliphatic hydrocarbons and corresponding alcohols and ketones. The difference in sensitivities may reflect different requirements for an adventitious interaction between a hydrocarbon and enzyme active site.

Alcohols↗
PubMed1976

Acute toxicity of bicyclic phosphorus esters.

The acute toxicity of 4-ethyl-1-phospha-2,6,7-trioxabicyclo (2.2.2) octane-1-oxide and 4-ethyl-1-phospha-2,6,7-trioxabicyclo (2.2.2) octane has been determined by different routes of application in various species of animals. The compounds stimulate the activity of the central nervous system and are highly toxic. They showed no toxic cumulative effects. The presence of the bicyclic phosphate ester in the combustion products of specific rigid polyurethane foams is discussed. The question is raised whether there may be an additional hazard caused by this combustion product in a real fire situation.

Aerosols↗
PubMed1988

Utilization of phenol by hydrocarbon assimilating yeasts.

77 Ascomycetous, basidiomycetous as well as imperfect yeast strains of 46 different species and 20 genera were tested for growth with the substrates n-octane, n-hexadecane, and phenol. Of 59 yeast strains with ascomycetous cell wall structure 33 grew on hydrocarbons and 32 on phenol. No yeast strain out of 26 which are unable to use n-alkanes as a source of carbon and energy grew on phenol. In comparison with the latter 32 out of 33 n-hexadecane assimilating yeasts were also capable of using phenol. All n-octane utilizing yeasts of this group also assimilate phenol as a carbon source for growth. The correlation of the hydrocarbon assimilation with the phenol assimilation seems to be not so strong in the basidiomycetous yeasts. 7 out of 18 strains from this group grew on n-hexadecane and 13 on phenol. Furthermore, it could be shown that the use of hydrocarbons and phenol (as well as methanol) is strongly correlated with the coenzyme Q structure of the respective yeast strain. The results are discussed with respect to the particular chemical properties of the substrates used and the fact that coenzyme Q structure is considered to be an important marker of evolutionary relationships among yeasts.

Basidiomycota↗
PubMed1996

The utility of volatile hydrocarbon analysis in cases of carbon monoxide poisoning.

A new approach to investigate the circumstances relating to carbon monoxide intoxication by analysing volatile hydrocarbons in the blood of cadavers is reported. Headspace gas chromatography/mass spectrometry was used to demonstrate the hydrocarbons. The results can be characterized into four categories depending on the compounds detected. In construction fire cases where no accelerants were found at the scene benzene, toluene and styrene were detected in the blood. In cases where gasoline was found in the fire debris surrounding the victim, high levels of benzene, toluene, ethylbenzene, xylene isomers, n-hexane and n-heptane were detected in the blood. In cases where kerosene was found in the fire debris around the victim, benzene, toluene, ethylbenzene, xylene isomers, C9-aromatics(n-propylbenzene, trimethyl-benzene isomers), n-octane, n-nonane and n-decane were detected in the blood. In cases where the victim was found inside a gasoline-fuelled automobile filled with exhaust gas, benzene, toluene, ethylbenzene, xylene isomers, C9-aromatics were found, but no aliphatic hydrocarbons such as components of petroleum. The analyses of the combustion gases of inflammable materials, exhaust gas, gasoline vapours and kerosene vapours were also performed to evaluate the results of the blood analyses. Consequently, some compounds are proposed as indicators to discriminate between inhaled gases i.e. styrene in common combustion gas, n-hexane and n-heptane as well as benzene, toluene and C9-aromatics in gasoline cases, n-nonane and n-octane as well as benzene, toluene and C9-aromatics in kerosene cases, and benzene, toluene, C9-aromatics but no aliphatic hydrocarbons in exhaust gas cases.

Autopsy↗
PubMed1998

Structure-activity relationship of fluoroquinolone in Escherichia coli.

Structure-activity relationship of 20 fluoroquinolones was studied using the susceptible and 4 resistant Escherichia coli which were developed against 4 fluoroquinolones [ciprofloxacin (1), KR-10755 (6), norfloxacin (2), and ofloxacin (3)] in our laboratory. The C-7 and C-8 substituents of fluoroquinolone were important in various functions such as the inhibitory activity on DNA gyrase, permeability, and efflux. Among 20 fluoroquinolones, compounds with a 3-methyl-3,7-diazabicyclo[3.3.0]octan-1(5)-ene-7-yl substituent at the C-7 position or a chlorine substituent at the C-8 position showed a good inhibitory activity on DNA gyrase (especially a mutated DNA gyrase). Compounds with a 3,7-diazabicyclo [3.3.0]octan-1(5)-ene-7-yl substituent at the C-7 position showed good permeability in the susceptible and resistant strains, while compounds with a fluorine substituent at the C-8 position were less effluxed from cells.

Anti-Infective Agents↗
PubMed2001

Heteropteran chemical repellents identified in the citrus odor of a seabird (crested auklet: Aethia cristatella): evolutionary convergence in chemical ecology.

The exogenous application of chemical repellents is widespread in birds, but endogenous production is exceedingly rare. We herein report a new class of avian defensive compounds isolated from the feathers and volatile odor of the crested auklet (Aethia cristatella). Mass spectra indicate that n-hexanal, n-octanal, n-decanal, Z-4-decenal and a 12-carbon unsaturated aldehyde comprise the auklet odorant. Octanal and hexanal are also secreted in the repugnant metasternal gland emissions of heteropteran insects and are known to be potent invertebrate repellents. We suggest that the auklet odorant functions as an ectoparasite repellent and a signal of mate quality. This would represent a rare and direct link between vigor, quality and parasite resistance, one of several putative bases for mate selection. This is the first report of defensive compounds produced by a seabird or colonial bird and one of the few examples of chemical defense in a polar or subpolar marine vertebrate.

Animals↗
PubMed2002

An improved stereoselective reduction of a bicyclic diketone by Saccharomyces cerevisiae combining process optimization and strain engineering.

The stereoselective reduction of the bicyclic diketone bicyclo[2.2.2]octane-2,6-dione, to the ketoalcohol (1R,4S,6S)-6-hydroxybicyclo[2.2.2]octane-2-one, was used as a model reduction to optimize parameters involved in NADPH-dependent reductions in Saccharomyces cerevisiae with glucose as co-substrate. The co-substrate yield (ketoalcohol formed/glucose consumed) was affected by the initial concentration of bicyclic diketone, the ratio of yeast to glucose, the medium composition, and the pH. The reduction of 5 g l(-1) bicyclic diketone was completed in less than 20 h in complex medium (pH 5.5) under oxygen limitation with an initial concentration of 200 g l(-1) glucose and 5 g l(-1) yeast. The co-substrate yield was further enhanced by genetically engineered strains with reduced phosphoglucose isomerase activity and with the gene encoding alcohol dehydrogenase deleted. Co-substrate yields were increased 2.3-fold and 2.4-fold, respectively, in these strains.

Alcohol Dehydrogenase↗
PubMed2006

Studies of reaction parameters on synthesis of Citronellyl laurate ester via immobilized Candida rugosa lipase in organic media.

Immobilized Candida rugosa lipase was used for the synthesis of citronellyl laurate from citronellol and lauric acid. Screening of different types of support (Amberlite MB-1 and Celite) for immobilization of lipase and solvent (n-hexane, n-heptane, and iso-octane) and optimization of reaction conditions, such as catalyst loading, effect of substrates molar ratio and temperature, have been studied. The maximum enzyme activity was obtained at 310 K. The immobilized C. rugosa lipase onto Amberlite MB-1 support was found to be the best support with a conversion of 89% of citronellyl laurate ester in iso-octane compared to Celite 545. Deactivation of C. rugosa lipase at 313, 318 and 323 K were observed. Ordered bi bi mechanism with dead end complex of lauric acid was found to fit the initial rate data and the kinetic parameters were obtained by non-linear regression analysis.

Acyclic Monoterpenes↗
PubMed2006

Measurement of chemical emissions in crested auklets (Aethia cristatella).

This report presents the first quantitative estimates of emission rates for chemical signals in a bird-the crested auklet (Aethia cristatella). Volatile emissions from live birds were captured in a purified airstream onto polymer traps. Traps were eluted with methanol and analyzed with gas chromatography-mass spectrometry. The volatile collection chamber was field-calibrated with an in-line bubbler and synthetic octanal, the dominant constituent of the crested auklet's citruslike odor. The result is an index of volatile chemical emissions within a small population of wild crested auklets at Big Koniuji Island, AK, USA. The average emission rate for octanal was 5.7 micro l/50 min. Males and females did not differ in their emission rates (t ((0.05)two-tailed) = 0.44, P = 0.66). There was a sevenfold difference between minimum and maximum emission rates. Prevalence of tick infection (2%) was low despite the high abundance of ticks in the colony. The crested auklet with the lowest chemical emission rate was heavily parasitized by ticks.

Animals↗
PubMed1999

Metabolic profile of linoleic acid in stored apples: formation of 13(R)-hydroxy-9(Z),11(E)-octadecadienoic acid.

During our ongoing project on the biosynthesis of R-(+)-octane-1,3-diol the metabolism of linoleic acid was investigated in stored apples after injection of [1-14C]-, [9,10,12,13-3H]-,13C18- and unlabeled substrates. After different incubation periods the products were analyzed by gas chromatography-mass spectroscopy (MS), high-performance liquid chromatography-MS/MS, and HPLC-radiodetection. Water-soluble compounds and CO2 were the major products whereas 13(R)-hydroxy- and 13-keto-9(Z),11(E)-octadecadienoic acid, 9(S)-hydroxy- and 9-keto-10(E),12(Z)-octadecadienoic acid, and the stereoisomers of the 9,10,13- and 9,12,13-trihydroxyoctadecenoic acids were identified as the major metabolites found in the diethyl ether extracts. Hydroperoxides were not detected. The ratio of 9/13-hydroxy- and 9/13-keto-octadecadienoic acid was 1:4 and 1:10, respectively. Chiral phase HPLC of the methyl ester derivatives showed enantiomeric excesses of 75% (R) and 65% (S) for 13-hydroxy-9(Z),11(E)-octadecadienoic acid and 9-hydroxy-10(E),12(Z)-octadecadienoic acid, respectively. Enzymatically active homogenates from apples were able to convert unlabeled linoleic acid into the metabolites. Radiotracer experiments showed that the transformation products of linoleic acid were converted into (R)-octane-1,3-diol. 13(R)-Hydroxy-9(Z),11(E)-octadecadienoic acid is probably formed in stored apples from 13-hydroperoxy-9(Z),11(E)-octadecadienoic acid. It is possible that the S-enantiomer of the hydroperoxide is primarily degraded by enzymatic side reactions, resulting in an enrichment of the R-enantiomer and thus leading to the formation of 13(R)-hydroxy-9(Z),11(E)-octadecadienoic acid.

Chromatography, High Pressure Liquid↗
PubMed1991

Sequence analysis of end-labeled DNA fragments by solvolysis in aqueous solutions of different amines.

Cleavage of 3'-end-labeled DNA in hot aqueous solutions of different amines is comparatively examined for overall rate of DNA scission as well as for potential differences in the preference of the various amines for cleavage at the different bases. Under comparable conditions (0.5 M amine, 0.3 M NaCl, 90 degrees C), piperidine, diethylamine, morpholine, and ethylenediamine produce the same set of labeled fragments, at approximately equal overall cleavage rates. The same set of fragments is also obtained with diisopropylamine, triethylamine, and 1,4-diazabicyclo[2.2.2]octane, but at markedly lower overall cleavage rates. Solvolysis in aqueous piperidine or aqueous diethylamine leads to DNA scission predominantly at A sites, followed by G and C sites, and least frequently at T sites. In contrast, morpholine, ethylenediamine, diisopropylamine, triethylamine, and diazabicyclo[2.2.2]octane cleave the DNA predominantly at G sites. Therefore, use of one of the latter amines allows clear distinction of G bands and C bands, which could not be distinguished by the criterion of band intensity in the original one-lane sequencing method based on cleavage in hot aqueous piperidine (B. Ambrose and R. Pless (1985) Biochemistry 24, 6194-6200). The effect of varying the salt concentration on the cleavage distribution obtained with various amines is also examined, and a rationale is given for the influence of salt concentration and amine basicity on the relative rate of cleavage at G sites.

Amines↗
PubMed1976

Ferrous ion-mediated cytochrome P-450 degradation and lipid peroxidation in adrenal cortex mitochondria.

The relationship between the degradation reaction of cytochrome P-450 and lipid peroxidation was studied utilizing bovine adrenal cortex mitochondria. The two reactions were found to be closely correlated in terms of their response to storage of the mitochondrial preparation, stimulation by Fe2+, inhibition by EDTA and their initiation by cumene hydroperoxide. Both reactions were also found not to be inhibited by catalase, superoxide dismutase, 1,4-diazabicyclo-(2,2,2)-octane and alcohols, indicating that H2O2, superoxide, singlet oxygen and hydroxyl radicals do not participate in these reactions. Yet, diphenylamine proved to be a powerful inhibitor for both reactions, suggesting the involvement of a radical species. Cumene hydroperoxide could induce these two reactions at below 0.1 mM concentrations in the presence of molecular oxygen. The chemiluminescence observed during the Fe2+-mediated lipid peroxidation reaction which was not inhibited by either superoxide dismutase or 1,4-diazabicyclo-(2,2,2)-octane, was biphasic: one was a rapid burst; and the other was a slowly increasing emission. The latter portion of the emission of light coincided with the formation of malondialdehyde. These results indicate that in adrenal cortex mitochondria the degradation of cytochrome P-450 is closely related to lipid peroxidation.

Adrenal Cortex↗
PubMed1992

Critical factors affecting the permeabilization of Drosophila embryos by alkanes.

Because of waxes in the vitelline membrane, the Drosophila egg is effectively impermeable to liquid water and to aqueous solutes, and consequently it cannot be cryopreserved unless it can be permeabilized. The more successful of the few published permeabilization procedures involve the removal of the chorion mechanically or by hypochlorite solution, the removal of all surrounding water by air drying or alcohol, the exposure of eggs to pure alkanes like octane or hexane for some 30 s, the removal of the alkane and the transfer of the eggs to aqueous culture medium without their desiccation, and lastly incubation of the permeabilized embryos under mineral oil. In following these procedures we opted for a somewhat different approach to applying hypochlorite, water, alcohol, and alkane; namely, eggs were placed between two Nucleopore filters, and the fluids drawn sequentially through the filters by vacuum. Extensive initial attempts were mystifying and discouraging in that although permeabilization was good, survivals were poor, and modifications that increased the latter reduced the former. The explanation turned out to be that permeabilization and survival depended critically on the amount of carry-over alcohol that contaminated the alkane. To determine the effects of alcohol concentration in the alkane, it was essential first to effectively eliminate carry-over contamination and then re-add precise amounts of alcohol (isopropanol) to the alkane (n-hexane, heptane, or octane). When the alcohol concentration is less than or equal to 0.2%, permeabilization is poor; when it is greater than or equal to 0.5%, permeabilization is good but survival (hatching) is poor. There are strong interactions between alcohol concentration and exposure time to alkane/alcohol mixtures with respect to the fraction of embryos that become permeabilized and the percentage that survive. There are also significant but less critical effects from the type of alcohol and alkane. The best results for 12-h embryos (greater than or equal to 90% permeabilization and 70-80% hatching) were achieved with eggs exposed to 0.3 or 0.4% 1-butanol in n-heptane for 90 s. High survivals of permeabilized 12-h embryos did not require incubation under mineral oil. Permeabilized embryos are permeable to water, ethylene glycol, glycerol, and the stain rhodamine B (which was used to assess permeabilization). They are effectively impermeable to sucrose. Embryo age is important. Between 14 and 16 h the above permeabilization procedures become dramatically less effective.(ABSTRACT TRUNCATED AT 400 WORDS)

Air↗