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PubMed1998

[The use of biological monitoring in the assessment of occupational exposure to styrene in fiberglass-reinforced plastics industry].

A field study was carried out in order to investigate the effect of occupational exposure to styrene on the urinary excretion of mandelic and phenylglyoxylic acids (MA and PGA). Over a period of three years, 210 periodical, prophylactic examinations were performed on 66 fiberglass-reinforced plastics workers. The examinations embraced environmental and biological monitoring, which involved the measurement of styrene concentration in the air and the excretion rate of urinary MA and PGA. An eight-hour time-weighed average (MAC) exposure values ranged from 16.1 to 246 mg/m3 (mean: 76.1 mg/m3). The average urinary excretion rates of MA and PGA were 17.7 (1-202) and 28.8 (2-267) mg/h, respectively. The measurements of MA excretion rate were compared with the measurements of styrene concentration in the air. It seems advisable to investigate whether the recommended biological limits value of 16 mg/h for mandelic acid is not too high in view of the binding OEL value of 50 mg/m3 for styrene.

Adult↗
PubMed2006

Enantioconvergent production of (R)-1-phenyl-1,2-ethanediol from styrene oxide by combining the Solanum tuberosum and an evolved Agrobacterium radiobacter AD1 epoxide hydrolases.

Soluble epoxide hydrolase (EH) from the potato Solanum tuberosum and an evolved EH of the bacterium Agrobacterium radiobacter AD1, EchA-I219F, were purified for the enantioconvergent hydrolysis of racemic styrene oxide into the single product (R)-1-phenyl-1,2-ethanediol, which is an important intermediate for pharmaceuticals. EchA-I219F has enhanced enantioselectivity (enantiomeric ratio of 91 based on products) for converting (R)-styrene oxide to (R)-1-phenyl-1,2-ethanediol (2.0 +/- 0.2 micromol/min/mg), and the potato EH converts (S)-styrene oxide primarily to the same enantiomer, (R)-1-phenyl-1,2-ethanediol (22 +/- 1 micromol/min/mg), with an enantiomeric ratio of 40 +/- 17 (based on substrates). By mixing these two purified enzymes, inexpensive racemic styrene oxide (5 mM) was converted at 100% yield to 98% enantiomeric excess (R)-1-phenyl-1,2-ethanediol at 4.7 +/- 0.7 micromol/min/mg. Hence, at least 99% of substrate is converted into a single stereospecific product at a rapid rate.

Agrobacterium tumefaciens↗
PubMedDate not supplied

Rat peritoneal macrophage adhesion to hydroxyethyl methacrylate-ethyl methacrylate copolymers and hydroxystyrene-styrene copolymers.

Macrophage adhesion to a wide variety of substrates has been measured, but no systematic study of the influence of specific substrate chemical properties on adhesion is available. These studies were conducted using two series of materials, copolymers of hydroxyethyl methacrylate (HEMA) and ethyl methacrylate (EMA) and copolymers of hydroxystyrene and styrene, to determine the effect of a single chemical property, polar character, on adhesion. Rat peritoneal macrophages were allowed to contact polymer substrates for periods ranging from 1 to 240 min before being subjected to a shear stress of 60-120 dynes/cm2 in a thin-channel flow cell. Percentage adhesion was calculated from the number of cells that remained adherent to the substrate after 30 s of applied shear stress. Macrophages remained adherent to 100% EMA and all hydroxystyrene-styrene copolymer surfaces after only 1 min of contact. In copolymers of the HEMA-EMA series, the time required to attain peak adhesion levels increased with increasing substrate hydrophilicity (increasing HEMA content). Cells did not attach to the 20% EMA/80% HEMA copolymer and the 100% HEMA polymer. The results demonstrate that there is a time delay between contact and adhesion of the cells to surfaces of increasing hydrophilicity within the HEMA-EMA series and no time delay with the hydroxystyrene-styrene series. The time delay is thought to be a function of the excluded volume provided by polymers that are able to undergo significant chain rotation and or swelling in the solvent, water. Small excluded volumes present in copolymers of high EMA content and all hydroxystyrene-styrene copolymers offer little or no resistance to formation of adhesive bonds by macrophages, whereas copolymers with large excluded volumes (high HEMA content) prevent contact and/or adhesion. A mechanism based on the net excluded volumes of both the cell and substrate surface macromolecule is proposed to explain this phenomenon.

Animals↗
PubMed1986

Binding of styrene oxide to amino acids, human serum proteins and hemoglobin.

The covalent binding of 3H-styrene oxide to amino acids, and whole human blood was investigated in vitro. After reaction, serum, and red cells were separated, and proteins were digested into amino acids; styrene oxide derivatives were isolated by HPLC. The order of binding to free amino acids was cysteine much greater than histidine greater than lysine greater than serine. In serum proteins and hemoglobin cysteine-derivatives predominated. When styrene oxide was reacted with free cysteine and with proteins two isomers were observed. These were likely to present binding through the alpha and beta carbon of styrene oxide, and their abundance was about 2:1.

Amino Acids↗
PubMed1981

Mutagenicities of styrene oxide derivatives on bacterial test systems: relationship between mutagenic potencies and chemical reactivity.

The reaction products of deoxyguanosine with 3,4-dimethyl-, p-methyl-, m-methyl-, m-methoxy-, p-bromo-, m-chloro- and unsubstituted styrene oxide were isolated and characterized. The reaction followed second-order kinetics. The reactive site was the N-7 site of guanine. The normal isomer (attack at CH2 of styrene oxides) and the abnormal isomer (attack at CH) were obtained. The Hammett reaction constant (rho) for the normal reaction was +0.42 and that for the abnormal reaction was -1.1. The difference of acid dissociation constant, rate of imidazole ring opening and rate of glycosidic bond cleavage was not found between the normal adduct and the abnormal adduct. Styrene oxides have been tested for toxicity and mutation in a liquid suspension assay using Escherichia coli WP2 and some of its repair deficient derivatives. Salmonella typhimurium TA100 was also employed. The mutation frequency of 3,4-dimethylstyrene oxide was higher in CM571 than in WP2. The greatest mutability was found with the WP2uvrA strain. 3,4-Dimethylstyrene oxide also acted as an inducer of E. coli K-12 (kappa). The mutagenicity of 3,4-dimethylstyrene oxide may depend on a combination of the recA-dependent and recA-independent action mechanisms. The mutagenicities of these compounds in WP2uvrA and TA100 increased in the order: m-chlorostyrene oxide = p-bromostyrene oxide less than m-methoxystyrene oxide less than styrene oxide less than m-methylstyrene oxide less than p-methylstyrene oxide less than 3,4-dimethylstyrene oxide. There was no correlation between the mutagenicities and the total reaction rates. On the other hand, the reaction rates of these compounds for the abnormal reaction correlated with their mutagenicities. The results indicate that the mutagenic effect of a chemical is not dependent simply on the quantity of the adducts, but may vary with structure of its adducts.

Bacteriophage lambda↗
PubMed1981

Synthesis and relative stereochemistry of the four mercapturic acids derived from styrene oxide and N-acetylcysteine.

The chemical reaction between (+/-)-styrene oxide and N-acetylcysteine produces both positional isomers (1 and 2) as a mixture of diastereoisomers with a preference for the benzylic thioether isomer 1 (2 : 1). Synthesis of the mercapturic acid conjugates from either (+)- or (-)-styrene oxide produces only two of the four possible stereoisomers. The single diastereoisomers of 1 and 2 were separated by high pressure liquid chromatography (HPLC) and identified by 1H- and 13C-nuclear magnetic resonance (NMR). The relative stereochemistry at the benzylic carbon center of the mercapturic acid conjugates was assigned on the basis of the established chemical correlation between optically pure styrene oxide and its precursor mandelic acid, and considerations on the mechanism of ring opening of epoxides by sulfur nucleophiles. The stereochemical definition of the isomers 3-6 should prove useful in investigations of the biotransformation of the glutathione (GSH) conjugates of styrene oxide.

Acetylcysteine↗
PubMed1983

Perinatal development of styrene monooxygenase and epoxide hydrolase in rat liver microsomes and nuclei.

Nuclear enzymes were found to develop earlier than the corresponding microsomal activities. In fact styrene monooxygenase enzymatic activity at 18 days gestational age reached about half the values of adult animals, whereas fetal microsomal activity was only about 1/20 the adult level at the same age. In microsomes and nuclei the ontogenic development of epoxide hydrolase is slightly slower than styrene monooxygenase. This suggests that fetuses and newborn animals are exposed to higher risk of accumulation of styrene-7,8-oxide, a toxic and possibly teratogenic product of styrene monooxygenase.

Age Factors↗
PubMed1984

A carcinogenicity study of styrene-7,8-oxide in rats.

Styrene-7,8-oxide (200 mg/kg body wt) was given orally to female BDIV rats on 17th day of pregnancy. Their offspring received 96 weekly doses of styrene oxide (100-150 mg/kg body wt). Following the continuous administration of styrene oxide, an increased incidence, statistically significant, of forestomach tumours was observed in rats of both sexes. The incidence of tumours occurring at other sites was similar in treated and control animals. The present results show that styrene oxide is a direct-acting carcinogen producing benign and malignant tumours of the forestomach.

Animals↗
PubMed2003

The influence of PEO/poly(vinyl phenol-co-styrene sulfonate) aqueous complex structure on flocculation.

Colloidal suspensions were flocculated with complexes formed from high molecular weight polyethylene oxide (PEO) and a cofactor. Poly(vinyl phenol-co-potassium styrene sulfate) (PKS) or poly(styrene-co-styrene sulfonate) (PS-co-SSS) copolymers were used as the cofactors for this work. The larger the PEO/cofactor complex species, the better the initial flocculation. Factors such as increasing temperature or ionic strength that gave smaller complexes also gave poorer flocculation. Cofactor performance was sensitive to the balance of hydrophobic phenolic groups and hydrophilic styrene sulfonates. If there are too few phenolic groups, the PEO/PSK complexes are large but are too weak to give shear-resistant flocs, whereas complexes formed with high phenolic content PSK are relatively small, giving poorer flocculation but more shear-resistant flocs. Both phenyl and phenol groups are effective as the hydrophobic component in the cofactor. The hydrogen-bonding potential of phenolic cofactors does not seem to offer much advantage relative to phenyl groups. A crucial step in the flocculation is the adsorption of PEO/cofactor complex onto the target colloids. Thus, flocculation is sensitive to the target colloid surface chemistry. Positively charged precipitated calcium carbonate and surfactant-free polystyrene latex are particularly easy to flocculate because adsorption is driven by electrostatic and hydrophobic interactions, respectively. By contrast, the latex coated with hydrophilic poly(N-isopropylacrylamide) (PNIPAM) does not flocculate because the PEO/cofactor complex does not bind to PNIPAM. Finally, the flocculation of highly negatively charged, dextran sulfate coated calcium carbonate seems to be stimulated by the presence of soluble calcium ions that make the complex less soluble and more likely to adsorb.

Journal Article↗
PubMed2001

Genotoxic effects of styrene-7,8-oxide in human white blood cells: comet assay in relation to the induction of sister-chromatid exchanges and micronuclei.

Styrene is used in the production of plastics, resins and rubber. The highest human exposures to styrene take place by inhalation during the production of fiberglass reinforced plastics. Styrene is metabolized mainly in the liver to styrene-7,8-oxide (SO), its principal in vivo mutagenic metabolite. In this study, human peripheral white blood cells were exposed to several SO concentrations (10-200 microM) in order to evaluate its genotoxic properties by means of comet assay, sister-chromatid exchanges (SCE) and cytokinesis-blocked micronucleus (MN) test, in addition to determine its clastogenic or aneugenic properties by combining MN with fluorescence in situ hybridization (FISH) procedures. Our results show that SO induces DNA damage, SCE and MN in human leukocytes in vitro at concentrations above 50 microM, and that there is a strong relationship between DNA damage, as measured by the comet assay, and cytogenetic damage induced by SO at the doses employed. SO shows preferentially a clastogenic activity and produces a cytostatic effect at high doses, reflected by the significant decrease of the calculated proliferation indices. A good dose-effect relationship is obtained in the three tests performed at the concentration range assayed.

Adult↗
PubMed2003

Effect of epoxide hydrolase and glutathione S-tranferase genotypes on the induction of micronuclei and DNA damage by styrene-7,8-oxide in vitro.

Styrene is one of the most important organic chemicals used worldwide. Its main metabolite, styrene-7,8-oxide (SO), is considered responsible for the genotoxic effects associated with exposure to styrene. SO is detoxified by hydrolysis catalyzed by epoxide hydrolase (EH), or, to a minor extent, by conjugation mediated by glutathione S-transferases (GSTs). The purpose of the present study was to investigate whether EH (exons 3 and 4), GSTP1 (exons 5 and 6), GSTM1 and GSTT1 polymorphisms have any influence on the genotoxicity of SO in human leukocytes. Peripheral leukocytes from 30 healthy donors were exposed to SO (50 and 200 micro M) and genotoxicity was evaluated by means of the micronucleus (MN) test and alkaline comet assay, using 1% DMSO as solvent control. When EH genotypes were classified in low, medium, and high with respect to the expected EH activity, an increase in induced comet tail length was observed with decreasing EH activity in SO-exposed cells. An increase was seen in induced MN frequency in EH low-activity donors. These findings are consistent with the detoxifying activity of this enzyme. In addition, increases in MN frequencies for GSTP1 *A/*B and *A/*C genotypes with regard to the wild-type homozygous *A/*A genotype were detected. This may be due to a low detoxifying activity as a consequence of altered SO affinity of the variant protein, but must be confirmed using homozygote variant individuals, not included in this study. No clear results were obtained for GSTM1 or GSTT1 genotypes, even when performing the analysis after grouping individuals with the same expected EH activity, probably due to the minor role that glutathione conjugation plays in styrene metabolism. The present in vitro findings using human leukocytes suggest that polymorphisms in EH, and, to a lesser extent, in GSTP1, may influence induction of cytogenetic and DNA damage by SO.

Adolescent↗
PubMed2001

Predominant 1,2-insertion of styrene in the Pd-catalyzed alternating copolymerization with carbon monoxide.

The regioselectivity of styrene insertion to an acyl-Pd bond was studied by NMR in (i) a stoichiomeric reaction and (ii) a copolymerization with CO. In the stoichiometric reaction of styrene with [(CH(3)CO)Pd(CH(3)CN)[(R,S)-BINAPHOS]].[B[3,5-(CF(3))(2)C(6)H(3)](4)], both 1,2- and 2,1-products were given. To mimic the real polymerization conditions, a polyketone-substituted complex [[CH(3)(CH(2)CHCH(3)CO)(n)]Pd[(R,S)-BINAPHOS]].[B(3,5-(CF(3))(2)C(6)H(3))(4)] (n approximately 14) was prepared. When this polymer-attached Pd species was treated with styrene, the 1,2-insertion product was the only detectable species. Thus, exclusive 1,2-insertion is demonstrated to be responsible for the styrene-CO copolymerization, in sharp contrast to the predominant 2,1-insertion with conventional nitrogen ligands. Chain-end analysis revealed that beta-hydride elimination took place from the 2,1-complex but not from the 1,2-complex. Thus, once 2,1-insertion occurs, rapid beta-hydride elimination proceeds to terminate the polymerization, as is common to the other phosphorus-ligand systems. The resulting Pd-H species re-initiates the copolymerization, as was proven by MALDI-TOF mass analysis of the product copolymers.

Journal Article↗
PubMed2001

Radical polymerization of styrene controlled by half-sandwich Mo(III)/Mo(IV) couples: all basic mechanisms are possible.

Density functional calculations of bond dissociation energies (BDEs) have been used as a guide to the choice of metal system suitable for controlling styrene polymerization by either the stable free radical polymerization (SFRP) or the atom transfer radical polymerization (ATRP) mechanism. In accord with the theoretical prediction, CpMo(eta(4)-C(4)H(6))(CH(2)SiMe(3))(2), 2, is not capable of yielding SFRP of styrene. Still in accord with theoretical prediction, CpMo(eta(4)-C(4)H(6))Cl(2), 1, CpMo(PMe(3))(2)Cl(2), 3, and CpMo(dppe)Cl(2) (dppe = 1,2-bis(diphenylphosphino)ethane), 4, yield controlled styrene polymerization by the SFRP mechanism in the presence of 2,2'-azobisisobutyronitrile (AIBN). This arises from the generation of a putative Mo(IV) alkyl species from the AIBN-generated radical addition to the Mo(III) compound. The controlled nature of the polymerizations is indicated by linear M(n) progression with the conversion in all cases and moderate polydispersity indices (PDIs). Controlled polymerization of styrene is also given by compounds 3 and 4 in combination with alkyl bromides. These complexes then operate by the ATRP mechanism, again in accord with the theoretical predictions. Controlled character is revealed by linear increase of M(n) versus conversion, low PDIs, a stop-and-go experiment, and (1)H NMR and MALDI-TOF analyses of the polymer end groups. The same controlled polymerization is given by a "reverse" ATRP experiment, starting from AIBN and CpMo(PMe(3))(2)Cl(2)Br, 5. On the other hand, when compound 1 or 2 is used in combination with an alkyl bromide (as for an ATRP experiment), the isolated polystyrene shows by M(n), (1)H NMR, and MALDI-TOF analyses that catalytic chain transfer (CCT) radical polymerization takes place in this case. Kinetics simulations underscore the conditions regulating the radical polymerization mechanism and the living character of the polymerization. The complexes herein described are ineffective at controlling the polymerization of methyl methacrylate.

Journal Article↗
PubMed2003

Attachment of styrene and phenylacetylene on Si(111)-7 x 7: the influence of substitution groups on the reaction mechanism and formation of pi-conjugated skeletons.

The interactions of styrene and phenylacetylene and their isotope substitutions with a Si(111)-7 x 7 surface have been studied as model systems to mechanistically understand the chemical binding of conjugated pi-electron systems to di-radical-like silicon dangling bonds of the adjacent adatom-rest atom pair. Vibrational studies show that styrene mainly binds to the surface through a diradical reaction involving both the external C=C and its conjugated internal C=C of the phenyl ring with an adjacent adatom-rest atom pair, forming a 5-ethylidene-1,3-cyclohexadiene-like skeleton. On the other hand, phenylacetylene was shown to be covalently attached to Si(111)-7 x 7 through the external C[triple bond]C, forming a styrene-like conjugation system. These experimental results are consistent with density functional theory calculations. The different binding mechanisms for styrene and phenylacetylene clearly demonstrate that reaction channels for multifunctional organic molecules are strongly dependent on the chemical and physical properties of the functional groups. The resulting pi-electron conjugation structures may possibly be employed as intermediates for further organic syntheses and fabrication of multilayer organic films on semiconductor surfaces.

Journal Article↗
PubMed2005

Probing competitive enantioselective approach vectors operating in the Jacobsen-Katsuki epoxidation: a kinetic study of methyl-substituted styrenes.

This paper describes a study of reactivity and enantioselectivity for a series of methyl-substituted styrenes in the Jacobsen-Katsuki (Mn(salen)-catalyzed) epoxidation reaction. Competition experiments provided kinetic data for the reactivity of the seven possible methyl-substituted styrenes (mono-, di- and trisubstituted) relative to styrene itself, ee values were measured by chiral GC, and absolute configurations were secured by chemical correlation. Of particular interest was the switch in absolute configuration at the benzylic position of the epoxides derived from (Z)- and (E)-alpha,beta-dimethylstyrene, respectively. The results could be rationalized in terms of an approach vector with the phenyl substituent proximal to the salen. As opposed to alkyl groups, a proximal phenyl group has very little effect on the rate of the reaction. Consideration of distal vs proximal approach allows prediction of absolute stereochemistry as a function of alkene substitution pattern. Trisubstituted alkenes with one phenyl group cis to the alkene hydrogen can be identified as a favored substrate class in the title reaction, with both rate and selectivity close to the classic (Z)-beta-substituted styrene substrates.

Journal Article↗
PubMed2006

Selectivity limitations in the heterogeneous epoxidation of olefins: branching reactions of the oxametallacycle intermediate in the partial oxidation of styrene.

The partial oxidation of olefins on Ag surfaces has been a long standing problem in surface science and is of great commercial interest. We present a temperature-programmed reaction spectroscopy (TPRS) and X-ray photoelectron spectroscopy (XPS) study of the partial oxidation of styrene on Ag(111). The reaction products are CO2, water, styrene oxide, benzene, and benzoic acid. XPS gives evidence for two different reaction intermediates that we assign to an oxametallacycle and to benzoate. The oxametallacycle seems to be the precursor for both the formation of styrene oxide and the formation of benzoate, and thus, in addition to leading to styrene oxide, also leads to undesired byproducts. The benzoate reacts further to form CO2, benzene, and benzoic acid.

Journal Article↗
PubMed2005

Acid-catalyzed ortho-alkylation of anilines with styrenes: an improved route to chiral anilines with bulky substituents.

[reaction: see text] Reaction of para-substituted anilines with styrene derivatives at elevated temperatures, when catalyzed by CF3SO3H, results in highly chemoselective ortho-alkylation of the aniline. When R = H, dialkylation can be achieved by varying the ratio of styrene to aniline. Several different substituted anilines and styrenes were examined, and good yields (42-87%) were obtained, except in the case where electron-withdrawing substituents are present on the styrene.

Journal Article↗
PubMed2000

Studies of the mechanisms of adduction of 2'-deoxyadenosine with styrene oxide and polycyclic aromatic hydrocarbon dihydrodiol epoxides.

The mechanism of adduction of 2'-deoxyadenosine by styrene oxide and polycyclic aromatic hydrocarbon dihydrodiol epoxides has been explored using (15)N(6)-labeled adenine nucleosides. The extent of reaction at N1 versus N(6) was evaluated by (1)H NMR of the N(6) adducts after allowing Dimroth rearrangement to occur. Products arising from attack at N1 followed by Dimroth rearrangement exhibited a small two-bond (1)H-(15)N coupling constant (N1-H2 J approximately 13 Hz); products from direct attack exhibited a much larger one-bond (1)H-(15)N coupling constant (J approximately 90 Hz). In the case of styrene oxide, all of the N(6) beta adduct arose by initial attack at N1, whereas the majority (70-80%) of the N(6) alpha adducts came from direct attack. The styrene oxide reaction was also studied with a self-complementary oligodeoxynucleotide (24-mer) containing nine (15)N(6)-labeled adenine residues. NMR examination of the N(6) alpha- and beta-styrene oxide adducts isolated after enzymatic degradation of the 24-mer gave very similar results, indicating that N1 attack can occur readily even with a duplexed oligonucleotide. With the PAH dihydrodiol epoxides, only naphthalene dihydrodiol epoxide exhibited significant initial reaction at N1 (50%). No detectable rearranged product was seen in reactions with benzo[a]pyrene dihydrodiol epoxide or non-bay or bay region benz[a]anthracene dihydrodiol epoxide; interestingly, a small amount of N1 attack (5-7%) was seen in the case of benzo[c]phenanthrene dihydrodiol epoxide. It appears that initial attack at N1 is only a significant reaction pathway for epoxides attached to a single aromatic ring.

Base Sequence↗