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PubMed1978

Exposure-response relationship between styrene exposure and central nervous functions.

For the study of the relationship between styrene exposure and symptoms and signs of central nervous dysfunctions, 98 male workers occupationally exposed to styrene were given clinical, neurophysiological and psychological examinations; also a symptom survey was made. Urinary mandelic acid concentrations, measured once a week during five consecutive weeks, were used to express the exposure intensity. Different unexposed groups were used for reference. No exposure-response relationship was observed between symptoms of ill health and the urinary mandelic acid concentration, although the exposed group as a whole expressed significantly more symptoms than the reference group. The occurrence of abnormal electroencephalograms was about 10% in the group of workers with mandelic acid concentrations below 700 mg/l, but it was 30% among those whose mandelic acid concentration exceeded 700 mg/l, a level corresponding to the 8-h time-weighted average (TWA) of styrene exposure of about 30 ppm. With regard to psychological functions, the first change in visuomotor accuracy became discernible when the urinary mandelic acid concentration exceeded 800 mg/l. A more pronounced decrement appeared in both visuomotor accuracy and psychomotor performance when the mandelic acid concentration exceeded 1,200 mg/l, which corresponds to an 8-h TWA of styrene exposure of about 55 ppm.

Adolescent↗

PubMed1991

p-Hydroxybenzoylformic acid and (R)-(-)-p-hydroxymandelic acid, two antifungal compounds isolated from the liquid culture of the ectomycorrhizal fungus Pisolithus arhizus.

Two antifungal compounds isolated from the liquid culture medium of Pisolithus arhizus were identified as p-hydroxybenzoylformic acid and (R)-(-)-p-hydroxymandelic acid and given the trivial names pisolithin A and pisolithin B, respectively. The efficacy of the compounds to inhibit the germination of conidia of Truncatella hartigii was compared with that of commercially available structural analogues, and a comparable range of effectiveness for 50% germination inhibition (GI50) of conidia was recorded. The commercially available synthetic compounds (R)-mandelic acid, benzoylformic acid, and racemic p-hydroxymandelic acid, had GI50 values of 82, 72, and 59 micrograms/mL, respectively, as compared with the natural compounds pisolithin A, 67 micrograms/mL, and pisolithin B, 71 micrograms/mL. Two synthetic S enantiomers of mandelic acid, (S)-mandelic acid and (S)-(+)-p-hydroxymandelic acid, were the most effective compounds, with GI50 values of 31 and 33 micrograms/mL, respectively. A sodium salt of mandelic acid had no activity below 500 micrograms/mL. Pisolithin A and pisolithin B were compared with polyoxin D for inhibition of hyphal growth, as measured by protein estimation. Both pisolithin A and B measured higher levels of putative extractable protein than polyoxin D, but less mycelial wet weight was measured. It is suggested that the pisolithins caused a disruption of cell turgor. A measurement of mycelial dry weights of phytopathogens, incubated with the commercially available analogues, benzoylformic acid and racemic p-hydroxymandelic acid, indicated that benzoylformic acid was either more effective than, or as effective as, racemic p-hydroxymandelic acid or nystatin in arresting fungal growth.(ABSTRACT TRUNCATED AT 250 WORDS)

Antifungal Agents↗

PubMed2002

Validated method for quantitation of biomarkers for benzene and its alkylated analogues in urine.

A validated gas chromatography-mass spectrometric method for the analysis of the metabolites of benzene and its alkylated analogues in urine is reported. A number of metabolites, as required by authorities for biomonitoring of industrial exposure to aromatic vapour, were analysed simultaneously with preservation of quantitative information concerning positional isomers. The use of this method replaces a combination of analytical methods required for the analysis of all these metabolites. Urine samples were subjected to acidic deconjugation followed by a derivatization step. Phenol, ortho-, meta-, para-cresol, mandelic acid, and ortho-, meta-, para-methylhippuric acid were analysed as their corresponding ethoxycarbonyl derivatives, with single ion monitoring. The mass-to-charge ratios (m/z) of the ions used for quantitation by single ion monitoring of the metabolites were: phenol, 94 m/z; cresols, 108 m/z; mandelic acid, 206 m/z; hippuric acid, 105 m/z; methylhippuric acids, 119 m/z. The mass-to-charge ratios for the internal standards were: [(2)H(6)]phenol, 99 m/z; p-chlorophenol, 128 m/z and 3-chloro-4-hydroxyphenyl acetic acid, 214 m/z. The limits of detection for phenol and the cresols were below 0.4 micromol/l and below 0.05 micromol/l for mandelic acid and the hippuric acids. Within-run precision for mandelic acid was 6.2%, for hippuric acid was 7.32% and was below 5% for the rest of the analytes.

Alkylation↗

PubMed2001

Effects of low-level occupational exposure to styrene on color vision: dose relation with a urinary metabolite.

To investigate the threshold effects of chronic low-level occupational exposure to styrene on color vision, we examined color discrimination in 105 male workers exposed to styrene (mean age 37.7 years; mean length of exposure 6.2 years; mean urinary concentration of mandelic acid 0.21 g/L) and in 117 referents (mean age 37.7 years). We also assessed the effects of styrene by examination of the nature of the relation between disorders of nervous function and age, alcohol consumption, and other variables. A standardized questionnaire was adopted to collect information about work history, occupational or nonoccupational solvent exposure, alcohol consumption, and drug use. Color vision was evaluated by the Lanthony desaturated panel D-15 test. The results of the test were expressed as the color confusion index (CCI). There was a dose-dependent relationship between the urinary concentration of mandelic acid and color vision loss. The CCIs of the subgroups whose urinary mandelic acid levels were 0.1-0.2 and >0.2 g/L were significantly higher than those of each referent group (P<0.05 and P<0.01, respectively), but not in the subgroup whose urinary mandelic acid level was lower than 0.1 g/L. Our study suggests that a low level of styrene, presumably 0.1-0.2 g/L, involves the risk of inducing adverse effects on color vision. After confounding factors were adjusted for, the urinary mandelic acid level had a significant positive relationship with color vision.

Adult↗

PubMed2003

A glycopeptide antibiotic chiral stationary phase for the enantiomer resolution of hydroxy acid derivatives by capillary electrochromatography.

Separation of hydroxy acid enantiomers was achieved by using capillary electrochromatography (CEC) employing a chiral stationary phase (CSP) based on MDL 63,246 (Hepta-Tyr), a macrocyclic antibiotic of the teicoplanin family. The chiral selector was chemically bonded to 5 num diol-modified silica particles and the CSP mixed with amino silica (3:1 w/w) was packed into a 75 num ID fused-silica capillary. The CEC experiments were carried out by using an aqueous reversed-phase mode for the enantiomeric resolution of hydroxy acid compounds. Good enantioresolution was achieved for mandelic acid (MA), m-hydroxymandelic acid (m-OH-MA), p-OH-MA, and 3-hydroxy-4-methoxymandelic acid (3-OH-4-MeO-MA). The CEC system was less enantioselective towards 2-phenyllactic acid (2-PhL) and 3-PhL while mandelic acid methyl ester (MA-Et-Est) enantiomers were not resolved. Several experimental parameters, such as organic solvent type and concentration, buffer pH, capillary temperature, on enantioresolution factor, retention time, and retention factor were studied.

Acetonitriles↗

PubMed1993

Enantioselective lipase-catalyzed ester hydrolysis: effects on rates and enantioselectivity from a variation of the ester structure.

In order to make a preliminary study of substituent effects on the rate and enantioselectivity obtained in esterolytic reactions catalyzed by a lipase from Candida rugosa, a series of racemic esters, derived from some alpha-alkyl and alpha-halo phenylacetic acids, were prepared. The reactions were studied at pH 6.0 and 50 degrees C under which conditions uncatalyzed hydrolysis was relatively slow. Reaction samples were studied at different points of time by means of analytical chiral reversed-phase liquid chromatography, which permitted the simultaneous determination of product enantiomeric excess and of the degree of total ester hydrolysis. These data were then used to calculate initial rates as well as enantioselectivity. An increase of the steric bulk of the alpha-substituent was found to highly decrease the rate of the reaction. On the other hand, rates were higher for the p-nitrophenyl esters than for the corresponding 2-chloroethyl esters. Consistently, the enantioselectivity was found to be higher for the latter type of ester. The esters of the alpha-halo (bromo and chloro) phenylacetic acids gave mandelic acid as the final product. This was caused by a rapid solvolysis of the alpha-halo phenylacetic acid initially formed.

Candida↗

PubMed1994

Monoamine oxidase and catecholamine metabolism.

The enzyme which has come to be known as monoamine oxidase was discovered in liver over 60 years ago as tyramine oxidase (Hare, 1928). Almost 10 years later, Blaschko et al. (1957a,b) established that epinephrine, norepinephrine and dopamine were also substrates for this enzyme. Zeller (1938) distinguished monoamine oxidase as different from several other amine oxidases, such as diamine oxidase. Although it was generally assumed that catecholamines were metabolized by MAO, this was not established until isotopically labelled epinephrine and an MAO inhibitor became available. Schayer (1951) found that after administration of N-methyl-14C-epinephrine, only about 50% of the radioactivity appeared in the urine, whereas when the 14C label was incorporated into the beta-position on the side chain, almost all of the radioactivity could be recovered. One year later, Zeller et al. (1952) discovered that isonicotinic acid hydrazide (iproniazid) inhibited MAO. When animals pretreated with the MAO inhibitor were administered N-methyl-14C-epinephrine, almost all of the radioactivity was recovered (Schayer et al., 1955), indicating that the enzyme was responsible for the metabolism of about half of the administered catecholamine. Schayer et al. (1952, 1953) had found that five urinary metabolite products of beta-labelled-14C-norepinephrine could be separated by paper chromatography, but the chemical structures of these compounds were not known. Armstrong et al. (1957) showed that 3-methoxy-4-hydroxymandelic acid (vanillyl mandelic acid, VMA) was the major metabolite of norepinephrine and Shaw et al. (1957) demonstrated that large amounts of homovanillic acid (HVA) were excreted in urine after administration of 3,4-dihydroxy-phenylalanine (DOPA). These observations led Axelrod to examine the possibility that O-methylation might precede deamination and to his discovery of catechol-O-methyl transferase (Axelrod, 1957, 1959). At that time it became apparent that there were two possible routes for metabolism of norepinephrine to VMA--either deamination followed by O-methylation or O-methylation and subsequent deamination. The relative roles of these two pathways in terminating the physiological actions of catecholamines then became a focus of attention. Biochemical methods were used to access directly the relative importance of the two metabolic pathways. Physiological methods, based on the effects of drugs which alter metabolism of the catecholamine, were used to examine the role of MAO and COMT in terminating the actions of administered or endogenously released catecholamines.

Animals↗

PubMed1993

Quality assurance of biological monitoring in view of risk management.

Since recommended occupational exposure limits both for workplace air concentration and biological monitoring results generally have very narrow margin of protection, the probability of the false decision due to measurement error should be perceived and carefully controlled. Japan Federation of Occupational Health Organization has conducted large scale quality control programs since 1987 and reported the results in detail. The meta-analysis of the report of 1992 made it clear that the qualities of the analysis of the leading laboratories as expressed by the coefficient of variation of measurement error are mostly about 5% or less. It was suggested that the warning level should be set at (biological exposure limits minus 2 SD of the measurement error). However, it will not be needed when the SD is less than 2.5% as was found for the analyses of blood lead, urinary hippuric acid, methyl hippuric acid, and mandelic acid by a few best performing laboratories.

Environmental Monitoring↗

PubMed1998

Biochemistry and biotechnology of mesophilic and thermophilic nitrile metabolizing enzymes.

Mesophilic nitrile-degrading enzymes are widely dispersed in the Bacteria and lower orders of the eukaryotic kingdom. Two distinct enzyme systems, a nitrilase catalyzing the direct conversion of nitriles to carboxylic acids and separate but cotranscribed nitrile hydratase and amidase activities, are now well known. Nitrile hydratases are metalloenzymes, incorporating FeIII or CoII ions in thiolate ligand networks where they function as Lewis acids. In comparison, nitrilases are thiol-enzymes and the two enzyme groups have little or no apparent sequence or structural homology. The hydratases typically exist as alpha beta dimers or tetramers in which the alpha- and beta-subunits are similar in size but otherwise unrelated. Nitrilases however, are usually found as homomultimers with as many as 16 subunits. Until recently, the two nitrile-degrading enzyme classes were clearly separated by functional differences, the nitrile hydratases being aliphatic substrate specific and lacking stereoselectivity, whereas the nitrilases are enantioselective and aromatic substrate specific. The recent discovery of novel enzymes in both classes (including thermophilic representatives) has blurred these functional distinctions. Purified mesophilic nitrile-degrading enzymes are typically thermolabile in buffered solution, rarely withstanding exposure to temperatures above 50 degrees C without rapid inactivation. However, operational thermostability is often increased by addition of aliphatic acids or by use of immobilized whole cells. Low molecular stability has frequently been cited as a reason for the limited industrial application of "nitrilases"; such statements notwithstanding, these enzymes have been successfully applied for more than a decade to the kiloton production of acrylamide and more recently to the smaller-scale production of nicotinic acid, R-(-)-mandelic acid and S-(+)-ibuprofen. There is also a rapidly growing catalog of other potentially useful conversions of complex nitriles in which the regioselectivity of the enzyme coupled with the ability to achieve high conversion efficiencies without detriment to other sensitive functionalities is a distinct process advantage.

Acrylamide↗

PubMed2005

Bupivacaine salts of diflunisal and other aromatic hydroxycarboxylic acids: aqueous solubility and release characteristics from solutions and suspensions using a rotating dialysis cell model.

In the search for poorly soluble bupivacaine salts potentially enabling prolonged postoperative pain relief after local joint administration in the form of suspensions the solubility of bupivacaine salts of diflunisal and other aromatic hydroxycarboxylic acids were investigated together with the release characteristics of selected 1:1 salts from solutions and suspensions using a rotating dialysis cell model. The poorest soluble bupivacaine salts were obtained from the aromatic ortho-hydroxycarboxylic acids diflunisal, 5-iodosalicylic acid, and salicylic acid (aqueous solubilities: 0.6-1.9 mM at 37 degrees C). Diffusant appearance rates in the acceptor phase upon instillation of solutions of various salts in the donor cell applied to first-order kinetics. Calculated permeability coefficients for bupivacaine and the counterions diflunisal, 5-iodosalicylic acid, and mandelic acid were found to be correlated with the molecular size of the diffusants. Release experiments at physiological pH involving suspensions of the bupivacaine-diflunisal salt revealed that at each sampling point the diflunisal concentration exceeded that of bupivacaine in the acceptor phase. However, after an initial lag period, a steady state situation was attained resulting in equal and constant fluxes of the two diffusants controlled by the permeability coefficients in combination with the solubility product of the salt. Due to the fact that the saturation solubility of the bupivacaine-salicylic acid salt in water exceeded that of bupivacaine at pH 7.4, suspensions of the latter salt were unable to provide simultaneous release of the cationic and anionic species at pH 7.4. The release profiles were characterised by a rapid release of salicylate accompanied by a much slower appearance of bupivacaine in the acceptor phase caused by precipitation of bupivacaine base from the solution upon dissolution of the salt in the donor cell.

Bupivacaine↗

PubMed2002

Asymmetric intramolecular [2 + 2] photocycloadditions: alpha- and beta-hydroxy acids as chiral tether groups.

Chiral alpha- and beta-hydroxy acids such as (S)-lactic acid, (S)-phenyllactic acid, (S)-mandelic acid, or (3R)-3-hydroxybutyric acid have been used as tether groups for intramolecular and diastereoselective [2 + 2] photocycloaddition of 3-oxocyclohexene carboxylic acid derivatives. Total regiocontrol toward the straight adduct and high diastereoselectivities (up to 94%) were observed in the case of butenyl lactate 11. After separation of the two diastereoisomers, cleavage of the chiral tether under basic conditions afforded cyclobutane lactones in good yield and enantiomeric pure form. An X-ray structure has been recorded that confirmed the relative and absolute configuration of the three contiguous stereogenic centers assigned according to CD spectra.

Journal Article↗

PubMed2003

Effects of clay minerals on Cr(VI) reduction by organic compounds.

The objective of this study is to examine the effect of clay minerals (illite, montmorillonite, and kaolinite) on chromate (Cr(VI)) reduction by several low molecular weight organic compounds. Batch experiments at pH ranging from 3.0 to 6.0 and 25 degrees C showed that 2:1 layered clays illite and smectite catalyzed Cr(VI) reduction by oxalate. The catalytic effect increased as pH was decreased. The 1:1 clay kaolinite had no catalytic effect under comparable conditions. Direct Cr(VI) reduction by reactive moieties associated with illite and montmorillonite was observed, but at a much slower rate than the catalytic pathway. Cr(VI) reduction by glyoxylic acid, glycolic acid, lactic acid, and mandelic acid was accelerated by illite, although aqueous phase reduction might occur in parallel. These results suggest that Cr(VI) reduction rates in subsurface environments rich in organic compounds may be elevated through catalysis of surface-bound metals and/or soluble species from the clay minerals, and as a result, higher than those expected from aqueous phase reaction alone. Such rate enhancement for Cr(VI) reduction needs to be accounted for when developing new remedial techniques for chromium site remediation or assessing its natural attenuation.

Aluminum Silicates↗

PubMed2001

Toxicity and biodegradation of products from polyester hydrolysis.

Toxicity of products from polyester hydrolysis such as succinic acid (SA), adipic acid (AA), mandelic acid (MA), terephthalic acid (TA), 1,4-butanediol (1,4-B), ethylene glycol (EG), styrene glycol (SG) and 1,4-cyclohexane dimethanol (1,4-C) was evaluated by phytotoxicity test on germination of young radish seeds and by cytotoxicity test on HeLa cells. The phytotoxicity test revealed SG > MA > 1,4-C > AA approximately SA > TA approximately EG > 1,4-B in order of decreasing toxicity taking into consideration the growth behavior after germination as well as the percentage of germination. Toxicity on HeLa cells decreased in slightly different order compared to that on young radish seeds, i.e. SG > 1,4-C > MA > TA > SA > AA > EG > 1,4-B. Tests for the phytotoxicity and for cytotoxicity indicated that the aromatic compounds were more harmful than the aliphatic ones. Each group of 4 strains which grew most rapidly on each agar plate containing SA, AA, MA, TA, 1,4-B, EG, SG and 1,4-C respectively as a sole carbon source was identified by the fatty acid methyl esters analysis. The modified Sturm test was carried out using the single isolated strain, an activated sludge or a mixed soil to measure the rate of mineralization of the compounds into carbon dioxide. The aliphatic compounds were mineralized more easily than the aromatic compounds. 1,4-C showed the most exceptionally slow degradation. A scrutiny of residual 1,4-C after degradation is required before polyesters containing 1,4-C could be classified into compostable because 1,4-C has detrimental effects on young radish seeds and HeLa cells and has a tendency to accumulate in the environment due to its slow degradability.

Animals↗

PubMed1991

Activity of some antiseptics against urinary tract pathogens growing as biofilms on silicone surfaces.

The activity of chlorhexidine, mandelic acid and a mandelic/lactic mixture were tested against biofilms of four species of gram-negative nosocomial organisms that commonly infect the catheterized urinary tract. Cells growing on silicone discs were exposed to concentrations of agents used in bladder instillation. Citrobacter diversus biofilms proved to be sensitive to all three agents. Pseudomonas aeruginosa, Proteus mirabilis and Klebsiella pneumoniae all survived well in chlorhexidine but their viability was significantly reduced by the mandelic acid formulations. These results suggest that bladder instillations of mandelic acid or mandelic/lactic acids would be more effective than chlorhexidine in eliminating biofilms from catheter surfaces.

Anti-Infective Agents, Urinary↗

PubMed2005

Influence of steric hindrance on enantioseparation of Dns-amino acids and pesticides on terguride based chiral selectors in capillary electrophoresis.

Three urea derivatives of ergoline-based chiral selectors (CSs), differing in the size of the urea side chain, i.e. dimethyl- (CSI), diethyl- (CSII), and diisopropylurea (CSIII), were used to study the effect of steric hindrance on the enantioseparation of dansyl amino acids (Dns-AAs), pesticides, and mandelic acid under condition of capillary electrophoresis (CE) in linear polyacrylamide coated capillaries. A mixture of organic modifiers (MeOH/THF, 4:1 v/v) in a BGE consisting of 100 mM beta-alanine-acetate was used to increase the solubility of CSs up to 25 mM. The capillary was filled with CS (high UV absorption), and the inlet and outlet vials contained buffer solutions only. The best enantioseparation of Dns-AAs was achieved on CSI. Increased steric hindrance of the chiral binding site led to reduction of both enantioselectivity and resolution. The opposite pattern was observed for the separation of mandelic acid enantiomers, where the best enantioseparation and resolution was obtained with CSIII. Most of the pesticides studied reached maximum selectivity on the diethylurea ergoline derivative (CSII). Enantioseparation of fenoxaprop was found to be independent of steric hindrance.

Amino Acids↗

PubMed1991

Activity of antiseptics against biofilms of mixed bacterial species growing on silicone surfaces.

As part of a programme to establish the relative merits of antiseptics that are used as bladder instillations to control urinary tract infections in patients with indwelling catheters, the activity of five such formulations were tested against dense (10(9) cfu/cm2) mixed biofilms composed of Citrobacter diversus, Pseudomonas aeruginosa and Enterococcus faecalis growing on silicone discs. All three species were resistant to chlorhexidine (200 mg/l) and povidone-iodine (1% v/v) in the biofilm mode of growth, whereas these agents rapidly eliminated viable cells from urine suspensions of the mixed community. Lactic acid (1% v/v) produced a 1 log reduction of the biofilm population within 30 min of exposure. The mandelic acid (1% w/v) and mandelic acid (0.5% w/v)/lactic acid (0.5% v/v) mixture proved to be the most effective in eliminating the biofilm organisms. It is suggested that these latter solutions should now be tested for efficacy in bladder washouts against urinary tract infections in catheterized patients.

Anti-Infective Agents, Urinary↗

PubMed1991

Activity of antiseptics against biofilms of mixed bacterial species growing on silicone surfaces.

Anti-Infective Agents, Local↗

PubMed1989

Activity of antiseptics against Escherichia coli growing as biofilms on silicone surfaces.

The activity of chlorhexidine, acetic, lactic and mandelic acids were examined against biofilms of Escherichia coli established on silicone discs and against the test strain growing in suspension in urine. The results showed that the concentrations of chlorhexidine and acetic acid normally used for bladder instillations to control infections in patients with indwelling catheters failed to eliminate cells from the biofilm in exposure periods of up to 2 h. Lactic acid (1% v/v) had a bactericidal effect on planktonic cells but poor activity against cells in the biofilm. Mandelic acid (1% v/v), and mandelic (1% v/v) and lactic acid (1% v/v) mixtures eliminated organisms from both suspensions and biofilms. It is suggested that these solutions be considered as alternatives to acetic acid and chlorhexidine for the washing of catheterized bladders.

Acetates↗