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At least 73 records · Page 4Linked to original sources
PubMed1992

Chloroacetates of 2- and 3-demethylthiocolchicine: specific covalent interactions with tubulin with preferential labeling of the beta-subunit.

We synthesized two chemically reactive A ring modified analogs of colchicine, 2-chloroacetyl-2-demethylthiocolchicine (2-CTC) and 3-chloroacetyl-3-demethylthiocolchicine (3-CTC). Both are similar to colchicine as inhibitors of tubulin polymerization and act as competitive inhibitors of colchicine binding (apparent Ki values, 3 microM). [14C]-labeled 2-CTC and 3-CTC bound to tubulin at 37 degrees C but not at 0 degree C, and bound drug formed covalent bond(s) with tubulin. The binding and covalent reactions were inhibited by podophyllotoxin. About 60% of the bound 3-CTC rapidly formed a covalent bond with tubulin. With 2-CTC the covalent reaction was slower than the binding reaction, and only one-third of the bound 2-CTC reacted covalently with tubulin. The ratio of radiolabel in beta-tubulin to that in alpha-tubulin was about 4:1 with both 2-CTC and 3-CTC.

Binding, Competitive↗
PubMed1989

Species and strain sensitivity to the induction of peroxisome proliferation by chloroacetic acids.

B6C3F1 mice and Sprague-Dawley rats were provided drinking water containing 6-31 mM (1-5 g/liter) trichloroacetic acid (TCA), 8-39 mM (1-5 g/liter) dichloroacetic acid (DCA), or 11-32 mM (1-3 g/liter) monochloroacetic acid (MCA) for 14 days. TCA and DCA, but not MCA, increased the mouse relative liver weight in a dose-dependent manner. Rat liver weights were not altered by TCA or DCA treatment, but were depressed by MCA. Hepatic peroxisome proliferation was demonstrated by (1) increased palmitoyl-CoA oxidase and carnitine acetyl transferase activities, (2) appearance of a peroxisome proliferation-associated protein, and (3) morphometric analysis of electron micrographs. Mouse peroxisome proliferation was enhanced in a dose-dependent manner by both TCA and DCA, but only the high DCA concentration (39 mM) increased rat liver peroxisome proliferation. MCA was ineffective in both species. Three other mouse strains (Swiss-Webster, C3H, and C57BL/6) and two strains of rat (F344 and Osborne-Mendel) were examined for sensitivity to TCA. TCA (12 and 31 mM) effectively enhanced peroxisome proliferation in all mouse strains, especially the C57BL/6. A more modest enhancement in the Osborne-Mendel (288%) and F344 rat (167%) was seen. Dosing F344 rats with 200 mg/kg TCA in water or corn oil for 10 days increased peroxisome proliferation 179 and 278%, respectively, above the vehicle controls. These studies demonstrate that the mouse is more sensitive than the rat with respect to the enhancement of liver peroxisome proliferation by TCA and DCA and suggest that if peroxisome proliferation is critical for the induction of hepatic cancer by TCA and DCA, then the rat should be less sensitive or refractory to tumor induction.

Acetates↗
PubMed2006

Epoxysilane rearrangement induced by a carbanion generated by conjugate addition of enolates of chloroacetate and alpha-chloroacetamides: formation of functionalized cyclopropane derivatives.

[reaction: see text] Reaction of an enoate bearing an epoxysilane moiety at the alpha-position with lithium enolate of 2-chloroacetamide afforded highly functionalized cyclopropane derivatives via a tandem process that involves Michael addition, ring opening of the epoxide, Brook rearrangement, and intramolecular alkylation.

Journal Article↗
PubMed2003

Chloroacetic acids in European soils and vegetation.

Trichloroacetic acid (TCA) and dichloroacetic acid (DCA) are possible minor atmospheric degradation products of perchloroethylene and trichloroethylene, respectively. These acids may be wet- or dry-deposited from the atmosphere to land surfaces and hence possibly affect plant growth. However, the existing database on TCA levels in soil is limited to a few studies carried out in the late 1980's and the early to mid-1990's and it was concluded that there is a need for further measurements of concentrations of TCA and DCA in soils. In this study soil samples from 10 locations in 5 European countries, as well as vegetation samples, and a limited number of rainwater and air samples were collected and analysed for DCA and TCA to determine the concentrations of these compounds. An isotope dilution method using GC-MS was used for the determination of these acids in the samples. The method was briefly validated and the performance characteristics are presented. The results of the analysis of the soil samples show that the DCA and TCA concentrations in soil from different sites in Europe are more or less comparable, with the exception of Germany, especially Freudenstadt, where significantly higher TCA concentrations (up to 12 microg kg(-1) dw) were found. The average DCA and TCA concentrations in soil in this study were 0.25 +/- 0.12 and 0.64 +/- 1.40 microg kg(-1) dw, respectively. Generally, the concentration in soils from forest areas are about twice those from open-land areas. The DCA and TCA concentrations in vegetation samples ranged from 2.1 to 73 microg kg(-1) dw for DCA and from 4.7 to 17 microg kg(-1) dw for TCA. Thus, the concentrations in vegetation samples are 10-20 times higher than the soil concentrations. DCA and TCA concentrations in wet deposition samples and air samples collected in The Netherlands were 0.14 and 0.15 microg l(-1) for wet deposition samples and <0.5 and 0.7 ng m(-3) for air samples respectively. For these samples taken in The Netherlands, the estimated values for soil and air concentrations calculated from the wet deposition concentrations are in agreement with the concentrations measured in this study.

Acetates↗