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PubMed1975

[Eosinophilic leukaemia with chloroacetate-esterase-positive granules in a child (author's transl)].

Eosinophilic leukaemia was diagnosed in a 13-year-old boy with clinical and haematological signs of acute leukaemia. A positive naphthol-AS-D-chloroacetate esterase reaction was present in 93% of bone marrow eosinophils. This confirms earlier findings for this sub-group of leukaemia in adultsmcharcot-Leyden's crystals were found in bone marrow, and the eosinophils were further characterized by other cytochemical and electronmicroscopic studies. Only short remission periods were achieved, the patient dying 53 weeks after diagnosis. Attacks of cardiac arrhythmias, thought to be due to adriamycin treatment, were probably related to thrombi in the coronary arteries as a result of disseminated intravascular coagulation. It is thought that eosinophilic leukaemia with a positive naphthol-AS-D-chloroacetate esterase reaction is a variant of acute myeloid leukaemia.

Acute Disease↗
PubMed2000

Racemic and chiral 1-[N-(chloroacetyl)carbamoylamino]-2, 3-dihydro-1H-inden-2-yl chloroacetate.

In the racemic crystals of (1S,2R)- or (1R, 2S)-1-[N-(chloroacetyl)carbamoylamino]-2,3-dihydro-1H-inden- 2-yl chloroacetate, C(14)H(14)Cl(2)N(2)O(4), (I), the enantiomeric molecules form a dimeric structure via the N-H.O cyclic hydrogen bond of the carbamoyl moieties. In the chiral crystals of (-)-(1S, 2R)-1-[N-(chloroacetyl)carbamoylamino]-2,3-dihydro-1H-inden- 2-yl chloroacetate, C(14)H(14)Cl(2)N(2)O(4), (II), the N-H.O intermolecular hydrogen bond forms a zigzag chain around the twofold screw axis. The melting points and calculated densities of (I) and (II) are 446 and 396 K, and 1.481 and 1.445 Mg m(-3), respectively.

Journal Article↗
PubMed1996

Monoclonal antibody WGM1 directed against proteinase 3: an immunohistochemical marker for naphthol ASD chloroacetate.

Enzyme histochemistry for naphthol ASD chloroacetate (NASDCA, 'Leder's stain') is used to identify the granulocyte lineage ranging from promyelocytes to mature neutrophils and is an additional tool for the characterization of leukemias. We demonstrated for the first time that NASDCA activity can be detected by routine immunohistochemistry and immunocytochemistry using the monoclonal antibody WGM1 directed against proteinase 3 (PR3; synonyms: Wegener's autoantigen, myeloblastin). Immunohisto- and immunocytochemical staining with WGM1 against PR3 and enzyme histochemistry for NASDCA produced identical staining patterns in normal myelomonocytic cells and cells of myeloid leukemia. This was additionally proven by double immunostainings. We have also shown that PR3 is one of the specific proteinases responsible for hydrolysis of NASDCA.

Adolescent↗
PubMed1977

[Products of a reaction between 1H-indazol-3-ol and ethyl chloroacetate].

Ethyl esters of [(1-carbethoxymethyl-1H-indazol-3-yl)oxy]-acetic acid; (2-carbethoxy-3,4-dihydro-4-oxo-3-quinazolinacetic acid; [(1H-indazol-3-yl)oxy] acetic acid; o.aminoippuric acid; (2-carbethoxy-4-oxo-1,2,3,4--tetrahydro)-3-quinazolin acetic acid; (3-hydroxy-1H-indazol-1-yl)acetic acid; (1H-indazol-3-on-2-yl)acetic acid have been isolated and identified from a reaction between equivalent quantities of 1H-indazol-3-ol and ethyl chloroacetate in ethanol. The mechanism of their formation and, particularly, the ring enlargement of indazole to tetrahydroquinazoline is discussed. I.R. and N.M.R. spectra of these esters and of the acids obtained from them by alkaline hydrolysis are also described.

Acetates↗
PubMed1983

Investigation of granulocytopoietic kinetics by microdensitometric evaluation of primary granule naphthol-AS-D-chloroacetate esterase activity.

Using a scanning microscope photometer we determined quantitatively the enzymecytochemical reaction product for naphthol-AS-D-chloroacetate esterase in neutrophilic granulocytes and their precursors in man. Evaluation of neutrophilic cells from three healthy donors resulted in a logarithm-normal distribution. After subdivision of these cells in their morphologically defined maturational stages no statistically bimodal distribution was shown within the single cell groups. Myelocytes showed twice the amount of the polymorphonuclear neutrophil absorption values. The highest promyelocyte obsorptions were double the values of the myelocyte absorptions. The standard deviation of the absorbance obtained with promyelocytes (which encompass cells already producing granules up to cells reaching their maximal granule content) was significantly higher than the standard deviation of the myelocytes. As already known, primary granules are only synthesized at the promyelocyte stage and - according to the present knowledge - their chloracylesterase and peroxidase activities are not lost during further maturation. Consequently, our results indicate that only enzyme-rich, late promyelocytes undergo mitosis transforming into myelocytes. Correspondingly, their absorption value was halved. Since the absorbance from myelocytes to polymorphonuclears is again halved, myelocytes divide only once. Metamyelocyte absorptions in part correspond to that of myelocytes. This indicates that no distinction can be made between myelocytes with mitotic capacity and "true" if only the size and the nuclear shape are considered metamyelocytes which are not longer capable of undergoing mitosis.

Adult↗
PubMed1985

Naphthol AS D chloroacetate esterase-positive macrophages in the cortico-medullary zone of the normal rat thymus.

Naphthol AS D chloroacetate esterase (NASDCE)-positive macrophages are positioned in the cortico-medullary zone (CMZ) of the normal rat thymus. These cells contain the very strongly NASDCE-positive granules of varying size in the cytoplasm. An identical distribution within the thymic parenchyma and an identical morphological appearance is observed in CMZ macrophages after staining with aldehyde fuchsin. The incubation of thymic sections in 10% formalin at pH 7.0 for 48 h does not inhibit the activity of NASDCE in CMZ macrophages. The activity of nonspecific esterase is almost totally abolished by this treatment: only the single, largest globular inclusion within some of the cells remains weakly or moderately positive. The granular content of the CMZ macrophages does not stain metachromatically with toluidine blue and these cells are endogenous peroxidase-negative. NASDCE-positive thymic macrophages are easily distinguished from: a) NASDCE-positive mast-cells, which are confined to the capsular and septal connective tissue and contain densely packed metachromatic granules, and b) NASDCE-positive neutrophilic granulocytes, which have a specific morphological appearance and show very strong endogeneous peroxidatic activity.

Animals↗
PubMed1990

2-Chloroacetaldehyde and 2-chloroacetal are potent inhibitors of DNA synthesis in animal cells.

The effect of 2-chloroacetaldehyde, CAA, a metabolite of vinyl chloride and 2-chloroacetal, CAC, an ethyl diester of chloroacetaldehyde, on DNA synthesis in animal cells has been investigated. Both compounds drastically inhibited DNA synthesis at 10 to 20 microM. The inhibitory effect of the chemicals appears to be directly on DNA synthesis rather than on the uptake of thymidine or the formation of nucleotides. Residual DNA made in the presence of CAA had an average chain length of 300 nucleotides compared to a length of several thousand nucleotides in the absence of CAA. Synchronization experiments revealed that the inhibitory effect is reversible if 2-chloroacetaldehyde is removed within two hours but not after longer exposures.

Acetaldehyde↗
PubMed2004

Effects of superoxide dismutase and polyclonal tumor necrosis factor-alpha antibodies on chloroacetate-induced cellular death and superoxide anion production by J774.A1 macrophages.

Dichloroacetate (DCA) and trichloroacetate (TCA) are by-products that are formed during the process of water chlorination and have been previously shown to induce superoxide anion (SA) production and cellular death when added to J774.A1 macrophage cultures. In this study, the effects of superoxide dismutase (SOD) and polyclonal tumor necrosis factor-alpha (TNF-alpha) antibodies on DCA- and TCA-induced SA production and cellular death have been tested on the J774.A1 macrophage cultures. TCA and DCA were added to different cultures either alone, each at a concentration of 16 mM, or in combination with SOD (2-12 units/ml), or with TNF-alpha antibodies (10 and 25 units/ml). Cells were incubated for 48 h, after which cellular death/viability, lactate dehydrognase (LDH) leakage by the cells, and SA production by the cells were determined. While TCA and DCA caused significant cellular toxicity, indicated by reduction in cellular viability and increases in LDH leakage and SA production, SOD addition resulted in significant reduction of the effects induced by the compounds. On the other hand, addition of TNF-alpha antibodies to the DCA- and TCA-treated cultures resulted in significant reduction of DCA- but not TCA-induced cellular death and SA production by the cells. Although these results suggest a significant role for SA in DCA- and TCA-induced cellular death, they may also suggest two different mechanisms for the chloroacetate-induced SA production by the cells.

Acetates↗
PubMed2005

Electrochemical dechlorination of chloroacetic acids (CAAs) using hemoglobin-loaded carbon nanotube electrode.

Hemoglobin (Hb) was immobilized on carbon nanotube (CNT) electrode to catalyze the dechlorination of chloroacetic acids (CAAs), and the electrocatalytic behaviors of the Hb-loaded electrode for the dechlorination of trichloroacetic acid (TCAA) were studied by cyclic voltammetry and constant-potential electrolysis technique. An Hb-loaded packed-bed flow reactor was also constructed for bioelectrocatalytic dechloriantion of CAAs from drinking water. The results showed that the reduced heme of Hb immobilized on CNT electrode was easily regenerated, and Hb exhibited a stable and high activity for reductive dechlorination of CAAs with significant lowering of overpotential. TCAA could be reduced at -0.450 V (vs. saturated calomel electrode (SCE)) with catalysis of Hb-loaded electrode and its dechlorination was stepwise, following the pathway of TCAA-->dichloroacetic acid (DCAA)-->monochloroacetic acid (MCAA)-->acetic acid. It was also found that all CAAs, e.g., TCAA, DCAA and MCAA, could be dechlorinated completely at -0.450 V. The removal of 30.0 mM TCAA and DCAA is ca. 40% and 31%, respectively, with electrolysis for 100 min at -0.600 V (vs. SCE) using the Hb-loaded packed-bed flow reactor. The dechlorination activities of CAAs follow the decreasing order: TCAA>DCAA>MCAA, and the average current efficiency is over 90%.

Acetates↗
PubMed2005

Photocatalytic hydrogen generation in the presence of chloroacetic acids over Pt/TiO2.

In the presence of chloroacetic acids, the photocatalytic hydrogen evolution and decomposition of the pollutants over Pt/TiO2 have been investigated. The Pt/TiO2 was prepared by photodeposition. Monochloroacetic acid and dichloroacetic acid enhance photocatalytic hydrogen generation, whereas trichloroacetic acid does not. The photocatalytic oxidation of monochloroacetic acid and dichloroacetic acid mainly produces CO2, HCl and formaldehyde, whereas the photocatalytic oxidation of trichloroacetic acid mainly produces CO2 and HCl. The effect of the concentration of monochloroacetic acid and dichloroacetic acid on the hydrogen generation rate is consistent with a Langmuir-Hinshelwood kinetic model. A possible reaction mechanism was discussed.

Acetates↗
PubMed2006

Micronuclei induction and chromosomal aberrations in Rattus norvegicus by chloroacetic acid and chlorobenzene.

Chloroacetic acid (CAA) and chlorobenzene (CB) have been evaluated for in vivo mutagenic potential in Rattus norvegicus, employing the following criteria : (i) chromosomal aberrations (CAs) such as breaks, gaps, exchanges, rings, and multiple aberrations and (ii) micronuclei (MN) induction. Three sublethal doses, 0.008, 0.01, and 0.012 mg/g b. wt. of CAA and 0.75, 1.0, and 1.25 mg/g b. wt. of rat of CB were administered and the bone marrow cells evaluated in each of the three treated groups at 12, 24, and 48 h, respectively. Mean MN frequencies of 4.40+/-0.2 and 5.42+/-0.3, obtained respectively for CAA and CB. The higher induction of MN by CAA and CB was dose- and time-dependent. Most significant impact (P<0.05) for either of the compounds was observed at 24h post administration, when the recorded mean frequency of CAs was maximum for CAA (4.33+/-0.6) as well as for CB (4.66+/-0.5).

Acetates↗
PubMed2001

The fate and persistence of trifluoroacetic and chloroacetic acids in pond waters.

The environmental fate of trichloro-, dichloro-, and monochloroacetic acids, and trifluoroacetic acid was investigated using field aquatic microcosms and laboratory sediment-water systems. Trifluoroacetic acid was extremely persistent and showed no degradation during a one-year field study, though it appeared to undergo transient partitioning within an unknown pond phase as the temperature of the surroundings was reduced. Of the three chloroacetic acids, trichloro had the longest residence time (induction and decay) (approximately 40 d), dichloro the shortest (approximately 4 d), and monochloro an intermediate residence time (approximately 14 d). Laboratory studies suggest that the biodegradation of trichloro-, dichloro-, and monochloroacetic acids leads primarily to the formation of chloride and oxalic, glyoxalic, and glycolic acids, respectively.

Acetates↗
PubMed2000

Negative ion electrospray of bromo- and chloroacetic acids and an evaluation of exact mass measurements with a bench-top time-of-flight mass spectrometer

The negative ion electrospray mass spectra of six bromo- and chloroacetic acids were measured using two different electrospray interfaces and single quadrupole and bench-top time-of-flight mass spectrometers. With each acid at 50 microg/mL in aqueous methanol at pH 10, the anions observed included deprotonated molecules, adducts, and fragment ions. With each acid at 100 ng/mL in aqueous acetonitrile at pH 10, mainly deprotonated molecules are observed. The exact m/z measuring capability of the time-of-flight mass spectrometer was evaluated to assess the potential for the determination of the individual acids in mixtures without an on-line separation. Mean measurement errors were nearly always less than +/- 9 ppm and the majority were less than +/- 5 ppm. Potential interferences by substances having similar exact masses and the ability to form anions in aqueous solutions were evaluated. The estimated detection limits of the five regulated haloacetic acids in drinking water, without a sample preconcentration step, are in the range of 24-86 ng/mL, which is within about a factor of 10 of the levels required for routine monitoring of the acids. Actual drinking water samples were not analyzed pending the development of slightly more sensitive techniques and quantitative analytical procedures.

Journal Article↗
PubMed1982

Evidence for a close similarity in the catalytic sites of papain and ficin in near-neutral media despite differences in acidic and alkaline media. Kinetics of the reactions of papain and ficin with chloroacetate.

1. The pH-dependences of the second-order rate constants (k) for the alkylation by chloroacetate of the active-centre thiol groups of papain (EC 3.4.22.2) and ficin (EC 3.4.22.3) were determined over a wide range of pH at 25 degrees C at I 0.1. 2. The main feature of both pH-k profiles is a striking rate maximum at pH6 (characterizing parameters in both cases pKI approx. 3.5, pKII approx. 8.4 and pH-independent rate constant approximately kXH 2.5-3.0 M-1 . s-1). 3. The profile for the ficin reaction contains a plateau at high pH, with approximately kX 0.10 M-1 . s-1; if an analogous plateau exists in the papain reaction, approximately kX ix much lower, less than 0.02 M-1 . s-1. 4. Both enzymes appear to contain closely similar thiolate-imidazolium interactive systems at pH6, but differences in their behaviour in more-acidic media and in alkaline media suggest differences in interaction with the postulated carboxylate component of the putative catalytic triad.

Acetates↗
PubMed2005

Characterization of the metabolic interaction between trihalomethanes and chloroacetic acids using rat liver microsomes.

The aim of this study was to investigate the in vitro metabolism of trihalomethanes (THMs) in the presence of trichloroacetic acid (TCA), dichloracetic acid (DCA), monochloroacetic acid (MCA), and 4-methylpyrazole (4-MP) using liver microsomes from male Sprague-Dawley rats. Using the vial equilibration technique, initial experiments were carried out with starting concentrations of approximately 40 ppm THMs and 12-22 mM chloroacetic acids. The results indicated a mutual metabolic inhibition between THMs present as binary or quaternary mixtures. Although DCA and MCA had no influence on THMs, TCA produced a marked inhibition of the metabolism of all THMs: chloroform (CHCl3) (55%), bromodichloromethane (BDCM) (34%), dibromochloromethane (DBCM) (30%), and bromoform (TBM) (23%). The presence of 4-MP also reduced THM metabolism, the importance of which decreased in the following order: CHCl3 > BDCM > DBCM = TBM. In further vial equilibration experiments, using 9-140 ppm as starting concentrations of THMs, enzyme kinetic parameters (i.e., Michaelis constant, K(m), and maximum velocity, V(max)) were determined both in the absence and in the presence of TCA (12.2 mM). Results are consistent with a competitive inhibition between TCA and CHCl3, whereas the metabolic inhibition of BDCM and TMB by TCA was non-competitive. As for DBCM, results suggest a more complex pattern of inhibition. These results suggest that CYP2E1 is involved in the metabolism of THMs as well as in the metabolic interaction between THMs and TCA.

Acetates↗
PubMed1983

Microgranular acute promyelocytic leukemia--a case with multiple Auer rods demonstrable only after staining for chloroacetate esterase.

In the past several years there has been increasing recognition of the microgranular variant of acute promyelocytic leukemia (APL). This variant is easily mistaken for other types of acute non-lymphocytic leukemia. Its recognition is important because it carries the same high risk of disseminated intravascular coagulation as typical APL. An important clue to the correct diagnosis is the recognition of small numbers of characteristic cells containing multiple Auer rods. This report presents a case in which such Auer-body-containing cells were demonstrable in the marrow only after staining for chloroacetate esterase. They were not apparent with Wright's stain or Sudan black B. The case also highlights the occurrence of variant APL in children and adolescents.

Adolescent↗
PubMed1985

Chloroacetate esterase positivity in acute lymphoblastic leukemia.

Chloroacetate esterase (CAE) reactivity is associated with acute nonlymphocytic leukemia (ANLL) and, to the author's knowledge, has not been reported in acute lymphoblastic leukemia (ALL). The authors have identified a single patient whose blasts displayed CAE reactivity from a review of 400 newly diagnosed patients with ALL. The diagnosis of ALL in this case was based upon morphologic evaluation (FAB:L1), presence of terminal deoxynucleotidyl transferase (TdT), the absence of reactivity with myeloperoxidase, and the failure of leukemic blasts to mark with a panel of anti-myeloid monoclonal antibodies. Remission was induced promptly with standard ALL therapy. This case demonstrates that punctate CAE positivity rarely can occur in ALL, and, therefore, CAE is not entirely specific for ANLL. The authors conclude that CAE positivity should not be used as a sole criterion to diagnose ANLL in the absence of supporting morphologic, cytochemical, immunocytologic, or clinical information.

Bone Marrow↗