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PubMed1982

High-performance liquid chromatographic assay of cytosolic glutathione S-transferase activity with styrene oxide.

A high-performance liquid chromatographic (HPLC) assay for measuring cytosolic glutathione S-transferase activity with styrene oxide is described. After incubating lung or liver cytosol with reduced glutathione and styrene oxide, unreacted styrene oxide is extracted into ethyl acetate. An aliquot of the aqueous phase is evaporated to dryness and reconstituted in the mobile phase for HPLC analysis. The two glutathione conjugates of styrene oxide [S-(1-phenyl-2-hydroxyethyl)glutathione and S-(2-phenyl-2-hydroxyethyl)glutathione] are separated in less than 10 min; quantitation of transferase activity is based on the comparison of the UV absorbance of the two conjugates at 254 nm with synthetic conjugate standards. As little as 1 nmole of either conjugate can be quantitated with good precision. This assay has advantages over previously published methods for measuring styrene oxide glutathione S-transferase activity as it does not depend on the use of relatively unstable and expensive radiolabelled substrates.

Animals↗
PubMed1995

Major groove (R)-alpha-(N6-adenyl)styrene oxide adducts in an oligodeoxynucleotide containing the human N-ras codon 61 sequence: conformations of the R(61,2) and R(61,3) sequence isomers from 1H NMR.

Conformations of (R)-alpha-(N6-adenyl)styrene oxide adducts at positions X6 in d(CGGACXAGAAG).d(CTTCTTGTCCG) and X7 in d(CGGACAXGAAG).d(CTTCTTGTCCG), incorporating codons 60, 61 (underlined), and 62 of the human n-ras protooncogene, were refined from 1H NMR data. These were the R(61,2) and R(61,3) adducts. Chemical shift perturbations were in the 5'-direction from the sites of adduction; large changes were observed for C5 H5 and H6 in the R(61,2) adduct. The styrene moieties were only partially defined by NOE data. Spectral overlap, particularly for the R(61,2) adduct, prevented complete assignments of the aromatic resonances; likewise, there were insufficient data to orient the CH2OH moieties. Ring flips were slow on the NMR time scale. For the R(61,2) adduct 260 restraints were obtained from NOE data at three mixing times using relaxation matrix analysis; for the R(61,3) adduct 230 restraints were obtained. Structures emergent from molecular dynamics/simulated annealing for the R(61,2) adduct converged to average and maximum pairwise rms differences of 1.3 and 1.7 A, respectively, while those for the R(61,3) adduct converged to average and maximum pairwise rms differences of 1.2 and 1.6 A. Sixth root residual indices of 7.5 and 6.8 x 10(-2) were measured between the refined structures and NOE intensities using relaxation matrix calculations for the R(61,2) and R(61,3) adducts, respectively. The styrene rings were in the 5'-direction from the lesion sites in the major groove. The preferred orientation calculated for the R(61,2) adduct placed the styrene ring edgewise and approximately orthogonal to C5, while that calculated for the R(61,3) duplex had the styrene ring approximately orthogonal to the major groove edges of base pairs A6.T17 and R-SOA7.T16.

Adenine↗
PubMed2005

Protection-deprotection chemistry to control styrene self-directed line growth on hydrogen-terminated Si(100).

TEMPO, 2,2,6,6-tetramethylpiperidinyloxy, was used in a series of protection-deprotection chemical reactions in order to gain single molecule-level control over the extent of styrene line growth on hydrogen-terminated Si(100). The mechanism involves the reaction of TEMPO with the dangling bond at the end of individual styrene lines. The TEMPO cap protects the dangling bond from further reaction with styrene resulting in the termination of line growth. TEMPO is then selectively removed from desired lines, deprotecting the dangling bond, using the scanning tunneling microscope. Further exposure of the surface to styrene ensures that only the deprotected areas continue to grow while the protected lines do not. All lines can then be capped with TEMPO, and this allows for the generation of stable styrene lines of varying lengths.

Journal Article↗
PubMed2005

Selective oxidation of styrene on an oxygen-covered Au(111).

For the first time, we demonstrate olefin epoxidation promoted by an extended Au surface. The oxidation of styrene to styrene epoxide, benzoic acid, and benzeneacetic acid is promoted on Au(111) covered with 0.2 ML of oxygen atoms. The estimated selectivity for styrene epoxide formation is approximately 53%. Total combustion to CO2 accounts for approximately 20% of the styrene reaction. We propose that styrene epoxide, benzoic acid, and benzeneacetic acid are produced via two possible oxametallacycle intermediates. Our work demonstrates that extended Au is an effective material for olefin oxidation, which has implications for understanding the activity of nanoscale Au catalysts.

Journal Article↗
PubMed2003

Biocatalysis of nitro substituted styrene oxides by non-conventional yeasts.

Yeast strains (410) from more than 45 different genera were screened for the enantioselective hydrolysis of nitro substituted styrene oxides. These strains included 262 yeasts with known epoxides hydrolase activity for various other epoxides. Epoxide hydrolase activity for p-nitrostyrene oxide (pNSO) (177 strains) and m-nitrostyrene oxide (mNSO) (148 strains) was widespread in the yeasts, while activity for o-nitrostyrene oxide (oNSO) was less ubiquitous (22 strains). The strains that displayed enantioselectivity in the hydrolysis of one or more of the nitro substituted styrene oxides (35 strains) were also screened against styrene oxide (SO). Rhodosporidium toruloides UOFS Y-0471 displayed the highest enantioselectivity for pNSO (ee 55%, yield 35%) while Rhodotorula glutinis UOFS Y-0653 displayed the highest enantioselectivity for mNSO (ee > 98%, yield 29%), oNSO (ee 39%, yield 19%) and SO (ee > 98%, yield 19%). (R)-Styrene oxide was preferentially hydrolysed to the corresponding (R)-diol with retention of configuration at the stereogenic centre. In the case of the nitro substituted styrene oxides the absolute configurations of the remaining epoxides and the formed diols were not established.

Catalysis↗
PubMed1992

Identification of N2-substituted 2'-deoxyguanosine-3'-phosphate adducts detected by 32P-postlabeling of styrene-oxide-treated DNA.

Styrene-7,8-oxide, a metabolite of the industrial chemical styrene, was reacted with calf thymus DNA. Six adducts were detected by 32P-postlabeling. The two diastereomers of N2-(2-hydroxy-1-phenylethyl)-2'-deoxyguanosine-3'-phosphate and the corresponding N-1 substituted compounds were isolated from the aqueous reaction mixture of 2'-deoxyguanosine-3'-phosphate and styrene-7,8-oxide (pH 10.5) and characterized by liquid secondary-ion and four-sector tandem mass spectrometry, ultraviolet, circular dichroism, and fluorescence spectrophotometry, and 32P-postlabeling. Co-chromatography of the DNA-styrene-7,8-oxide reaction products with the synthetic standards showed that adduct no. 6 arose as a result of aralkylation at the N2-exocyclic site of the guanine base. The recovery of the N2-adduct was dependent on the concentration of the solvent used during octadecylsilyl chromatography. These studies revealed that the N2-guanosine derivatives are the major products of the reaction of DNA and styrene-7,8-oxide in vitro detected by 32P-postlabeling.

Autoradiography↗
PubMed1988

Detection of styrene oxide-DNA adducts by 32P-postlabeling.

In vitro reaction of DNA with styrene-7,8-oxide (styrene oxide) produced five adducts, as determined by 32P-postlabeling. When styrene oxide was reacted in vitro with deoxyribonucleotides, five adducts were observed from 2'-deoxyguanosine-3'-monophosphate, two from 2'-deoxyadenosine-3'-monophosphate, none from 2'-deoxythymidine-3-monophosphate or 2'-deoxycytidine-3'-monophosphate. Chromatographic comparison of the adducts formed in DNA with those formed with the deoxyribonucleotides suggests that deoxyguanosine is the primary site of DNA modification. Treatment of 9L cells with 1 mM styrene oxide resulted in the formation of several DNA adducts as detected by the postlabeling procedure. Our results indicate that 32P-postlabeling can be used to investigate DNA adducts formed by styrene oxide.

DNA↗
PubMed1983

Reproductive-toxicologic assessment of the epoxides ethylene oxide, propylene oxide, butylene oxide, and styrene oxide.

Ethylene oxide (CAS no 75-21-8), propylene oxide (CAS no 75-56-9), butylene oxide (CAS no 106-88-7), and styrene oxide (CAS no 96-09-3) were tested for teratogenic activity by inhalation exposure of rats and rabbits. Ethylene oxide and propylene oxide were tested at only one concentration in both species (150 ppm for ethylene oxide and 500 ppm for propylene oxide). Butylene oxide was tested at 250 and 1,000 ppm in both species, while styrene oxide was tested at 100 ppm in rats and 15 and 50 ppm in rabbits. For each of these four epoxides, the acute toxicity was similar for pregnant and nonpregnant rats. Styrene oxide was the most toxic in both species, and rabbits were more sensitive than rats. Rats exposed to propylene oxide for 7 h/d, 5 d/week for three weeks before breeding had a significant reduction in the number of corpora lutea. Fetal mortality was not increased, but significantly fewer mated rats were found pregnant following gestational exposure to styrene oxide, a finding suggesting preimplantation loss. In rabbits exposed to styrene oxide, the number of resorptions per litter was increased in concentration related manner, but differences were not statistically significant. Fetal examination revealed evidence of fetotoxicity with all four epoxides. There was no overt teratogenic activity, but a number of minor morphologic aberrations were detected.

Abnormalities, Drug-Induced↗
PubMed2000

[Asymmetric biosynthesis of chiral styrene oxide].

Used styrene as the sole carbon and energy source, 12 strains of aerobic bacterial and two strains of fungi were screened from a series soil samples. These strains were able to convert styrene to styrene oxide. HPLC and chiral GC method were used for determination the substrate, product and e.e value of culture broth. There were obvious effect on the biomass and epoxidase activity under various conditions in the fermentation. Styrene epoxidation of the strain PS-1206 was studied in different reaction time. 35% of conversion yield and 80% e.e value of (R)-styrene oxide could been obtained at the optimum conditions.

Bacteria↗
PubMed1993

DNA binding and stimulation of cell division in the carcinogenicity of styrene 7,8-oxide.

[7-3H]Styrene 7,8-oxide was administered by oral gavage to male CD rats at a dose of 1.3 mg/kg. After 4 h, the forestomach was excised, DNA was isolated, purified to constant specific radioactivity and degraded enzymatically to the 3'-nucleotides. High-performance liquid chromatography fractions with the normal nucleotides contained most of the radiolabel, but a minute level of adduct label was also detected. Using the units of the covalent binding index (micromoles adduct per mole DNA nucleotide)/(millimole chemical administered per kilogram body weight), a DNA binding potency of 1.0 was derived. A comparison of the covalent binding indices and carcinogenic potencies of other genotoxic forestomach carcinogens showed that the tumorigenic activity of styrene oxide is unlikely to be purely genotoxic. Therefore, styrene oxide was compared with 3-t-butylhydroxyanisole (BHA) with respect to stimulation of cell proliferation in the forestomach. Male Fischer 344 rats were treated for four weeks at three dose levels of styrene oxide (0, 137, 275 and 550 mg/kg, three times per week by oral gavage) and BHA (0, 0.5, 1 and 2% in the diet); the highest doses had been reported to result in 84% and 22% carcinomas in the forestomach, respectively. Cell proliferation was assessed by incorporation of bromodeoxyuridine into DNA and immunohistochemical analysis. An increase in the labelling index was found in all treated animals. In the prefundic region of the forestomach, the labelling index increased significantly, from 42% (controls) to 54% with styrene oxide and from 41 to 55% with BHA.(ABSTRACT TRUNCATED AT 250 WORDS)

Administration, Oral↗
PubMed1993

The replication fate of R- and S-styrene oxide adducts on adenine N6 is dependent on both the chirality of the lesion and the local sequence context.

In order to deduce the biological fate of adducts formed by the reaction of styrene oxide, a suspected carcinogen, with DNA, four oligodeoxynucleotides were synthesized which contained either R- or S-styrene oxide lesions on the N6 position of neighboring adenines within the human N-ras codon 61. When these adducted oligodeoxynucleotides were ligated into the single-stranded vector M13mp7L2 and the modified DNA used to transform repair-deficient Escherichia coli, the resultant plaque-forming abilities were found to vary as much as 300-fold, depending on the stereochemical configuration of the styrene oxide lesion and the sequence context in the vicinity of the damage. The frequency of mutations caused by the various styrene oxide adducts were similarly dependent on both their chirality and local sequence context. Oligodeoxynucleotide templates bearing these same four adducts were also constructed in order to evaluate their replication in vitro by the Klenow fragment. Three of the four styryl-modified templates yielded significant levels of fully extended primer upon polymerization. In contrast, the template containing R-styrene oxide at the second position of N-ras 61 was a very poor substrate for replication, a result which correlates well with the observed lethality of this lesion in vivo.

Adenine↗
PubMed1985

Styrene vapor control systems in FRP yacht plants.

The production of large (greater than 25-ft) fiber-reinforced plastic (FRP) yachts has presented problems of styrene exposure in excess of the Occupational Safety and Health Administration permissible exposure level (OSHA PEL) of 100 ppm. Also, the National Institute for Occupational Safety and Health (NIOSH) is currently recommending a 10-hour workshift, 40-hour workweek time weighted average (TWA) of 50 ppm for styrene. Meeting this challenge will require a system of engineering, work practice, personal protective equipment, and monitoring control measures. NIOSH has performed a study of the engineering controls in three FRP yacht plants. Work practices and the use of personal protective equipment (PPE) were also considered in the evaluation. The three systems evaluated included a dilution system, a local ventilation system, and a push-pull ventilation system. The cost of constructing and operating these systems was not evaluated in this study. Study results indicated that each type of ventilation system can meet the present PEL of 100 ppm styrene; however, it is not certain that these systems can meet a lower PEL of 50 ppm styrene.

Air Pollutants, Occupational↗
PubMed1990

Occupational exposures to styrene in Denmark 1955-88.

An assessment of the occupational exposure to styrene and associated chemicals in Denmark was carried out by retrieving all measurements from the archives of the Danish National Institute of Occupational Health. A total of 2,528 air samples containing styrene had been collected from 256 workplaces during the years 1955-88 and analyzed by the chemical laboratory at the Institute. The mean for all samples was 265 mg/m3. The concentration decreased from 714 mg/m3 in the early period (1955-70) to 172 mg/m3 in the late period (1981-88). Spraying and unspecified lay-up and production of boats, carriages, and stationary containers were associated with the highest concentration. A total of 34 chemicals were measured. The most frequent co-contaminant to styrene was acetone, which was measured in 2,263 samples with a mean concentration of 131 mg/m3. Dichloromethane was measured in 208 samples with a mean concentration of 51 mg/m3, xylene in 148 samples with a mean concentration of 49 mg/m3, and toluene in 116 samples with a mean concentration of 113 mg/m3. The study was undertaken to analyze historical styrene concentrations in air to aid in the selection of industrial cohorts to be included in epidemiologic studies.

Air Pollutants, Occupational↗
PubMedDate not supplied

Effect of protein malnutrition on the neurobehavioural toxicity of styrene in young rats.

Neurotoxic effects of styrene on certain biochemical and behavioural indices were studied in young rats kept deficient in protein during the weaning period. Young rats fed a low-protein diet showed a significant decrease in the level of dopamine and an increase in frontocortical [3H]serotonin binding in comparison to the group of rats fed a normal protein diet. These rats also showed a significant increase in foot shock-induced aggressive behaviour, while no changes in amphetamine-induced locomotor activity, levels of norepinephrine and serotonin and binding of [3H]spiperone to striatal membrane were observed. On exposure to styrene, rats fed a normal protein diet showed a decrease in dopamine level and an increase in foot shock-induced aggressive behaviour only, with no significant change in other parameters, in comparison to the respective controls. It was, however, interesting to note that when rats fed a low-protein diet were exposed to styrene they showed a significant decrease in the levels of norepinephrine, dopamine and serotonin and an increase in the binding of [3H]spiperone and [3H]5-HT to striatal and frontocortical membranes, respectively. A significant increase in foot shock-induced aggressive behaviour and amphetamine-induced locomotor activity was also observed in this group of animals in comparison to those fed a low-protein diet. The biochemical and behavioural data indicate that protein deficiency makes young animals more vulnerable and it is an important predisposing factor in the neurobehavioural toxicity of styrene.

Aggression↗
PubMed1993

Styrene inhalation toxicity studies in mice. I. Hepatotoxicity in B6C3F1 mice.

Studies were conducted to evaluate the toxic effects of short-term repeated styrene inhalation in B6C3F1 mice. Male and female mice were exposed to 0, 125, 250, or 500 ppm styrene, 6 hr/day, for up to 14 days. Styrene toxicity was characterized by severe centrilobular hepatic necrosis and deaths after one exposure to 500 ppm or two exposures to 250 ppm. Mortality and hepatotoxicity were not increased by additional exposures, and in surviving mice, regeneration and repair of initial hepatic injury occurred in spite of continued exposure for 14 days. A marked sex difference was observed, with male mice significantly more susceptible to styrene toxicity than females. A nonlinear dose response was observed where mortality in male and female mice was greater in the 250 ppm dose group than that in the 500 ppm dose group. Severe congestion and necrosis of the liver was present in moribund mice; hepatic congestion and serum alanine aminotransferase and sorbitol dehydrogenase were significantly greater in moribund animals.

Administration, Inhalation↗
PubMed1997

Subchronic inhalation studies of styrene in CD rats and CD-1 mice.

Groups of 10 male and 10 female Charles River (CRL) CD (Sprague-Dawley-derived) rats were exposed to styrene vapor at 0, 200, 500, 1000, or 1500 ppm 6 hr per day 5 days per week for 13 weeks. Styrene had no effect on survival, hematology, or clinical chemistry. Males at 1500 ppm weighed 10% less after 13 weeks and males and females at 1000 and 1500 ppm consumed more water than controls. Histopathologic changes were confined to the olfactory epithelium of the nasal mucosa. Groups of 20 male and 20 female CRL CD-1 and B6C3F1 mice were exposed to styrene vapor at 0, 15, 60, 250, or 500 ppm 6 hr per day 5 days per week for 2 weeks. Mortality was observed in both CD-1 and B6C3F1 mice exposed to 250 or 500 ppm; more female mice, but not males, died from exposure to 250 ppm than from 500 ppm. Groups of 10 male and 10 female CRL CD-1 mice were exposed to styrene vapors at 0, 50, 100, 150, or 200 ppm 6 hr per day 5 days per week for 13 weeks. Two females exposed to 200 ppm died during the first week. Liver toxicity was evident in the decedents and in some female survivors at 200 ppm. Changes were observed in the lungs of mice exposed to 100, 150, or 200 ppm and in the nasal passages of all treatment groups, those exposed to 50 ppm being less affected. Satellite groups of 15 male rats and 30 male mice were exposed as described above for 2, 5, or 13 weeks for measurement of cell proliferation (BrdU labeling). No increase in cell proliferation was found in liver of rats or mice or in cells of the bronchiolar or alveolar region of the lung of rats. No increase in labeling index of type II pneumocytes was seen in mouse lungs, while at 150 and 200 ppm, an increased labeling index of Clara cells was seen after 2 weeks and in occasional mice after 5 weeks. Large variations in the labeling index among animals emphasize the need for large group sizes. For nasal tract effects, a NOAEL was not found in CD-1 mice, but in CD rats, the NOAEL was 200 ppm. For other effects, the NOAEL was 500 ppm in rats and 50 ppm in mice.

Administration, Inhalation↗
PubMed1995

A model for estimating the daily dietary intake of a substance from food-contact articles: styrene from polystyrene food-contact polymers.

An approach has been developed to estimate the exposure of consumers to styrene from polystyrene food-contact articles which incorporates published literature on the diffusion of styrene through polymeric materials and industry survey data on uses of polystyrene in food-contact applications. The approach has been shown to be quite practical and has yielded an exposure estimate of 3 ppb (9 micrograms/day) styrene, on average, in the daily diet of people in the United States. This value compares reasonably well with the value of 1-4 micrograms/day for residents of the United Kingdom in 1983. The value is also four orders of magnitude less than the acceptable daily intake calculated by the Styrene Information and Research Center.

Animals↗
PubMed1985

Some behavioral effects of early styrene intoxication in experimental animals.

Male albino rats were administered styrene in groundnut oil, PO at doses of 100 mg and 200 mg/kg body weight daily for 14 consecutive days. No neurological deficit was observed in any animal during the course of the experiment. Mean % avoidance response (learning) for each treated group, from day 1 to day 4 of conditioned avoidance response training, revealed a general increase. Styrene significantly increased the % avoidance response at both doses as compared to controls, although no definite dose-response relationship was evident. No significant difference was noted in the spontaneous locomotor activity and regional brain catecholamine levels, between controls and treated rats of either dose. Serotonin levels in hippocampus, hypothalamus, and mid-brain were significantly raised at the higher dose of styrene. Therefore, elevated serotonin levels in these brain regions may account for styrene-induced learning.

Animals↗