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At least 163 records · Page 9Linked to original sources
PubMed2004

Determination of phenol and o-cresol by GC/MS in a fatal poisoning case.

A fatality due to the ingestion of solution containing phenol and o-cresol is described. The pathological findings were typical of acute substantial poisoning. Blood, urine and stomach content were obtained during post mortem examinations. Phenol and o-cresol were identified using GC/MS. The extractions from autopsy materials were obtained as follows: by gel permeation with cyclohexane/dichloromethane from stomach content, by solid phase extraction (SPE) from urine and by deproteinization with acetonitrile from blood. The phenol and o-cresol concentrations in the samples were found, respectively, as follows: 115.0 and 5.0 microg/g in the stomach contents, 58.3 and 1.9 microg/ml in the blood, 3.3 and 20.5 microg/ml in the urine. Distributions of phenol in fatal poisonings have been reported, but, usually, colorimetry was used as the analytical method and it cannot exclude the interference of other phenolic compounds.

Adult↗
PubMed2006

Adsorption of the uremic toxin p-cresol onto hemodialysis membranes and microporous adsorbent zeolite silicalite.

Para-cresol CH3C6H4OH is a protein-bound solute which is not eliminated efficiently by hemodialysis systems. In this study, we present adsorption of p-cresol as a complementary process to hemodialysis. The kinetics and isotherms of adsorption onto cellulose-based membranes (cellulose diacetate and triacetate), synthetic membranes (polyamide, polysulfone, polyacrylonitrile and polymethylmethacrylate) and microporous zeolite silicalite (MFI), have been evaluated in static conditions. The results indicate that p-cresol has a low affinity to all membranes but polysulfone and polyamide and that the times to reach equilibrium conditions are slow. In contrast, equilibration time on silicalite is fast (2 min to eliminate 90%) while adsorption levels are high (maximum adsorption about 106 mg g(-1)). Adsorption onto microporous adsorbents could be a novel way to eliminate uremic toxins from blood.

Adsorption↗
PubMed2006

Rotamers of m-cresol cation studied by mass-analyzed threshold ionization spectroscopy.

We have applied two-color resonant two-photon mass-analyzed threshold ionization technique to record the vibrational spectra of the selected rotamers of m-cresol. The adiabatic ionization energies of cis and trans m-cresol are determined to be 66,933+/-5 and 67,084+/-5 cm(-1), respectively. Frequencies of the in-plane ring vibrations 6a, 1, and 9b are measured to be 528, 720, 1167 cm(-1) for the cis and 520, 698, and 1153 cm(-1) for the trans m-cresol cation. This indicates that different orientation of the OH group with respect to the CH(3) group slightly influences these ring vibrations.

Cations↗
PubMed2004

Treatment of phenol and cresols in upflow anaerobic sludge blanket (UASB) process: a review.

Upflow anaerobic sludge blanket (UASB) process has been successfully applied in the treatment of municipal and industrial wastewaters. Several researchers have investigated the suitability of the process for the treatment of phenols and phenolic wastewaters. The anaerobic treatment of phenols is still at an investigative stage. With increasing recognition of the UASB process, feasibility studies on the treatment of wastewater containing phenol and cresols (o-, m- and p- isomers) in UASB have been reviewed. It is reported that phenol concentration up to a range of 500-750 mg/L is generally not inhibitory to the UASB process. Phenol concentrations greater than 500 mg/L can be effectively treated with acclimatization of inocula, recirculation of the treated effluent and/or supplementing with co-substrates such as glucose, VFA and dilute molasses. The degradability of phenol is more than p-cresol, which in turn is more than m- and o-cresol.

Anaerobiosis↗
PubMed1990

Determination of phenol, m-, o- and p-cresol, p-aminophenol and p-nitrophenol in urine by high-performance liquid chromatography.

A method for the biological monitoring of human exposure to aromatic hydrocarbons, nitrocompounds, amines and phenols has been developed. Phenol, cresols, p-aminophenol, p-nitrophenol and their glucorono- or sulpho-conjugates, were quantified by HPLC; 4-chlorphenol was added as internal standard. After enzymatic hydrolysis, the free compounds were extracted with an organic solvent and analyzed by an isocratic HPLC Perkin Elmer system at ambient temperature and at a flow-rate of 1 ml/min. The column was a reversed-phase Pecosphere 3 x 3 C18 Perkin Elmer; the mobile phase was a 30:70:0.1 (v/v/v) methanol-water-orthophosphoric acid mixture and the chromatogram was monitored at 215 nm. Identification was based on retention time and quantification was performed by automatic peak height determination, corrected for the internal standard. The recovery was ca. 95% for phenol and cresols; 90% for p-nitrophenol; 85% for p-aminophenol; the coefficients of variance were less than 6% within analysis (n = 20) and less than 10% between analysis (n = 20). The detection limits, at a signal/noise ratio of 2, were 0.5 mg/l for phenol and cresols and 1 mg/l for p-aminophenol and p-nitrophenol.

Aminophenols↗
PubMed1998

Marked increases of aminotransferase levels after cresol ingestion.

A 26-year-old woman developed marked increases in levels of aminotransferases about 24 hours after ingestion of 70 mL of 50% cresol. Responding to supportive measures, the patient recovered without any significant complications. Cresol and/or its metabolite may have caused transient hepato-cellular injury in this patient. In cresol poisoning, hepato-cellular injury can manifest even after a 24-hour asymptomatic period.

Adult↗
PubMed2003

Formation of p-cresol:piperazine complex in solution monitored by spin-lattice relaxation times and pulsed field gradient NMR diffusion measurements.

A study of the nature of the anthelmintic p-cresol:piperazine complex in chloroform solution has been conducted using different NMR techniques: self-diffusion coefficients using DOSY; NOE, NULL, and double-selective T1 measurements to determine inter-molecular distances; and selective and non-selective T1 measurements to determine correlation times. The experimental results in solution and CP-MAS were compared to literature X-ray diffraction data using molecular modeling. It was shown that the p-cresol:piperazine complex exists in solution in a very similar manner as it does in the solid state, with one p-cresol molecule hydrogen bonded through the hydroxyl hydrogen to each nitrogen atom of piperazine. The close correspondence between the X-ray diffraction data and the inter-proton distances obtained by NULL and double selective excitation techniques indicate that those methodologies can be used to determine inter-molecular distances in solution.

Binding Sites↗
PubMed2001

Tyrosine Raman signatures of the filamentous virus Ff are diagnostic of non-hydrogen-bonded phenoxyls: demonstration by Raman and infrared spectroscopy of p-cresol vapor.

p-Cresol is a simple molecular model for the para phenolic side chain of tyrosine. Previously, Siamwiza and co-workers [(1975) Biochemistry 14, 4870-4876] investigated p-cresol solutions to identify Raman spectroscopic signatures for different hydrogen-bonding states of the tyrosine phenoxyl group in proteins. They found that the phenolic moiety exhibits an intense Raman doublet in the spectral interval 820-860 cm(-1) and that the doublet intensity ratio (I2/I1, where I2 and I1 are Raman peak intensities of the higher- and lower-wavenumber members of the doublet) is diagnostic of specific donor and acceptor roles of the phenoxyl OH group. The range of the doublet intensity ratio in proteins (0.30 < I2/I1 < 2.5) was shown to be governed by Fermi coupling between the phenolic ring-stretching fundamental nu1 and the first overtone of the phenolic ring-deformation mode nu(16a), such that when the tyrosine phenoxyl proton is a strong hydrogen-bond donor, I2/I1 = 0.30, and when the tyrosine phenoxyl oxygen is a strong hydrogen-bond acceptor, I2/I1 = 2.5. Here, we interpret the Raman and infrared spectra of p-cresol vapor and extend the previous correlation to the non-hydrogen-bonded state of the tyrosine phenoxyl group. In the absence of hydrogen bonding, the Raman intensity of the higher-wavenumber component of the canonical Fermi doublet is greatly enhanced such that I2/I1 = 6.7. Thus, for the non-hydrogen-bonded phenoxyl, the lower-wavenumber member of the Fermi doublet loses most of its Raman intensity. This finding provides a basis for understanding the anomalous Raman singlet signature (approximately 854 cm(-1)) observed for tyrosine in coat protein subunits of filamentous viruses Ff and Pf1 [Overman, S. A., et al. (1994) Biochemistry 33, 1037-1042; Wen, Z. Q., et al. (1999) Biochemistry 38, 3148-3156]. The implications of the present results for Raman analysis of tyrosine hydrogen-bonding states in other proteins are considered.

Capsid↗
PubMed1981

8 alpha-(O-Tyrosyl)flavin adenine dinucleotide, the prosthetic group of bacterial p-cresol methylhydroxylase.

8 alpha-(O-Tyrosyl)riboflavin has been synthesized by condensation of the copper complex of L-tyrosine with 8 alpha-bromotetraacetylriboflavin. The structure of this synthetic product was proven by absorption and 1H NMR spectroscopy and by chemical degradation, which yielded 1 mol of tyrosine per mol of flavin. The synthetic compound comigrated wtih the (aminoacyl)riboflavin isolated from the p-cresol methylhydroxylase of Pseudomonas putida, and both showed identical absorption and fluorescence spectral properties. 8 alpha-(O-Tyrosyl)riboflavin as well as the flavin-containing decapeptide from p-cresol methylhydroxylase undergoes reductive cleavage to form riboflavin and FAD, respectively, on anaerobic treatment with dithionite. In contrast, the native enzyme, on reduction with dithionite, yields a reduced flavin via a red (anionic) flavosemiquinone intermediate, which remains covalently bound to the protein even under denaturing conditions. 8 alpha-(O-Tyrosyl)riboflavin bound to apoflavodoxin is also not cleaved on reduction with dithionite, but, instead, a blue (neutral) semiquinone of tyrosylriboflavin is generated, which is resistant to further reduction with dithionite. Three p-cresol methylhydroxylases, isolated from different strains of Pseudomonas putida, differing in molecular weight and Km values for substrates, contain the same peptide at the flavin site. These data provide definitive proof for the existence of 8 alpha-(O-tyrosyl)riboflavin in nature.

Cresols↗
PubMed2002

Increased sensitivity to 4-chloro-m-cresol and caffeine in primary myotubes from malignant hyperthermia susceptible individuals carrying the ryanodine receptor 1 Thr2206Met (C6617T) mutation.

Malignant hyperthermia (MH) is an autosomal-dominant disorder of skeletal muscle, triggered by volatile anaesthetics and depolarizing muscle relaxants. The causative defect lies in the control of Ca(2+) release from the sarcoplasmic reticulum in skeletal muscle. Numerous mutations have been detected in the ryanodine receptor 1 (RyR1) gene, but so far an MH-causative role has only been confirmed for 16 human RyR1 mutations. In this report we show that myotubes derived from individuals carrying the RyR1 Thr2206Met (C6617T) mutation have an abnormal response of the intracellular calcium concentration to 4-chloro-m-cresol and to caffeine. Satellite cells were obtained from muscle biopsies of patients referred for diagnosing MH. The intracellular calcium concentration in response to 4-chloro-m-cresol and to caffeine was investigated by fluorescence calcium imaging. In myotubes the half-maximal activation concentration (EC(50)) for 4-chloro-m-cresol was reduced from 203 micro m (wild type) to 98 micro m (Thr2206Met), and for caffeine from 3.8 mm to 1.8 mm. From the reduction of EC(50) we conclude that the RyR1 Thr2206Met mutation is pathogenic for MH.

Amino Acid Substitution↗
PubMed1993

The effect of the inactive mutation on longevity, sex, rhythm and resistance to p-cresol in Drosophila melanogaster.

Flies carrying the inactive (iav) mutation exhibit low locomotor activity and poor mating success, both of which are associated with a deficiency in the putative neurotransmitter, octopamine. Several other aspects of the iav mutant phenotype are described here. Male and female iav mutants show a small reduction in longevity but it is not clear whether this is a consequence of the iav mutation or their inactive phenotype. Young iav males show extended attractiveness to older courting males, which supports the notion that the iav gene has a role in post-eclosional maturation. The eclosion rhythm of iav mutants is normal, discounting the possibility of a role for octopamine in the maintenance of circadian rhythm. Flies carrying the iav mutation are highly susceptible to the octopamine analogue p-Cresol. Other phenotypically inactive flies show wild type levels of p-Cresol resistance. This is attributed to the deficiency of octopamine in iav mutants because low octopamine levels may be unable to out-compete the toxic effect of p-Cresol. Some inferences on the possible mode of action of the iav gene product are discussed.

Animals↗
PubMed1977

The purification and properties of p-cresol-(acceptor) oxidoreductase (hydroxylating), a flavocytochrome from Pseudomonas putida.

The enzyme that catalyses the hydroxylation of the methyl group of p-cresol was purified from Pseudomonas putida. It has mol.wt. 115000 and appears to contain two subunits of equal molecular weight. One subunit is a c-type cytochrome and the other is a flavoprotein. Reduction of the cytochrome occurred on addition of substrate. The same enzyme catalyses both p-cresol hydroxylation and the further oxidation of the product, 4-hydroxybenzyl alcohol. The stoicheiometry of acceptor reduced per molecule of substrate oxidized is that for two dehydrogenation reactions. The Km for p-cresol is 7.3 x 10(-6) M and that for 4-hydroxybenzyl alcohol is 47.6 x 10(-6) M. The enzyme, which is assayed with phenazine methosulphate as electron acceptor, was stimulated by particulate material, which probably contains the acceptor in vivo.

Cresols↗
PubMed1985

p-Cresol methylhydroxylase. Assay and general properties.

p-Cresol methylhydroxylase from Pseudomonas putida, an anaerobic dehydrogenase that catalyses the oxidation of p-cresol to p-hydroxybenzyl alcohol and then to p-hydroxybenzaldehyde, is an enzyme of great interest in several respects. One of these is the fact that its flavoprotein and cytochrome c subunits may be reversibly dissociated with ease, with full regeneration of the activity and its native properties on recombining the components. Bisubstrate kinetic analysis of the unresolved enzyme gives parallel-line kinetics in double-reciprocal plots, whereas the reaction of the separated flavoprotein subunit with substrates is described by converging lines. The mechanistic implications of these behaviours are discussed. Reductive titration with dithionite results in the uptake of 3 electrons by the enzyme, with the intermediate formation of the anionic flavin radical [McIntire, Edmondson, Hopper & Singer (1981) Biochemistry 20, 3068-3075]. Reductive titration with substrates resulted initially only in reduction of the cytochrome subunit, followed by formation of the anionic radical and finally the fully reduced enzyme. These observations suggest rapid intermolecular electron transfer between p-cresol methylhydroxylase molecules. This paper also examines the effect of pH and ionic strength on the activity and specificity of the enzyme with respect to substrates and natural, as well as artificial, electron acceptors. The absorption coefficients of the enzyme and of its subunits in various oxidation states are also presented.

Benzyl Alcohols↗
PubMed2002

Calcium homeostasis and glucose uptake of murine myotubes exposed to insulin, caffeine and 4-chloro-m-cresol.

The modulation of glucose uptake by cytosolic calcium and the role of insulin on calcium homeostasis in insulin-target cells are incompletely understood and results are contradictory. To address this issue, we used the C2C12 murine skeletal muscle cell line model and examined the influence of caffeine and 4-chloro-m-cresol, two ryanodine receptor agonists known to mobilize intracellular calcium stores and increase cytosolic free calcium concentration. We followed 45calcium efflux, a validated indicator of cytosolic calcium concentration, and 3-O-methyl-[1-3H]-d-glucose uptake in parallel. We also determined if insulin incubation affected 45calcium influx rate. A 30-min treatment by 1 microm insulin highly significantly increased 45calcium efflux by 8.5% (P = 0.0014), despite a significant reduction of 45Ca2+ influx already measurable after 20 and 30 min of insulin stimulation (-16.6%, P = 0.0119 and -21.3%, P = 0.0047, respectively). Caffeine (1-20 mm) and 4-chloro-m-cresol (0.05-10 mm) concentration-dependently increased 45calcium efflux, the latter being more potent and efficacious. These agents, in a concentration-dependent manner, inhibited both basal and, more potently, insulin-stimulated glucose uptake. This resulted in a negative correlation of glucose uptake and 45calcium efflux (r > 0.95, P < 0.001). This effect was approximately 5 times greater for caffeine than for 4-chloro-m-cresol, suggesting a calcium-independent part of the glucose uptake inhibition by caffeine. In our in vitro model of cultured muscle cells, insulin appears to prevent calcium overload by both stimulating efflux and inhibiting cell storage. This effect, taken together with the observed inhibitory, inverse relationship between 45calcium efflux and glucose uptake, contributes to describing the complex insulin-calcium interplay involved in target cells.

Animals↗
PubMed2004

Removal of the protein-bound solute p-cresol by convective transport: a randomized crossover study.

BACKGROUND: Middle molecules (MMs) and protein-bound solutes are poorly removed by conventional hemodialysis (HD). Hemodiafiltration (HDF) combines convection and diffusion in a single therapy and has been shown to be superior for the elimination of several small and larger retention molecules. Information on the elimination of protein-bound solutes during convective strategies is scarce. The primary aim of this randomized crossover study is to evaluate the influence of internal filtration, postdilution HDF, and predilution HDF on removal of the protein-bound solute p-cresol. METHODS: Fourteen stable patients on regular thrice-weekly medium-flux HD therapy were assigned to 5 treatment periods of 2 weeks each for: HD with HF80(S); HD with FX80; postdilution HDF, 20 L, with FX80; predilution HDF, 20 L, with FX80; and predilution HDF, 60 L, with FX80 (all dialyzers from Fresenius Medical Care, Bad Homburg, Germany). RESULTS: As for the water-soluble solutes, elimination of p-cresol was better during HDF and increased with greater filtration volumes. Removal of beta2-microglobulin (beta2m) also was enhanced during HDF. However, the positive effect of convection was offset when high predilution substitution volumes were applied, probably as a result of dilution. Within each dialytic approach, removal of the MM beta2m and the protein-bound solute p-cresol was significantly less than that of the water-soluble molecules urea nitrogen and creatinine. CONCLUSION: Our data indicate that convection can provide superior protein-bound solute removal compared with high-flux HD. Our findings also suggest that better elimination of the unbound fraction is the most plausible underlying mechanism.

Aged↗
PubMed2002

Functional properties of EGFP-tagged skeletal muscle calcium-release channel (ryanodine receptor) expressed in COS-7 cells: sensitivity to caffeine and 4-chloro-m-cresol.

We constructed and expressed in COS-7 cells, three E-green fluorescent protein (EGFP) tagged recombinant skeletal muscle ryanodine receptors (RYR). EGFP was tagged to (i) the NH2-terminus (nEGFP-RYR(FL)) and to (ii) the COOH-terminus (cRYR(FL)-EGFP) of the full length RYR; we also tagged the EGFP to (iii) the NH2-terminus of a truncated version of the RYR (nEGFP-RYR(Bhat)) lacking the bulk of the protein. The fluorescent pattern EGFP with all three constructs colocalize with that of an endoplasmic reticulum (ER) membrane tracker fluorescent dye, indicating that the RYR constructs are targeted to ER membranes. Our results show that: (i) COOH-terminal tagging abolishes the sensitivity of the RYR to caffeine, whereas the presence of EGFP at the NH2-terminus does not affect caffeine sensitivity and (ii) 4-Cl-m-cresol sensitivity is lost both with the truncated nEGFP-RYR(Bhat) and the nEGFP-RYR(FL), while COOH-terminal tagging does not affect sensitivity to 4-chloro-m-cresol. The dose-response curves of caffeine-induced calcium release of nEGFP-RYR(FL) differ from those of the truncated nEGFP-RYR(Bhat). Maximal calcium release was approached at 10 mM caffeine with the nEGFP-RYR(FL), while cells expressing the nEGFP-RYR(Bhat) construct displayed a bell shaped curve and the maximal concentration for caffeine-induced calcium release was 5 mM. Equilibrium [3H]-ryanodine binding confirmed the calcium photometry data. Our results demonstrate that EGFP tagging modifies the pharmacological properties of RYR, and suggest that 4-chloro-m-cresol and caffeine act through different mechanisms and probably interact with different sites on the RYR calcium release channel.

Animals↗
PubMed1996

Gas chromatographic determination of urinary o-cresol for the monitoring of toluene exposure.

A sensitive and reproducible gas chromatographic procedure for the quantitative determination of urinary o-cresol is described. The first step involves acid hydrolysis (2N HCl, 100 degrees C, 10 min), which yields unconjugated o-cresol. After extraction (methylene chloride, pH 2), the organic layer is concentrated by evaporation and samples are analyzed by gas chromatography-flame ionization detection with a DB-5 column (30 m x 0.25 mm, 0.25 microns). Initial oven temperature is set at 30 degrees C for 12 min and the increased 2 degrees C/min to 93 decrees C. 3,4-Dimethylphenol is used as the internal standard. The detection limit of the method is 0.36 mumol/L (1 microL injection). Additional validation data were obtained by analysis of urine samples collected from volunteers exposed to various concentrations of toluene: 10, 20, 30, 50, and 100 ppm over 7 h. Urinary o-cresol concentrations (0-3, 3-7, 7-24, and 0-24 h) were highly correlated with toluene exposure.

Chromatography, Gas↗
PubMed1980

Evidence for isofunctional enzymes used in m-cresol and 2,5-xylenol degradation via the gentisate pathway in Pseudomonas alcaligenes.

Study of the reaction sequence by which Pseudomonas alcaligenes (P25X1) and derived mutants degrade m-cresol, 2,5-xylenol, and their catabolites has provided indirect evidence for the existence of two or more isofunctional enzymes at three different steps. Maleylpyruvate hydrolase activity appears to reside in two different proteins with different specificity ranges, one of which (MPH1) is expressed constitutively; the other (MPH11) is strictly inducible. Two gentisate 1,2-dioxygenase activities were found, one of which is constitutively expressed and possesses a broader specificity range than the other, which is inducible. From oxidation studies with intact cells, there appear to be two activities responsible for the 6-hydroxylation of 3-hydroxybenzoate, and again a broadly specific activity is present regardless of growth conditions; the other is inducible by 3-hydroxybenzoate. Three other enzyme activities are also detected in uninduced cells, viz., xylenol methylhydroxylase, benzylalcohol dehydrogenase, and benzaldehyde dehydrogenase. All apparently possess broad specificity. Fumarylpyruvate hydrolase was also detected but only in cells grown with m-cresol, 3-hydroxybenzoate, or gentisate. Mutants, derived either spontaneously or after treatment with mitomycin C, are described, certain of which have lost the ability to grow with m-cresol and 2,5-xylenol and some of which have also lost the ability to form the constitutive xylenol methylhydroxylase, benzylalcohol dehydrogenase, benzaldehyde dehydrogenase, 3-hydroxybenzoate 6-hydroxylase, and gentisate 1,2-dioxygenase. Such mutants, however, retain ability to synthesize inducibly a second 3-hydroxybenzoate 6-hydroxylase and gentisate 1,2-dioxygenase, as well as maleylpyruvate hydrolase (MPH11) and fumarylpyruvate hydrolase; MPH1 was still synthesized. These findings suggest the presence of a plasmid for 2,5-xylenol degradation which codes for synthesis of early degradative enzymes. Other enzymes, such as the second 3-hydroxybenzoate 6-hydroxylase, gentisate 1,2-dioxygenase, maleylpyruvate hydrolase (MPH1 and MPH11), and fumarylpyruvate hydrolase, appear to be chromosomally encoded and, with the exception of MPH1, strictly inducible.

Alcohol Oxidoreductases↗