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Query: EC:3.4.15.1 (
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18,300
document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)
1,3-Dichloro-2-propanol
(1,3-
DCP
-OH, glycerol dichlorohydrin) is of great importance in many industrial processes and has been detected in foodstuffs, in particular in soup spices and instant soups. It has been shown to be carcinogenic, genotoxic and mutagenic. Its genotoxic mechanisms are, however, not yet entirely understood. We have investigated whether alcohol dehydrogenase (ADH) catalysed activation to the highly mutagenic and carcinogenic 1,3-dichloroacetone or formation of epichlorohydrin or other genotoxic compounds play a role for mutagenicity and genotoxicity. In our studies, no indications of ADH catalysed formation of 1,3-dichloropropane could be found, although we could demonstrate a clear activation by ADH in the case of 2-chloropropenol. Formation of allyl chloride could also be excluded. We found, however, clear evidence that epichlorohydrin formed chemically in the buffer and medium used in the test is responsible for genotoxicity. No indication was found that enzymatic formation of epichlorohydrin plays a role. Additional mutagenicity and genotoxicity studies with epichlorohydrin also confirmed the hypothesis that genotoxic effects of 1,3-
DCP
-OH depend on the chemical formation of epichlorohydrin.
...
PMID:Genotoxicity of 1,3-dichloro-2-propanol in the SOS chromotest and in the Ames test. Elucidation of the genotoxic mechanism. 191 79
The degradation of low concentrations of
1,3-dichloro-2-propanol
(1,3-
DCP
) and related halohydrins by whole cells and cell-free extracts of soil bacteria has been investigated. Three bacteria (strains A1, A2, A4), isolated from the same soil sample, were distinguished on the basis of cell morphology, growth kinetics and haloalcohol dehalogenase profiles. Strain A1, probably an Agrobacterium sp., dehalogenated 1,3-
DCP
with the highest specific activity (0.33 U mg protein-1) and also had the highest affinity for 1,3-
DCP
(Km, 0.1 mM). Non-growing cells of this bacterium dehalogenated low concentrations of 1,3-
DCP
with a first-order rate constant (kl) of 1.13 h-1. The presence of a non-dehalogenating bacterium, strain G1 (tentatively identified as Pseudomonas mesophilius), did not enhance the dehalogenation rate of low 1,3-
DCP
concentrations. However, the mixed-species consortium of strains A1 and G1 had greater stability than the mono-species culture at
DCP
concentrations above 1.0 gl-1.
...
PMID:Biodehalogenation of low concentrations of 1,3-dichloropropanol by mono- and mixed cultures of bacteria. 900 96
Arthrobacter erithii H10a possesses two enzymes capable of catalyzing the dehalogenation of vicinal halohydrins which have been designated as dehalogenases DehA and DehC. The DehA dehalogenase demonstrated greater activity toward
1,3-dichloro-2-propanol
(1,3-
DCP
) while the DehC dehalogenase showed higher activity toward 3-chloro-1,2-propanediol (3-CPD) and brominated alcohols. The DehA dehalogenase was composed of two non-identical subunits (relative molecular mass of 31.5 and 34 kDa) which probably associate with other proteins to form a large catalytically active protein of 200 kDa. The two subunits were purified and the amino acid sequence of their tryptic digests determined. The DehA enzyme catalyzed the conversion of vicinal halohydrins to epoxides and the reverse reaction in the presence of an excess of halogen. This enzyme had maximum activity at 50 degrees C and a broad pH optimum over the range 8.5-10.5. The apparent K(m) and Vmax values for dehalogenation of 1,3-
DCP
and 3-CPD were 0.105 mM and 223 mumol min-1 mg-1; and 2.366 mM and 1.742 mumol min-1 mg-1, respectively. The enzyme was inhibited by 2-chloroacetic acid (MCA) and 2,2-dichloroacetic acid (DCA). The inhibition pattern suggested a mixed type inhibition which was predominantly uncompetitive. Amino acid modification experiments demonstrated that one or more cysteine and arginine residues are likely to be involved in catalysis or play an important role in the maintenance of the enzyme structure. The characteristics of the DehA enzyme are compared to those of previously reported haloalcohol dehalogenases and discussed in terms of diversity of this type of dehalogenase.
...
PMID:Biochemical characterization of a haloalcohol dehalogenase from Arthrobacter erithii H10a. 962 48
The influence of fasting (18 hours) on the hepatotoxicity of
1,3-dichloro-2-propanol
(1,3-
DCP
) and on various hepatic parameters has been assessed in the rat. Fasting produced an enhancement of the hepatotoxicity which was associated with alterations in a variety of hepatic parameters when measured relative to protein content, most notably glutathione (GSH) levels (decrease) and CYP2E1-mediated enzyme activity (increase), two parameters previously identified as being important determinants to the toxicity. Fasting also decreased the liver weight normalized to body weight. When this was taken into account, total liver CYP2E1-mediated enzyme activity was not significantly altered whereas the total liver GSH level was markedly reduced following fasting. These results imply that the reduction in hepatic GSH is the principal determinant of the enhanced susceptibility to 1,3-
DCP
hepatotoxicity following fasting.
...
PMID:Depression of glutathione content, elevation of CYP2E1-dependent activation, and the principal determinant of the fasting-mediated enhancement of 1,3-dichloro-2-propanol hepatotoxicity in the rat. 1041 53
1,3-Dichloro-2-propanol
(1,3-
DCP
) is a chlorinated compound used in the fabrication of industrial products such as hard resins, celluloid or paints. It has also been detected in instant soups and soy sauce. 1,3-
DCP
has been associated with major necrosis of the liver in humans [Chem.-Bio. Interact. 80 (1991) 73]. In humans and laboratory animals, 1,3-
DCP
is metabolised to dichloroacetone (1,3-DCA) by cytochromes P450 2E1 and 1A2 [J. University Occup. Environ. Health 14 (1992) 13]. 1,3-DCA is a hepatotoxin. We suggest that 1,3-DCA could be embryotoxic at doses that do not cause adverse maternal hepatic damage. To investigate the embryotoxic effects of 1,3-DCA, we have adapted a micromass culture method from Atterwill and colleagues [1992. A tiered system for in vitro neurotoxicity testing. In: Zbinden, G. (Ed.), The Brain in Bits and Pieces. Verlag M.T.C., Vollikon, pp. 89-91], using chick midbrain cells and from Wiger et al. [Pharmacol. Toxicol. 62 (1988) 32] using chick mesenchymal cells. The basis of the micromass system is that embryotoxins in vitro are likely to affect development and differentiation of disaggregated neuronal and limb bud micromass cultures. The endpoints chosen for the midbrain assay are resazurin reduction (viability), total protein content (cell number), morphological quantification of neuronal cultures (neuronal projection number) and of limb bud cultures (cartilage nodule number). Preliminary results using chick whole embryo cultures indicated that 1,3-DCA had an inhibitory effect on whole chick embryo development. We also found that embryonic derived cells were sensitive to 1,3-DCA but not 1,3-
DCP
at concentrations above 1 microM, suggesting a potential teratogenic effect of 1,3-DCA. The exposure to 1,3-
DCP
is not limited to industrial settings, and hence a better knowledge of its effects and tissue specific actions on embryonic-derived cells would be beneficial.
...
PMID:The relative embryotoxicity of 1,3-dichloro-2-propanol on primary chick embryonic cells. 1211 Feb 83
Microbial cultures able to degrade xenobiotic compounds are the key element for biological treatment of waste effluents and are obtained from enrichment processes. In this study, two common enrichment methods, suspension batch and immobilized continuous, were compared. The main selection factor was the presence of
1,3-dichloro-2-propanol
(1,3-
DCP
) as the single carbon source. Both methods have successfully enriched microbial consortia able to degrade 1,3-
DCP
. When tested in batch culture, the degradation rates of 1,3-
DCP
by the two consortia were different, with the consortia obtained by batch enrichment presenting slightly higher rates. A preliminary morphological and biochemical analysis of the predominant colonial types present in each degrading consortia revealed the presence of different constituting strains. Three bacterial isolates capable of degrading 1,3-
DCP
as single strains were obtained from the batch enrichments. These strains were classified by 16S rRNA analysis as belonging to the Rhizobiaceae group. Degradation rates of 1,3-
DCP
were lower when single species were used, reaching 45 mg 1(-1) d(-1), as compared to 74 mg 1(-1) d(-1) of the consortia enriched on the batch method. Mutualistic interactions may explain the better performance of the enriched consortia.
...
PMID:Enrichment of microbial cultures able to degrade 1,3-dichloro-2-propanol: a comparison between batch and continuous methods. 1249 18
A survey of soy sauces and related products available in the USA was conducted to determine the levels of 3-monochloropropane-1,2-diol (3-MCPD) and
1,3-dichloro-2-propanol
(1,3-
DCP
) in these products. Fifty-five retail samples were purchased and analysed for 3-MCPD. 3-MCPD determinations were made according to a gas chromatography/mass spectrometry method validated by a collaborative trial. Eighty-five per cent of the samples analysed contained greater than the detection limit of 0.005 ppm (microg g(-1)) for 3-MCPD. Thirty-three per cent contained greater than 1 ppm; the highest level was 876 ppm 3-MCPD. Thirty-nine of the samples analysed for 3-MCPD also were analysed for 1,3-
DCP
by using a modified method developed and validated in-house. Fifty-six per cent of the samples analysed for 1,3-
DCP
contained greater than the detection limit of 0.055 ppb (ng g(-1)) for 1,3-
DCP
; the highest level was 9.8 ppm 1,3-
DCP
. Products manufactured in Asia contained the highest chloropropanol levels.
...
PMID:Survey of chloropropanols in soy sauces and related products. 1459 75
A rapid analytical method for sensitive determination of
1,3-dichloro-2-propanol
(1,3-
DCP
) in river water has been developed. 1,3-
DCP
is extracted from water with ethyl acetate. After filtration through sodium sulfate the ethyl acetate phase is analyzed by gas chromatography-mass spectrometry. The method uses 1,3-
DCP
-d5 as internal standard. Different extraction solvents, concentrations of ammonium sulfate in the water samples, and the effect of humic acid were tested and their influence on the recovery of
DCP
has been evaluated. The method quantification limit was 0.1 microg L(-1). For spiked water samples (0-5.2 microg L(-1), n=21) a repeatability coefficient of variation of 5.4% was obtained. The average recovery rate of 1,3-
DCP
was 105+/-3% (n=21). Stability tests, which were carried out with Danube river water, led to an estimated 1,3-
DCP
degradation rate of 0.008+/-0.0008 day(-1) at 6 degrees C.
...
PMID:A rapid and sensitive GC-MS method for determination of 1,3-dichloro-2-propanol in water. 1585 97
The removal of
1,3-dichloro-2-propanol
(1,3-
DCP
), 3-chloro-1,2-propanediol (3-CPD) and their mixtures at concentrations up to 1,000 mg . L(-1) by the whole cell system of Pseudomonas putida DSM 437 was investigated. The 1,3-
DCP
removal rates ranged from 2.36 to 10.55 mg . L(-1) . h(-1); 3-CPD exhibited approximately two times higher removal rates compared to 1,3-
DCP
for all concentrations tested. Removal of 1,3-
DCP
and 3-CPD followed first-order kinetics with rate constants of 0.0109 h(-1) and 0.0206 h(-1), respectively. When the whole cell system of P. putida DSM 437 was applied to mixtures of the two halohdrins, complete removal of 1,3-
DCP
was achieved at 144 h while removal of 3-CPD was completed at times ranging from 72 to 144 h. Time to achieve 50% removal of both halohydrins depends on the initial concentration of each in the mixture. For 1,3-
DCP
, it ranged from 40.55 h at 200 mg . L(-1) to 53.28 h at 500 mg . L(-1) while the respected values for 3-CPD were 33.39 and 68.91 h.
...
PMID:Removal of 1,3-dichloro2-propanol and 3-chloro1,2-propanediol by the whole cell system of pseudomonas putida DSM 437. 1648 65
The photocatalytic oxidation of
1,3-dichloro-2-propanol
(1,3-
DCP
) was studied by following the target compound degradation, the total organic carbon removal rate and by identifying the oxidation products. The reaction was performed in a batch recycle reactor, at room temperature, using UV radiation, H2O2 as oxidant, and immobilized TiO2 as catalyst. 1,3-Dichloro-2-propanone, chloroacetyl-chloride, chloroacetic acid, formic and acetic acid were detected as reaction intermediates and a possible pathway for the oxidation of
1,3-dichloro-2-propanol
is proposed. The effect of the oxidative agent's initial concentration was investigated and it was established that higher concentrations of H2O2 slow down the reaction rate. The investigation of the effect of the 1,3-
DCP
initial concentration showed no influence on the degradation process. The carbon and chloride ion mass balance calculations confirmed the fact that chlorinated intermediates are formed and that they degrade with a lower rate than 1,3-
DCP
.
...
PMID:Photocatalytical degradation of 1,3-dichloro-2-propanol aqueous solutions by using an immobilized TiO2 photoreactor. 1670 12
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