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PubMed1977

[Food additives and their possible genetic toxicity; microbiological determination].

In the present work we intend to find an accurat methodology to establish in an easy way the mutagenic potential of drugs employed as food additives. For that purpose we first selected a microbiological system for performing this assay. The method assayed consisted of investigating the effect exerted on genetic recombination by the following chemical agents: Chloroacetic Acid, Iodoacetic Acid, Sorbic Acid, Potassium Metabisulfite, Sodium Nitrite, Auramine and Erythrossine. The activity of these agents was detected though their effect on the transformation of an auxotrophic strain of Bacillus subtilis. Comparative assays of reversion of characters have been made with strains of Salmonella typimurium already used by other authors. These assays have also been repeated with several auxotrophic strains of Bacillus subtilis and different genetic characters have been studied. Most results suggest that changes in the recombination process should have occured at different levels according with the drugs assayed. On the other hand, the results of reversion have not been significant enough. We think that more accuracy is afforded by both the recombination and the reversion assay developed to other for this kind of detection.

Animals↗
PubMedDate not supplied

Classification of acute myeloid leukaemia in trephine biopsies with special reference to lactoferrin.

In spite of advances in immunohistochemical techniques, the histological subclassification of acute myeloid leukaemia (AML) in bone marrow biopsy has remained difficult. In particular, the translation of the diagnostic criteria of the French-American-British (FAB) cooperative group as primarily defined by bone marrow cytology into histology poses considerable problems. In this study, we investigated the expression of lactoferrin (LF) in various subtypes of AML and studied the usefulness of its immunohistochemical detection combined with a panel of antibodies directed against myeloperoxidase (MPOX), lysozyme (LYS), CD34 and naphthol-AS-D-chloroacetate esterase (NACE) staining in solving this problem. Trephine biopsies of 52 cases of AML were selected for histological evaluation in comparison to bone marrow aspirates classified according to FAB (M1 n = 10, M2 n = 7, M3 n = 11, M4 n = 13 and M5 n = 11). The results obtained confirmed the specificity of LF as a marker for secondary granules in neutrophilic myeloid cells and as a tool to subclassify AML. Its parallel application with (immuno-)staining for MPOX, LYS and NACE has allowed the identification of M1, M3, M5 cases, where there LF is lacking. Typically M2 is characterized by a subpopulation of LF-positive cells which tend to display a myelocytic differentiation. However, M4 shows a heterogeneous expression pattern of LF: M4a may be defined as more immature variant without LF expression while in M4b a more mature myeloid subpopulation stains positive for LF.

Adult↗
PubMedDate not supplied

Phase III interlaboratory study of FETAX. Part 3. FETAX validation using 12 compounds with and without an exogenous metabolic activation system.

FETAX (Frog Embryo Teratogenesis Assay-Xenopus) is a 96-h whole-embryo developmental toxicity screening assay that can be used in ecotoxicology and in detecting mammalian developmental toxicants when an in vitro metabolic activation system is employed. A standardized American Society for Testing and Materials (ASTM) guide for the conduct of FETAX has been published, along with a companion atlas that helps in embryo staging and in identifying malformations. As part of the ASTM process, an interlaboratory validation study was undertaken to evaluate the repeatability and reliability of FETAX and to evaluate the potential teratogenic hazard of 12 compounds. Three different laboratories participated in the study. All three participating laboratories had extensive experience with the assay. FETAX intralaboratory and interlaboratory variability, as judged by coefficients of variation, were very low. Potential teratogenic hazard was evaluated using two major criteria from FETAX experiments employing metabolic activation systems (MAS). These were the teratogenic index TI (TI = 96-h lc(50)/96-h ec(50) (malformation)) and the minimum concentration that inhibits growth (MCIG). A compound was considered teratogenic by this criterion when the MCIG was significantly different from controls at concentrations below the 30% level of the MAS 96-h lc(50). Based on the results of this and other studies, a decision table was constructed in order to evaluate additional studies. Severity of malformations caused, especially near the MAS 96-h ec(50) (malformation), were also evaluated. Four compounds were non-teratogenic but two compounds were clearly teratogenic. The remaining six compounds were ranked as equivocal teratogens. The results were discussed in light of the difficulty of producing an adequate decision table. FETAX proved to yield repeatable and reliable data as long as care was taken during range-finding and technicians were adequately trained. The MAS was essential in using FETAX to predict developmental hazard in mammals, and still requires further development.

Acetates↗
PubMed2005

A study on the influence of the structure of the glycosyl acceptors on the stereochemistry of the glycosylation reactions with 2-azido-2-deoxy-hexopyranosyl trichloroacetimidates.

The stereochemical outcome of glycosylations with 2-azido-2-deoxy-D-gluco- and D-galactopyranosyl trichloroacetimidates as glycosyl donors has been investigated by using a series of chiro-inositol derivatives as glycosyl acceptors. The influence of the absolute configuration, the conformation and the conformational flexibility of the glycosyl acceptor has been studied by using different glycosyl donors under similar pre-established experimental conditions. Although the structure of the acceptor may play a role in governing the stereochemistry of these glycosylations, the results show that, in general terms, the relative influence of these factors is difficult to evaluate. For a given set of experimental conditions, the stereochemical course of these glycosylations depends on structural features of both glycosyl donor and glycosyl acceptor. It is a balance of these factors, where the structure of the glycosyl donor always plays a major role, which determines the stereochemistry of the coupling reaction. Therefore, the examples reported in the literature in which the structure of the glycosyl acceptor appears to be crucial in determining the stereochemistry of the reaction constitute particularly favorable cases which do not presently allow any further generalization.

Azides↗
PubMed2006

Solid-phase oligosaccharide synthesis of a small library of N-glycans.

Solid-phase oligosaccharide synthesis is based on a hydroxymethylbenzyl benzoate spacer linker which is connected to the Merrifield resin (1 P). Glycosylation was performed with O-glycosyl trichloroacetimidates of glucosamine, mannose, and galactose permitting chain extension (2e, 5e), branching (4b, 7b, 8b), and chain termination (3t, 6t, 9t) with the use of O-benzyl, O-benzoyl, and N-dimethylmaleoyl as permanent and O-fluorenylmethoxycarbonyl (Fmoc) and O-phenoxyacetyl (PA) as temporary protecting groups. The steps required on solid phase are i) glycosylation under TMSOTf catalysis, ii) selective cleavage of the temporary protecting groups, Fmoc with NEt3 and PA with 0.5 equivalents of NaOMe in CH2Cl2/MeOH, and iii) product cleavage from the resin with 4.0 equivalents of NaOMe in CH2Cl2/MeOH and following O-acetylation for convenient product isolation. Thus a highly successful synthesis of a small library of seventeen N-glycan structures was made possible comprising the N-glycan pentasaccharide core structure 53 and two further chain extended hexa- and heptasaccharide N-glycans with a glucosamine or a lactosamine residue, respectively, which is attached to one of the mannose residues of the core structure (56 and 59).

Benzoates↗
PubMed1996

Negative staining of proteins in polyacrylamide gels with methyl trichloroacetate.

This paper describes a new, sensitive (in the nanogram range), and rapid (two-step) technique for the negative staining of proteins in polyacrylamide gels in the presence or absence of sodium dodecyl sulfate. After separation, gels are incubated with 8% methyl trichloroacetate ester in 38% isopropanol and then washed in water to produce a negative image of colorless proteins against an opaque background. The technique allows unmodified proteins to be recovered for biological studies or transblot for amino acid sequence. Finally, owing to the reversibility of the process, gels can be restained after rapid visualization. For these reasons, negative staining with methyl trichloroacetate should become the method of choice for rapid and sensitive staining of proteins prior to further processing, including stable staining with silver ions.

Chemical Precipitation↗
PubMed1993

Effect of dose on the metabolism of 1,1,2,2-tetrabromoethane in F344/N rats after gavage administration.

1,1,2,2-Tetrabromo[U-14C]ethane ([14C]TBE) was used to study the metabolism of TBE in rats. Three graded doses of TBE (1.17, 13.6, and 123 mg/kg; 1 microCi 14C/rat at each dose) were administered by gavage to three groups of four rats each. Excreta samples were collected at various time intervals up to 96 hr. Following euthanization, 14C activity was measured in the excreta, tissues, and carcass. The fraction of the dose exhaled as volatile metabolites of TBE, excluding 14CO2, was approximately 9-10% higher in rats given the high dose of TBE compared to that in rats given either the low or the medium dose. The fraction excreted in the urine decreased with increasing TBE dosage. 1,2-Dibromoethylene and tribromoethylene were identified as exhaled metabolites at the high dose. Three major urinary metabolites were identified: dibromoacetic acid, glyoxylic acid, and oxalic acid. The results of this study indicate that the metabolism of TBE was linear up to a dose of 13.6 mg/kg, but the contribution of various TBE metabolic pathways was different at a dose of 123 mg/kg.

Acetates↗
PubMed1995

Trichloroethene-induced autoimmune response in female MRL +/+ mice.

Trichloroethene (TCE) has been implicated in the pathogenesis of autoimmune diseases such as systemic lupus erythematosus (SLE) and scleroderma in humans. However, experimental studies have not been conducted to establish the role of TCE in causing autoimmunity and/or SLE. To clarify the role of TCE in autoimmune responses, subchronic studies were carried out in female autoimmune prone mice (MRL +/+). Three groups of mice (5 weeks old) received intraperitoneal injections of 10 mmol/kg of TCE, 0.2 mmol/kg of dichloroacetyl chloride (DCAC) (one of the metabolites of TCE with strong acylating property), or an equal volume (100 microliters) of corn oil alone (controls). Animals were dosed every 4th day for 6 weeks and euthanized 24 hr following the last dose. Sera and major tissues were collected and analyzed. Spleen weights in the TCE and DCAC groups increased 36% with a similar pattern of change in the spleen-to-body weight ratios. Serum IgG in the TCE and DCAC groups increased 45 and 322%, respectively. Using specific ELISA assays for mice, autoimmune antibodies were detected in the sera of TCE- and DCAC-treated mice in the following patterns: for anti-nuclear antibodies; controls, 0/4; TCE, 4/4; DCAC, 3/5; for anti-ssDNA antibodies; controls, 0/4; TCE, 2/4; DCAC, 5/5; for anti-cardiolipin antibodies; controls, 0/4; TCE, 0/4; DCAC, 3/5. An ELISA developed for the measurement of DCAC-specific antibodies using conjugated DCAC-albumin as an antigen showed the following pattern: for controls, 0/4; TCE, 0/4; DCAC, 5/5. These results suggest that TCE and its metabolite, DCAC, induce and/or accelerate autoimmune responses in female MRL +/+ mice. The greater responses induced by DCAC at a dose 50 times lower than TCE suggests that this metabolite may be important in the mechanisms leading to TCE-induced autoimmunity.

Animals↗
PubMed1995

Developmental toxicity of trichloroethylene, tetrachloroethylene and four of their metabolites in rat whole embryo culture.

The embryotoxicity of trichloroethylene (TRI), tetrachloroethylene (PER), and of four of their oxidative metabolites i.e. trichloroacetic acid, dichloroacetic acid, chloral hydrate, and trichloroacetyl chloride, was studied in vitro, using the rat whole embryo culture system. Embryos from Sprague-Dawley rats were explanted on gestational day 10 (plug day = day 0) and cultured for 46 h in the presence of the test chemical. All of the tested chemicals produced concentration-dependent decreases in growth and differentiation and increases in the incidence of morphologically abnormal embryos. TRI and PER produced qualitatively similar patterns of abnormalities, while TRI and/or PER metabolites, each elicited clearly distinguishable dysmorphogenic profiles. The presence of hepatic microsomal fractions in the culture medium produced marked decreases in TRI- and PER-induced embryotoxic effects, including mortality, severity of malformations, and delayed growth and differentiation.

Animals↗
PubMed1995

Solid-phase synthesis of a glycosylated hexapeptide of human sialophorin, using the trichloroacetimidate method.

A hexapeptide containing a beta-D-Gal p-(1-->3)-alpha-D-Gal pNAc-(1-->O)-L-threonine unit was synthesized using glycosylated pentafluorophenyl esters in an Fmoc-based strategy. In all of the glycosylation reactions, trichloroacetimidates were successfully employed. The disaccharide moiety was prepared from tetra-O-acetyl-alpha-D-galactopyranosyl trichloroacetimidate and tert-butyldimethylsilyl 2-azido-6-O-benzoyl-2-deoxy-beta-E-galactopyranoside with boron trifluoride etherate as a catalyst. The glycosylated active esters were obtained in the reaction of alpha and beta 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl-(1-->3)-4-O-acetyl-2-azid o-6- O-benzoyl-2-deoxy-D-galactopyranosyl trichloroacetimidates with Fmoc-protected pentafluorophenyl esters of L-serine and L-threonine in the presence of trimethylsilyl trifluoromethanesulfonate as Lewis acid. The glycosylated pentafluorophenyl ester of L-threonine was transformed into glycopeptides via a solid-phase synthesis. Azide reduction and N-acetylation were performed on the solid phase with a thioacetic acid-pyridine mixture. The glycopeptide was then cleaved from the resin with strong acid, also removing the acid-labile protecting groups of the peptide chain. Finally, the acyl groups used for sugar protection were cleaved with sodium methoxide, affording the completely deprotected N-acetyl-L-leucyl-L-glutamyl-O-[beta-D-galactopyranosyl-(1-->3)-2- acetamido-2-deoxy-alpha-D-galactopyranosyl]-L-threonyl-L-seryl-L-threony l- glycinamide (1) in high purity.

Acetamides↗
PubMed1987

Dichloroacetate derivatives. Metabolic effects and pharmacodynamics in normal rats.

Dichloroacetate (DCA) reduces blood glucose, lactate and lipids in diabetes or during fasting. Chronic use of DCA, however, is limited by toxicity, probably due in part to its rapid conversion to oxalate in vivo. In theory, therefore, DCA's efficacy may be retained and its toxicity minimized by controlling its rate of metabolism. We attempted to alter DCA pharmacokinetics and bioavailability by synthesizing various derivatives comprising DCA esters with polyols and DCA ionic complexes. Twenty-four hour fasted, nondiabetic rats received single, orogastric doses of saline (control) sodium DCA (100mg/kg) or the following derivatives (D1-4): the esters D1-D3: potassium tetra (dichloroacetyl) glucuronate (D1), inositol-monophosphate-tetradichloroacetate (D2), inositol-hexadichloroacetate (D3) and inositol-hexa [N-methylnicotinate] hexadichloroacetate salt (D4). Each derivative was administered at a dose that would ultimately provide 100 mg/kg DCA as the anion. All derivatives were orally effective in significantly decreasing blood glucose and lactate. D4 exerted the most potent and long-lasting glucose- and lactate-lowering effects, yet increased plasma DCA concentrations less than an equivalent dose of the sodium salt. When administered to reverse light-cycled rats, D4 markedly inhibited the incorporation of tritiated water into cholesterol and triglycerides. We conclude that derivatives of DCA retain the biological activity of the parent compound, but may exhibit different pharmacokinetics. They may eventually prove useful in the treatment of diabetes mellitus, hyperlipidemia and lactic acidosis in man.

Acetates↗
PubMed1983

Mutagenicity of dichloroacetylene and its degradation products trichloroacetyl chloride, trichloroacryloyl chloride and hexachlorobutadiene.

Dichloroacetylene (DCA) is a highly reactive compound that decomposes rapidly in contact with air into a series of chlorinated aliphatic hydrocarbons (e.g., phosgene, trichloroacetyl chloride, trichloroacryloyl chloride and hexachlorobutadiene). Experiments were performed to compare the mutagenic properties of DCA and its degradation products on the histidine-dependent tester strains TA98 and TA100 of Salmonella typhimurium. In these experiments, DCA vapour was streamed under analytical control through the bacterial suspensions. DCA is soluble in aqueous solution and was stable under the experimental steady-state conditions of the bacterial exposure. There is a linear correlation between the supply of DCA vapour and solubilized DCA in the range of 1000 and 16 000 ppm. Mutagenic response was observed with strain TA100 if the bacteria were suspended in Oxoid medium. No mutagenicity could be detected with strain TA98. DCA mixtures with acetylene, as used as stabilizer for animal experiments, were not mutagenic in either bacterial strain, irrespective of the presence or absence of S9 mix in the cell suspension. One of the degradation products of DCA, trichloroacryloyl chloride, showed pronounced mutagenic properties with and without drug-metabolizing enzymes. Other degradation products of DCA, such as trichloroacetyl chloride and hexachlorobutadiene, were not mutagenic, either in the presence or absence of liver homogenate.

Acetylene↗
PubMed2004

Synthesis of a hexasaccharide fragment of the O-deacetylated GXM of C. neoformans serotype B.

beta-D-Xylp-(1-->4)-alpha-D-Manp-(1-->3)-[beta-D-Xylp-(1-->2)]-alpha-D-Manp-(1-->3)-[beta-D-Xylp-(1-->2)]-alpha-D-Manp, the fragment of the exopolysaccharide from Cryptococcus neoformans serovar B, was synthesized as its methyl glycoside. Thus, acetylation of allyl 3-O-benzoyl-4,6-O-benzylidene-alpha-D-mannopyranoside (1) followed by debenzylidenation and selective 6-O-benzoylation afforded allyl 2-O-acetyl-3,6-di-O-benzoyl-alpha-D-mannopyranoside (4). Glycosylation of 4 with 2,3,4-tri-O-benzoyl-D-xylopyranosyl trichloroacetimidate (5) furnished the beta-(1-->4)-linked disaccharide 6. Deallylation followed by trichloroacetimidate formation gave the disaccharide donor 8, and subsequent coupling with allyl 2,3,4-tri-O-benzoyl-beta-D-xylopyranosyl-(1-->2)-4,6-di-O-benzoyl-alpha-D-mannopyranoside (9), produced the tetrasaccharide 10. Reiteration of deallylation and trichloroacetimidate formation from 10 yielded the tetrasaccharide donor 12. The downstream disaccharide acceptor 18 was obtained by condensation of 5 with methyl 3-O-acetyl-4,6-O-benzylidene-alpha-D-mannopyranoside, followed by debenzylidenation, benzoylation, and selective 3-O-deacetylation. Coupling of 18 with 12 afforded the hexasaccharide 19, and subsequent deprotection gave the hexasaccharide glycoside 20. Selective 2"-O-deacetylation of 19 gave the hexasaccharide acceptor 21. Condensation of 21 with glucopyranosyluronate imidate 22 did not produce the expected heptasaccharide glycoside; instead, a transacetylation product 19 was obtained. Meanwhile, there was no reaction between 21 and the bromide donor 23.

Acetamides↗
PubMed2004

Facile synthesis of arabinomannose penta- and decasaccharide fragments of the lipoarabinomannan of the equine pathogen, Rhodococcus equi.

Pentasaccharide repeating unit 20 of the lipoarabinomannan from the equine pathogen, Rhodococcus equi, and its dimer 31, were synthesized. The pentasaccharide was obtained by assembling a benzoylated 2,6-branched mannosyl trisaccharide acceptor 13 with a free hydroxyl group at C-2' of the mannose residue attached to the core mannose residue by (1 --> 6)-linkage, followed by coupling with 2,3,5-tri-O-benzoyl-alpha-D-arabinofuranosyl-(1 --> 2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (18), and by deacylation. Meanwhile, the decamer 31 was obtained by firstly preparing a benzoylated mannose (1 --> 6)-linked tetrasaccharide backbone 26 with 2-, 2"-O-ClAc, and 2'-, 2'''-O-Ac groups, respectively, then by dechloroacetylation and subsequent condensation with perbenzoylated trichloroacetimidate, and then by deacetylation and subsequent coupling with 18, and finally, by deacylation.

Acetamides↗
PubMed2005

Synthesis of a glycolipid for studying mechanisms of mitochondrial uncoupling proteins.

Glucose-O-omega-palmitic acid is an amphipathic molecule that is useful as a tool for studying the mechanism of mitochondrial uncoupling proteins. The synthesis of this glycolipid is described herein. The study of the reaction of a series of glycosyl donors with appropriate acceptors derived from 16-hydroxyhexadecanoic acid showed that a glycosyl trichloroacetimidate donor was more efficient than thioglycoside, glycosyl halide and glycosyl acetate donors for synthesis of this glycolipid.

Acetamides↗