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PubMed1977

Local and systemic effects of commonly used cutaneous agents: lifetime studies of 16 compounds in mice and rabbits.

A number of commonly used external agents were applied repeatedly on the skin of the mouse and rabbit. These chemicals, components of commercially available products included 4-hydroxyanisole, benzalkonium chloride, bromodeoxyuridine, iododeoxyuridine, 5-nitroacenaphthene, N-N-diethyltoluamide, hexachlorophene, para-aminobenzole acid, benzophenone, isopropylmyristate, pyrogallol, resorcinol and ethylhexanediol. Also tested were a commercial hairspray, a dandruff shampoo and an anti-dandruff agent. Local and systemic changes were studied and the tumour incidence compared with that of an effective carcinogen, 9,10-dimethylbenz(a)anthracene. The mice showed no local toxic changes or tumour formation and the systemic tumour incidence, i.e., tumours of the liver, lungs, lymphatic system and other organs, was similar to that of control animals. In rabbits, a number of proliferative, benign and malignant ear tumours were observed in the positive controls, thereby demonstrating the efficacy of this model. Local toxic changes were seen in benzalkonium- and hexachlorophene-treated animals, but no skin tumours. Four animals had uterine tumours. In addition, one lung and one kidney tumour, unrelated to the method of treatment, were seen.

Administration, Topical↗
PubMed1980

alpha- and beta-Adrenoceptor activities of norepinephrine analogues in isolated tissues of the rat.

A range of norepinephrine analogues has been studied in rat tracheal, atrial, and aortic preparations. Isopropyl appeared to be the most favorable N-substituent for agonist action on tracheal adrenoceptors, whereas hydroxyphenylisopropyl gave highest activity on atrial adrenoceptors. Selectivity for the beta 2-adrenoceptor was improved with tertiary branching at the gamma-carbon and further increased by aromatic substitution with resorcinol or saligenin. Alpha-Adrenoceptor properties were substantially modified by N-substitution, whereas aromatic substitution was an important factor in determining beta-adrenoceptor agonist or antagonist activity at the beta-adrenoceptor. The data were consistent with norepinephrine analogues having multiple sites of attachment to the receptor membrane influencing receptor potency and selectivity. The data also suggest that compounds of this type can have actions on both alpha- and beta-adrenoceptors.

Adrenergic alpha-Antagonists↗
PubMedDate not supplied

Isolation and characterization of metaproterenol-3-O-sulfate: a conjugate of metaproterenol in human urine.

Metaproterenol (1-(3,5-dihydroxyphenyl)-2-isopropylaminoethanol) is primarily converted in humans to metaproterenol-3-O-sulfate following oral administration. Ion exchange column chromatography with a gradient of ammonium acetate buffer permitted the isolation of the ammonium salt of metaproterenol-3-O-sulfate from human urine. Treatment of aliquots of the column eluate with purified sulfatase and subsequent HPLC/fluorescence analysis confirmed the presence of metaproterenol. Comparison of the column eluate with a metaproterenol standard by 250-MHz proton-NMR revealed a pattern consistent with monosubstitution of the resorcinol ring. Negative and positive ion fast atom bombardment/mass spectrometry showed the metabolite to have a (M-H)- m/z of 290 and a (M + H)+ m/z ion of 292. These three methods support the structural assignment of metaproterenol-3-O-sulfate. Enzymatic hydrolysis of urine specimens from 29 different subjects with purified beta-glucuronidase as well as beta-glucuronidase-sulfatase mixtures yielded no significant increase in metaproterenol beyond purified sulfatase-treated urine, thus ruling out the presence of a glucuronide of metaproterenol. Approximately 40% of an oral 20-mg dose, given as either a tablet or a solution, was recovered in the urine as metaproterenol-3-O-sulfate. Approximately 5% of the dose was recovered in the unconjugated form. The majority of the dose was excreted over the first 12 hr with a biological half-life of 5-6 hr followed by a slower excretion phase with a half-life of 20 hr.

Chromatography, High Pressure Liquid↗
PubMed1983

Sialoglycolipids in Trypanosoma cruzi.

Mild oxidation of epimastigote forms of T.cruzi followed by sodium borotritide reduction incorporates radioactivity into glycolipid fractions. Column chromatography on silica gel of the chloroform:methanol (2:1) extract separated two main peaks of radioactivity. Treatment with neuraminidase released 30% and 18% of the radioactivity, respectively. Paper chromatography showed peaks of radioactivity with relative migration to NANA7 of 1.33 in fraction A and 1.33 and 1.51 in fraction B. When unlabeled cells were submitted to a Folch extraction, thin layer chromatography of the upper phase showed at least two components detected with the resorcinol-copper reagent. Enzymatic and mild acid hydrolysis released a sialic acid with a migration relative to NANA of 1.22. These results suggest that a substituted sialic acid is present in glycolipids of the epimastigote form of T.cruzi.

Animals↗
PubMed1984

Mercurial-promoted Zn2+ release from Escherichia coli aspartate transcarbamoylase.

The release of Zn2+ from aspartate transcarbamoylase (ATCase; c6r6) upon challenge by p-hydroxymercuriphenylsulfonate (PMPS) has been studied using the sensitive, high-affinity metallochromic indicator 4-(2-pyridylazo)resorcinol at pH 7.0. When the--SH group of each catalytic (c) chain is protected, 1 Zn2+ is released for every 4 eq of PMPS added to ATCase during titration of the 24--SH groups of regulatory (r) chains. Moreover, the release of Zn2+ is a linear function of PMPS added, indicating that the rate-limiting step in Zn2+ release is mercurial attack on the 1st of the 4 r--SH groups bonded tetrahedrally to Zn2+ in an r chain near c:r contacts. Dissociation of ATCase is linked to Zn2+ release and mercaptide formation; e.g. upon addition of 4 eq of PMPS to ATCase in 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (Hepes) buffer, 1/6th of ATCase is dissociated to c3 and r2 subunits at approximately 83% of the rate of Zn2+ release, with no accumulation of the c6r4 intermediate as is observed in KPO4 buffer. Adding less than or equal to 4 PMPS/ATCase, the release of Zn2+ is first-order in [PMPS] and is virtually independent of [ATCase] with an activation energy of 18 kcal/mol. With large excesses of PMPS, stopped-flow traces show a lag period followed by pseudo first-order release of Zn2+ from ATCase and the reaction order in [PMPS] = approximately 1.3. Under these conditions, PMPS has a chaotropic effect on ATCase; the activation energy for Zn2+ release is much lower than that obtained with limiting PMPS and is increased by the presence of phosphate or active-site ligand from 6.6 to approximately 12 kcal/mol. A reasonable explanation of the observed kinetic data is that the organomercurial reagent binds reversibly to nitrogenous side chain groups in an ATCase molecule prior to the rate-limiting reaction with a sulfhydryl group.

Aspartate Carbamoyltransferase↗
PubMed1984

Combined measurement and significance of lipid-bound sialic acid and carcinoembryonic antigen in detection of human cancer.

We evaluated the clinical usefulness of lipid-bound sialic acid (LSA) as a "tumor marker" and assessed individual and carcinoembryonic antigen (CEA) in cancer patients. Serum LSA and CEA concentrations were measured by the resorcinol method after total lipid extraction and isolation of the sialolipid fraction, and by Abbott enzyme immunoassay procedures, respectively. Results indicate that the frequency of elevation and mean LSA values were highest in patients with lung cancer (318 mg/liter), intermediate in miscellaneous (210 mg/liter) and colorectal cancers (200 mg/liter), and lowest in breast cancer (175 mg/liter); while mean CEA values were highest in colorectal cancer (162.5 micrograms/liter), followed by lung (33.8 micrograms/liter), miscellaneous (30.3 micrograms/liter), and breast cancers (11.6 micrograms/liter). Statistically, LSA and CEA values for cancer patients were significantly (P less than 0.001) higher than for normal subjects. The combined measurement of LSA and CEA in serum provides better detection potential for cancer patients than either of the two markers alone.

Adult↗
PubMed1984

[Overview of the allergens from several feeder regions of Czechoslovakia. Incidence and prevalence of contact hypersensitivity caused by the allergens spread by the population of the feeder areas of Bratislava, Trnava and Banská Bystrica 1978-1980].

With the aid of patch tests an investigation involving 3060 patients was carried out to register the incidence and prevalence of allergens of the standard and supplementary test series. The standard series with 16 allergens was selected in cooperation with the work group for curtailing contact dermatitis and occupational dermatoses in the socialist countries. The Czechoslovakian supplementary test series included three allergens: neomycin sulfate, extr . chamomillae and resorcinol. In 22.6% of the 693 patients the skin tests were positive for at least one allergen. The most frequent eczematogenic among men was potassium dichromate (resulting from contact with cement), among women nickel sulfate, and in the group as a whole Peruvian balm. The age groups most affected were between 41 and 50 years and between 51 and 60 years, respectively, for men, between 21 and 30 years for women, and between 21 and 30 years for the group as a whole. In registering the prevalence, chamomillae extract caused the highest occurrence among men, cobalt nitrate among the women, and also cobalt nitrate for the group as a whole. The age group affected most was between 51 and 60 years. In the complete investigative study of incidence and prevalence, Peruvian balm topped the list for the group as a whole, potassium dichromate for the men, and nickel sulfate for the women. Among the men and for the group as a whole the most affected age group was between 51 and 60 years, and among the women between 21 and 30 years.(ABSTRACT TRUNCATED AT 250 WORDS)

Adult↗
PubMed1983

The mechanism of oxidation of nitroalkanes by horseradish peroxidase.

Horseradish peroxidase catalyzes the anaerobic oxidation of 2-nitropropane (probably as the nitronate R-) by H2O2 via Compounds I and II to form R-R. The oxidation rate is stimulated 10-fold by O2 and the products become acetone and NO-2. The aerobic oxidation of R- is a free radical chain reaction which is initiated by peroxidase and propagated by R because (a) R-R, reasonably, must arise as 2R leads to R-R, (b) over 90% of the enzyme-initiated reaction occurs free in solution, and (c) the Km value for R- is independent of the type of initiator. We present a scheme for initiation, propagation, and termination which explains product structure, the effects of resorcinol, CN-, ascorbate, superoxide dismutase, and catalase, as well as the ping-pong reaction kinetics. We used methanenitronate to investigate the locus of electron transfer from R- into the heme moiety of the enzyme because this donor reacts with Compound II to form an isoporphyrin, which then rearranges to a modified enzyme in which the ferriheme contains the nitromethyl group in covalent linkage at a methine carbon. The modified enzyme is 30-50% as active catalytically as the native enzyme. We argue that reduction of Compound II by R- occurs at the methine carbon by two competing pathways, namely, direct one electron transfer and, at about one-half the frequency, homolytic cleavage of a covalent heme-substrate adduct (isoporphyrin).

Alkanes↗
PubMed1982

Light and electron microscopic study on the oxytalan elaunin and elastic fibers in the inferior segment of the human esophagus.

A light and electron microscopic study on oxytalan, elaunin and elastic fibers was performed in the inferior segment of the human esophagus of 30 individuals aged, from 2 months to 76 years. Paraffin sections were stained by the aldehyde-fuchsin (Gomori 1950), Orcein (Unna-Tanzer 1891), resorcinol-fuchsin (Weigert 1898) and iron-hematoxylin (Verhoeff 1908), with or without a previous oxidation by peracetic acid. For the electron microscope, the fixation was performed in a 3% glutaraldehyde solution with 0.25% of tanic acid in Millonig buffer (Futaesaku et al. 1972; Cotta-Pereira et al. 1975, 1976). A subepithelial network of oxytalan fibers (fibrotubular bundles) without direct connections with the BM and indirectly related to this one through periodical reticulin like fibers, were described. More deeply the oxytalan fibers are in continuity with elaunin and these with elastic fibers, close to the LMM. The TSs and the TA are essentially formed by elastic fibers and by relatively scanty presence of elaunin ones. From the TM and probably from the LMM, among the muscle cells, oxytalan fibers gradually change to elaunin and these to elastic fibers toward the connective tissue septa situated among muscle bundles and connective layers (LPM, TSm and TA (or TSs). A fibrilar (fibrotubular) "continuum" is here admitted, extending from the TA to the subepithelial BM with a variable amount of elastin like material, according to the layer they belong. They change progressively from oxytalan to elastic fibers, passing through an intermediate phase of elaunin fibers.

Adolescent↗
PubMed1981

Plasma lipid-bound sialic acid and carcinoembryonic antigen in cancer patients.

We evaluated lipid-bound sialic acid as a "marker" in cancer patients and assessed the individual and combined value of lipid-bound sialic acid and carcinoembryonic antigen determinations in these patients. Plasma was sampled from 62 normal subjects and 125 cancer patients. Lipid-bound sialic acid was determined by the resorcinol method after total lipid extraction and isolation of the sialolipid fraction from plasma. Neither marker was increased in many breast cancer patients. Carcinoembryonic antigen was increased more commonly and to a greater degree in colon cancer patients and seems to be the preferred marker. Both markers were increased in lung cancer patients and their combined evaluation improved the rate of detection. Lipid-bound sialic acid was increased in more patients with leukemias, lymphomas, Hodgkin's disease, and melanomas, suggesting that it may be a useful biochemical marker in these types of cancer.

Breast Neoplasms↗
PubMedDate not supplied

[Utilization of aromatic compounds by yeasts of the genus Debaryomyces].

The ability to utilize phenol, catechol, resorcinol, hydroquinone, p-hydroxybenzoic acid, m-hydroxybenzoic acid, 2,4-dihydroxydenzoic acid, protocatechuic and gentisic acids was studied among 61 strains of 23 yeast species belonging to the Debaryomyces genus. All species characterized by active fermentation did not utilize these aromatic compounds. If fermentation was absent or weak, some of the aromatic compounds were utilized. This fact suggests an ecological difference between the two above yeast groups, justifying the subdivision of the Debaryomyces genus by some authors into two genera Debaryomyces and Torulaspora. No correlation could be established between the utilization of certain aromatic compounds and the yeast species classified on the basis of their behaviour toward carbohydrates. Therefore, classification of yeasts belonging to the Debaryomyces genus is artificial. It would be expedient to isolate a small number of typical species unless a more accurate relationship is established between cultures of the Debaryomyces genus referred to as different species.

Ascomycota↗
PubMed1994

Dominance of metallothionein in metal ion buffering in yeast capable of synthesis of (gamma EC)nG isopeptides.

The relationship of yeast metallothionein (MT) and (gamma EC)nG isopeptides (phytochelatins) in metal ion buffering was assessed. The effect of constitutive expression of yeast metallothionein (MT) genes on accumulation of metal-(gamma EC)nG isopeptide (phytochelatin) complexes was analyzed in Candida glabrata and Schizosaccharomyces pombe cultures incubated in the presence of cadmium salts. Constitutive expression of the Saccharomyces cerevisiae MT (CUP1) gene inhibited the accumulation of metal-phytochelatin complexes in both C. glabrata and S. pombe. Intracellular Cd(II) sequestration occurred by formation of CdMT complexes. Phytochelatin (gamma EC)nG complexes appear to function in metal buffering in cells when MT genes are not present or expressed. A third condition in which metal-(gamma EC)nG complexes are observed is when constitutively expressed MT does not accumulate. We observed that C. glabrata lacking the AMT1 gene necessary for copper induction of the MT genes expressed MTII constitutively, but this expression does not lead to CdMTII accumulation. Only Cd-(gamma EC)nG complexes accumulate. Likewise, metal exposed cultures of S. cerevisiae (cup1) transformed with C. glabrata MTII under the constitutive ADH1 promoter resulted in constitutive expression of MTII and accumulation of CuMTII complexes but no CdMTII complexes. The inability of constitutively expressed C. glabrata MTII to buffer Cd(II) ions may arise in part from an inherent kinetic lability of CdMTII complexes. Incubation of ZnMTII with a metallochromic chelator, 4-(2-pyridylazo)resorcinol resulted in greater Zn(II) loss than Zn(II) complexes with CUP1 MT and C. glabrata MTI. C. glabrata MTII appears to be the first MT described which forms an unstable Cd(II) complex.

Binding Sites↗
PubMed1994

Increased GD3 ganglioside in plasma of children with T-cell acute lymphoblastic leukemia.

The presence of tumor-associated GD3 in the plasma of 12 patients with T-cell acute lymphoblastic leukemia (T-ALL) was determined utilizing microscale ganglioside isolation and thin layer chromatography (TLC) immunodetection with an anti-GD3 monoclonal antibody, R24. Immunostaining of control plasma gangliosides revealed two nearly equal subspecies groups of GD3, GD3U and GD3L. Plasma from those T-ALL patients with a high R24-positive lymphoblast count (> 60,000/mm3) had a significant increase in total GD3 and each of the GD3 subspecies groups, and a disproportionate increase in GD3L resulted in an increased ratio GD3L/GD3U in these samples. In contrast, total GD3, GD3 subspecies, and GD3L/GD3U was not increased in plasma from those cases with low R24-positive blast count (< 20,000/mm3) or in pre-B ALL plasma. The altered GD3 content in R24-positive T-ALL plasma was reversible, since total GD3 and GD3L/GD3U in plasma from a patient in remission from R24-positive T-ALL was near that of controls. Resorcinol staining of TLC-separated gangliosides confirmed the results observed with R24 detection methods. The results strongly suggest that GD3 is shed in vivo from T-ALL blasts in patients with R24-positive T-ALL, resulting in both qualitative and quantitative changes in circulating GD3 in these patients.

Biomarkers, Tumor↗
PubMed1993

Chemical modification and mutagenesis studies on zinc binding of aminoacyl-tRNA synthetases.

Thermus thermophilus methionyl-tRNA synthetase consists of two identical subunits with a potential Zn(2+)-binding sequence of Cys-X2-Cys-X13-Cys-X2-His (Nureki, O., Muramatsu, T., Suzuki, K., Kohda, D., Matsuzawa, H., Ohta, T. Miyazawa, T., and Yokoyama, S. (1991) J. Biol. Chem. 266, 3268-3277). Upon chemical modification of the 3 Cys residues of T. thermophilus MetRS with sodium p-(hydroxymercuri)phenylsulfonate, one Zn2+ ion was released from one subunit of the molecule, as monitored with 4-(2-pyridylazo)resorcinol. Site-directed mutagenesis of Cys and His residues in the Zn(2+)-binding sequence reduced the aminoacylation activity; the kcat value was markedly decreased, and the Km values for L-methionine and tRNAf(Met) were increased. Similarly, Cys modification released two Zn2+ ions from T. thermophilus and Escherichia coli isoleucyl-tRNA synthetases and E. coli threonyl-tRNA synthetase, which have Zn(2+)-binding motifs, and impaired their activities. By contrast, three other aminoacyl-tRNA synthetases that lack Zn(2+)-binding motif neither released Zn2+ ion nor lost their activities upon Cys modification. These results indicate that the Zn(2+)-binding sequences are important for catalysis and recognition in the aminoacylation reactions of a subgroup of aminoacyl-tRNA synthetases.

Acylation↗
PubMed1993

T4-phage deoxycytidylate deaminase is a metalloprotein containing two zinc atoms per subunit.

Deoxycytidylate (dCMP) deaminase, a hexameric allosteric enzyme induced on infection of Escherichia coli by bacteriophage T4, was shown to contain two atoms of zinc per subunit by atomic absorption spectroscopy. One zinc appears to be involved in catalysis, as described for adenosine deaminase (Sharaff, A. J., Wilson, D. K., Chang, Z., and Quiocho, F. A. (1992) J. Mol. Biol. 226, 917-921) and cytidine deaminase (Yang, C., Carlow, D., Wolfenden, R., and Short, S. A. (1992) Biochemistry 31, 4168-4174). This thesis is supported by the finding that the enzyme loses about 80% of its activity in the presence of o-phenanthroline. It has also been found that zinc is released when the enzyme is denatured in the presence of the metallochromic indicator, 4-(2-pyridylazo)resorcinol. Renaturation of the deaminase to an active form occurred in the presence but not in the absence of zinc. The second atom of zinc is proposed to be located in a region of T4-dCMP deaminase that resembles a zinc finger. This region, which has the sequence His-X3-Cys-X14-His-X3-His, would represent a zinc-binding motif that has not been described previously.

Amino Acid Sequence↗
PubMed1977

Improved colorimetric determination of serum zinc.

We show how zinc may easily be quantified in serum by first using an optimum concentration of guanidine hydrochloride to cause release of zinc from proteins, followed by complexation of released metals with cyanide. The cyanide complex of zinc is preferentially demasked with chloral hydrate, followed by a colorimetric reaction between zinc and 4-(2-pyridylazo)resorcinol. This is a sensitive water-soluble ligand; its complex with zinc has an absorption maximum at 497 nm. Values found by this technique compare favorably with those obtained by atomic absorption spectroscopy.

Bilirubin↗
PubMed1996

Quantification of gangliosides by microbore high performance liquid chromatography.

A highly sensitive analytical method was developed that allows the separation of ganglioside mixtures and quantification of individual non-derivatized gangliosides in the concentration range between 2 pmol and 1 nmol. Gangliosides were separated with a gradient of acetonitrile/phosphate buffer on a 1 mm diameter microbore HPLC column packed with Spherisorb-NH2. They eluted according to their number of sialic acid residues with increasing phosphate and decreasing acetonitrile concentrations. The separation of different gangliosides with equal sialic acid content is also described. The column effluent was monitored at the maximum of absorption at 197 nm. The sensitivity is higher than resorcinol staining of fractionated gangliosides by thin layer chromatography, previously the standard method for ganglioside analysis. The separated gangliosides can be analyzed by further methods. The HPLC method described here has been applied to the analysis of serum and oligodendroglioma specimens.

Chromatography, High Pressure Liquid↗
PubMed1996

[Artificial models of transport proteins in membrane].

Artificial molecules were designed to mimic membrane transport proteins which produce large and selective ion fluxes across biological membrane with functions of flux-control. Several amphiphilic lipid molecules were assembled in bilayer lipids to make supramolecular ion channels which gave single ion channel currents across planar lipid bilayers. Stable and constant conductance levels were observed with transitions between open and closed states. Unimolecular channels were also designed by using macrocyclic resorcinol tetramer, calix [6] arene or cyclodextrin. These unimolecular channels gave a single conductance and a sharp ion selectivity. All these channels were cation selective over anion. Ionic currents was successfully modulated by the application of membrane potential or photochemical isomerization.

Carrier Proteins↗