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PubMed2001

Identification of UV photoproducts and hydrolysis products of butachlor by mass spectrometry.

The photoproducts and hydrolysis products of butachlor in water were identified by gas chromatography/mass spectrometry. When exposed to UV light, butachlor in aqueous solution was rapidly degraded, giving at least 11 photoproducts as a result of dechlorination with subsequent hydroxylation or cyclization processes. The chemical structures of nine degradation compounds were identified on the basis of mass spectrum interpretation and literature data. Major photoproducts are identified as 8-ethyl-1-butoxymethyl-4-methyl-2-oxo-1,2,3,4-tetrahydro-quinoline, 2-hydroxy-2',6'-diethyl-N-(butoxymethyl) acetanilide, and a compound related to butachlor. Minor photoproducts are identified as 2,6-diethylaniline; 1-acetyl-7-ethylindole; N-(2,6-diethylphenyl)-N-(butoxymethyl)acetamide; 2-oxo-N-(2,6-diethyl-phenyl)-N-(butoxymethyl)acetamide; 1-hydroxyacetyl-2-butoxyl-3-methyl-7-ethylindole; 1-acetyl-2-butoxyl-3-methyl-7-ethylindole; and two compounds with the chemical structure unknown. The half-lives of butachlor UV photolysis were 7.54, 10.56, and 12.22 min in deionized water, river water, and paddy water, respectively. The half-lives of butachlor hydrolysis at pH 4, 7, and 10 were 630, 1155, and 1155 days at 25 +/- 1 degrees C, respectively. A hydrolysis product at pH 4 was identified by GC/MS to be 2-hydroxy-2',6'-diethyl-N-(butoxymethyl) acetanilide.

Acetanilides↗
PubMed1974

Hepatic drug hydroxylation and lipid peroxidation in riboflavin-deficient rats.

The effect of riboflavin deficiency and phenobarbital pretreatment on drug hydroxylation and lipid peroxidation was investigated. A significant decrease in aniline and acetanilide hydroxylation as well as NADPH-linked and ascorbate-induced lipid peroxidation was observed during 4- and 7-week riboflavin deficiency in both adult male and adult female rats. The drug-hydroxylation and lipid-peroxidation activities were further lowered with the increase in riboflavin deficiency. The phenobarbital pretreatment induced aniline and acetanilide hydroxylase activity even in riboflavin-deficient animals. Drug hydroxylation inhibits lipid peroxidation in both deficient and normal rats. The administration of riboflavin was followed by a significant increase in drug hydroxylation and lipid peroxidation.

Acetanilides↗
PubMed1998

Effects of the agrochemicals butachlor, pretilachlor and isoprothiolane on rat liver xenobiotic-metabolizing enzymes.

1. The herbicides butachlor (2-chloro-2',6',diethyl-N-[buthoxymethyl] acetanilide) and pretilachlor (2-chloro-2',6'-diethyl-N-[2-propoxyethyl] acetanilide) are widely used in Asia, South America, Europe and Africa. Isoprothiolane (diisopropyl-1,3-dithiolan-2-ylidenemalonate) is used as a fungicide and an insecticide in rice paddies. We administered these agrochemicals to the male rat and examined their effects on cytochrome P450 (P450), glutathione S-transferase (GST), UDP-glucuronosyltransferase (UDPGT), and NAD(P)H-quinone oxidoreductase 1 (NQO1)-related metabolism in the liver. 2. Administration of isoprothiolane, butachlor or pretilachlor to rat induced hepatic P4502B subfamily-dependent enzyme activities (pentoxyresorufin O-depentylation and testosterone 16 beta-hydroxylation) up to 271-413% of control, which coincided with the increase in expression levels of the P4502B apoprotein. 3. Activities of GST toward 1-chloro-2,4-nitrobenzene and 3,4-dichloronitrobenzene were slightly induced (127-133% of control) in the liver of the rat treated with these pesticides. On the other hand, marked elevations of UDPGT activities toward p-nitrophenol (164-281% of control) were observed. NQO1-related metabolism (menadione reductase activity) was also induced (123-176% of control) in the liver of rat treated with these agrochemicals. 4. These results indicate that some of the agrochemicals currently in use are capable of inducing phase I and II xenobiotic-metabolizing enzyme activities in an isozyme selective manner. The induction of these activities may disrupt normal physiologic functions related to these enzymes in exposed animals.

Acetanilides↗
PubMed1980

Multiple forms of cytochrome P-450 purified from liver microsomes of phenobarbital- and 3-methylcholanthrene-pretreated rabbits. II. Spectral properties.

The spectral properties of multiple forms of cytochrome P-450 purified or partially purified from liver microsomes of phenobarbital (PB)- and 3-methylcholanthrene (MC)-treated rabbits have been studied. Both optical absorption and EPR studies have shown that the oxidized forms of P-450(1), P-450(2) (from PB-treated animals), and P-450(3) (from MC-treated animals) are in the low spin state, having a Soret absorption peak at 417-418 nm. Oxidized P-448(1) (from both PB- and MC-treated animals), on the other hand, shows a Soret peak at 393 nm and a weak band at 646 nm. This and EPR evidence indicate that P-448(1) contains heme which is predominantly in the high spin state, though EPR studies at low temperature indicate the presence of a small amount of low spin ferric heme. The presence of tightly bound MC in P-448(1) purified from MM-treated animals is reflected by characteristic absorption peaks in the ultraviolet region, but this does not affect the absorption spectra in the Soret and visible regions. Emulgen 913, a nonionic detergent, causes the conversion of oxidized P-448(1) from the high to the low spin state, as evidenced by optical absorption and EPR results; bound MC inhibits this conversion in a noncompetitive way. Binding of ethyl isocyanide to reduced P-450(1) and P-448(1) results in the appearance of two Soret peaks in the 430 and 455 nm regions, the relative intensities of which are dependent on pH. At any pH the 455 nm peak of P-448(1) is always higher than that of P-450(1). Benzphetamine and aniline, added to oxidized P-450(1), cause Type I and Type II spectral changes, respectively, but the magnitudes of the changes are small in both cases. The Soret peak of oxidized P-448(1) at 393 nm is completely shifted to 420 nm on addition of aniline, resulting in a reverse Type I spectral change; acetanilide causes the conversion of the Soret peak to the low spin state to only a slight extent. The conversions caused by aniline and acetanilide are both inhibited by the presence of tightly bound MC. On the basis of these and other observations, the spin state of these P-450's are discussed.

Acetanilides↗
PubMed1986

Monooxygenase activity of Saccharomyces cerevisiae cells transformed with expression plasmids carrying rat cytochrome P-450MC cDNA.

The recombinant plasmids pAMC1 and pJMC1 were constructed; the former contained the cytochrome P-450MC (P-450MC) cDNA expression unit consisting of yeast alcohol dehydrogenase I (ADH) promoter, rat P-450MC cDNA and ADH terminator, and the Leu 2 marker gene, and the latter contained the same expression unit and the leu 2-d gene. Saccharomyces cerevisiae AH22 cells transformed with each of the recombinant plasmids were examined for plasmid copy number, P-450MC mRNA level, P-450MC content, and monooxygenase activity. The S. cerevisiae AH22/pJMC1 cells contained about 2-fold higher levels of the plasmid, P-450MC mRNA, and P-450MC than the AH22/pAMC1 cells. Monooxygenase activity towards 7-ethoxycoumarin and acetanilide of the AH22/pJMC1 cells was 1.7-fold and 1.5-fold higher than that of the AH22/pAMC1 cells, respectively, whereas the activity of the AH22/pAMC1 cells towards 7-ethoxycoumarin and acetanilide was more than 1,000-fold 10-fold higher than that of the control AH22/pAAH5 cells which contain no P-450MC cDNA, respectively. Therefore, it is likely that monooxygenase activity of the AH22 cells carrying rat P-450MC cDNA was approximately proportional to the expression level of P-450MC cDNA.

Acetanilides↗
PubMed1978

Assessment of the utility of gallbladder imaging with 99mTc-IDA.

Cholescintigraphy was performed in 113 patients of whom 38 had normal gallbladders, 37 had acute cholecystitis and 38 had chronic cholecystitis. The radiopharmaceuticals used in the study were either 99mTc-dimethyl acetanilide iminodiacetic acid or 99mTc-paraisopropyl acetanilide iminodiacetic acid, both of which performed equally well. All patients with non-visualized gallbladders had cholecystitis, but visualization did not exclude disease. The rapidity of obtaining the results (within one hour), the complete absence of untoward reactions to the radiopharmaceuticals, the much lower frequency of subtle or indeterminate results, the ability to render useful information in the presence of moderate jaundice and the lack of interference from overlying intestinal contents establishes these radionuclide agents as superior to both radiographic oral and intravenous cholangiography in the investigation of the acute abdomen.

Acetanilides↗
PubMed2000

Propachlor removal by Pseudomonas strain GCH1 in an immobilized-cell system.

A bacterial strain capable of growing on propachlor (2-chloro-N-isopropylacetanilide) was isolated from soil by using enrichment and isolation techniques. The strain isolated, designated GCH1, was classified as a member of the genus Pseudomonas. Washed-cell suspensions of strain GCH1 accumulated N-isopropylacetanilide, acetanilide, acetamide, and catechol. Pseudomonas strain GCH1 grew on propachlor with a generation time of 4.2 h and a rate of substrate utilization of 1.75 +/- 0.15 micromol h(-1). Gene expression did not require induction but was subject to catabolite expression. Acetanilide was a growth substrate with a yield of 0.56 +/- 0.02 mg of protein micromol(-1). GCH1 strain cells were immobilized by adsorption onto a ceramic support and were used as biocatalysts in an immobilized cell system. Propachlor elimination reached 98%, with a retention time of 3 h and an initial organic load of 0.5 mM propachlor. The viability of immobilized cells increased 34-fold after 120 days of bioreactor operation.

Acetamides↗
PubMed1977

Hepatic drug acetylation and oxidation: effects of aging in man.

The half lives of acetanilide and isoniazid ("model" substrates for oxidation and acetylation respectively) were measured in populations of young (aged 20-35 years) and elderly (aged over 65 years) people. Whereas acetanilide half lives were significantly longer in the elderly, isoniazid half lives were distributed similarly in both populations. The results suggest that liver function does not decline uniformly with age and that heterozygotes for acetylation do not possess survival advantages during their middle years of life.

Acetanilides↗
PubMed1976

Comparative metabolic studies of phenacetin and structurally-related compounds in the rat.

1. A comparative study of the metabolism of [acetyl-14C]phenacetin, [acetyl-14C]methacetin, [acetyl-14C]paracetamol and [acetyl=14C]acetanilide in the rat is reported. 2. The extent of N-deacetylation, evidenced by the measurement of respired 14CO2, varied, being greatest with acetanilide (25-31%) and least with paracetamol (6%). 3. The major urinary metabolites in each case were N-acetyl-p-aminophenyl sulphate and N-acetyl-p-aminophenyl glucuronide; the relative proportions varied with the sex of the animals and as a result of extended dosage. 4. The metabolism of [ethyl-14C]phenacetin and [ethyl-14C]phenetidine was investigated and the extent of O-dealkylation determined by measurement of respired 14CO2. 5. The metabolic pathways of some related glycolanilides and oxanilic acids included N-deacylation, and in the glycolanilides, oxidation of the glycollic group.

Acetaminophen↗
PubMed1996

Phytotoxic effects of benzimidazole fungicides on bedding plants.

Benzimidazoles are effective and widely used fungicides, but they may be phytotoxic. We studied the effects of a single drench application of six benzimidazoles and one acetanilide fungicide on photosynthetic gas exchange, growth, development, and nutrient levels of four species of bedding plants in twenty growth-chamber and four greenhouse studies. Daily carbon gain and carbon-use efficiency were calculated from continuous crop gas-exchange measurements in the growth chambers. The maximum labeled rate of Benlate DF caused a 7- to 10-day decrease in net photosynthesis and daily carbon gain in transplants of all species. It also caused pronounced interveinal chlorosis and a 2- to 3-day delay in flowering. Growth of Benlate DF-treated plants was reduced more at high (90%) than at low (60% to 80%) relative humidity. Benlate DF had severe effects on 2-week-old petunia (Petunia xhybrida) seedlings in plug flats, reducing photosynthesis 25% to 57%. Cleary's 3336 WP decreased photosynthesis in some trials. Benlate DF reduced photosynthesis within 24 hours, but 3336 WP effects did not become apparent until 1 week after the treatment. This suggests different modes of inhibition. 3336 WP also caused leaf-tip and marginal chlorosis in impatiens (Impatiens wallerana). Mertect 340-F was extremely phytotoxic but is not labeled for drench applications (it was included because of its chemical similarity to other benzimidazoles). The only benzimidazole fungicide that did not reduce photosynthesis was Derosal, but it caused slight interveinal chlorosis in some studies with petunia. Benlate DF and Derosal decreased leaf Ca levels. Subdue (or metalaxyl), an acetanilide fungicide, did not affect photosynthesis or cause any visual symptoms. Our results indicate that some benzimidazole fungicides can cause growth reductions and visual damage in bedding plants.

Acetanilides↗
PubMed1990

Effect of mancozeb on hydrolytic metabolism of xenobiotics.

The present investigation reports the effect of chronic oral administration of mancozeb, a fungicide, on hepatic microsomal carboxylesterases/amidases or B-esterases responsible for hydrolytic metabolism of aspirin (acetylsalicylic acid or ASA) at pH 5.5 and 7.4, 2-acetylaminofluorene (AAF), acetanilide and p-nitrophenylacetate (NPA) and cholinesterase in rat. Oral administration of mancozeb (250 mg/kg/day) for 30 days caused significant stimulation of ASA esterase I (pH 5.5), ASA esterase II (pH 7.4), AAF N-deacetylase and acetanilide N-deacetylase in liver. However, the activities of NPA esterase and cholinesterase remained unaffected. Evaluation of induction kinetics demonstrated that the pattern and magnitude of responses of these microsomal hydrolases to mancozeb treatment for 7 days were comparable to those obtained after treatment for 30 days. The activities of hydrolases were not altered in animals killed 4 hr after an oral dose of mancozeb. Mancozeb did not affect these hydrolases in vitro.

2-Acetylaminofluorene↗
PubMed1977

Resolution of two forms of cytochrome P-450 from liver microsomes of rabbit treated with 2,3,7,8-tetrachlorodibenzo-p-dioxin.

Two forms of cytochrome P-450 with different substrate specificities were isolated from liver microsomes of rabbits treated with 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD). A specific antibody was produced toward the major form of the cytochrome. The antibody inhibits microsomal acetanilide hydroxylation (80%). It does not cross-react with the minor fraction of the cytochrome or inhibit the hydroxylation of 3,4-benzpyrene or coumarin, the N-demethylation of aminopyrine or the O-deethylation of 7-ethoxycoumarin catalyzed by rabbit liver microsomes. The major form has an estimated Mr = 54,000 and displays an n-octylamine difference spectrum with an absorption maximum at 426 nm and a minimum at 391 nm. When reconstituted, this cytochrome catalyzes acetanilide hydroxylation at a higher rate than microsomes or the minor fraction. The n-octylamine difference spectrum of the minor fraction displays an absorption maximum at 431 nm and a minimum at 410 nm. When reconstituted, this fraction catalyzes the hydroxylation of 3,4-benzpyrene and the O-deethylation of 7-ethoxycoumarin. The two cytochromes appear to be distinct entities and function in different catalytic pathways.

Acetanilides↗
PubMed1982

A series of inhibitors of azo dye hepatocarcinogenesis partially reverse the azo dye-induced decrease in liver RNA/DNA ratio.

The DNA and RNA content and the mitotic index were determined in the livers of rats pair-fed for 10 days on a control diet, and diets containing 0.06% 3'-methyl-4-dimethylaminoazobenzene (3'MeDAB), either alone or in combination with the inhibitors of azo dye carcinogenesis acetanilide (0.08%), p-hydroxypropiophenone (PHP, 1%), urea (5%), dehydroacetic acid (DHAA, 0.25%), butylated hydroxytoluene (BHT, 0.3%) and 3-methylcholanthrene (3MC, 0.067%). The liver RNA/DNA ratio was increased in rats fed the 3'MeDAB diet following ingestion of each of the inhibitor plus carcinogen-containing diets. The increases were significant except in the instance of urea. The increase was mainly due to increased RNA content in rats fed 3'MeDAB plus acetanilide, DHAA, BHT and 3MC when compared with rats fed 3'MeDAB alone. In rats fed PHP and 3'MeDAB, an increase in total liver DNA that was noted in rats fed 3'MeDAB alone did not take place, while total liver RNA content was similar in both groups; the RNA/DNA ratio was therefore greater in rats protected from 3'MeDAB carcinogenesis by PHP. The results are discussed in relationship to the effects of carcinogens on RNA forming genes and the role of the nucleolus in cell differentiation.

Acetanilides↗
PubMed1984

Gonadal hormone-induced changes in hepatic microsomal carboxylesterase in rats.

Hepatic microsomal carboxylesterase (E.C. 3.1.1.1) from rat liver microsomes showed a different capacity for the hydrolysis of various substrates. In castrated male rats, the enzyme activities towards p-nitrophenylacetate and malathion were decreased. When testosterone propionate was administered to castrated male rats, the activities of p-nitrophenylacetate and malathion hydrolases were reversely increased. However, in ovariectomized female rats, the carboxylesterase activities showed substrate-dependent changes, i.e., increase in p-nitrophenylacetate and malathion hydrolases and decrease in acetanilide and isocarboxazid hydrolases. When estradiol benzoate was administered to ovariectomized female rats, the activities of p-nitrophenyl-acetate and malathion hydrolases were decreased; and acetanilide and isocarboxazid hydrolases were increased. These results suggest that hepatic microsomal carboxylesterases may be, at least in part, regulated by gonadal hormones which exert different effects on the several isozymes of carboxylesterases.

Acetanilides↗
PubMed1976

Hepatic drug metabolism and lipid peroxidation in thiamine deficient rats.

In vitro metabolism of aminopyrene, ethylmorphine (Type I substrates), N-methylaniline and acetanilide (Type II substrates) in liver microsomal fraction from thiamine deficient male and female rats was studied. No significant change in microsomal protein content was noticed during the period of thiamine deficiency. However, a significant increase in the in vitro oxidation of aminopyrene, ethylmorphine, N-methylaniline and hydroxylation of acetanilide was observed. The NADPH linked and ascorbate induced lipid peroxidation was also increased during thiamine deficiency. The levels of NADPH cytochrome c-reductase, cytochrome b5 and heme were noticeably increased in thiamine deficient animals as compared to normal rats. Phenobarbital treatment induced the activities of all drug enzymes and inhibited the lipid peroxidation in either sex during the period of thiamine deficiency. It appears that thiamine intake is an important determination in drug metabolism and lipid peroxidation.

Acetanilides↗
PubMed1990

Differences in induction of hepatic cytochrome P450 isozymes by mice in eight methylenedioxyphenyl compounds.

Eight methylenedioxyphenyl (MDP) compounds were examined for their ability to induce cytochrome P450 (P450) in mouse liver. Induction by safrole, isosafrole, and dihydrosafrole was studied in both C57BL/6N (Ah-responsive) and DBA/2N (Ah-nonresponsive) male mice after IP administration of 200 mg/kg/day MDP compound for 3 days. Hepatic P450 content, ethylmorphine N-demethylase, ethoxy-resorufin O-deethylase, and acetanilide hydroxylase activities were induced to the same extent in both strains of mice. Benzo(a)pyrene hydroxylase activity, however, was not induced in either C57 or DBA mice. The similarity of results in both strains of mice indicated induction of these P450 isozymes by these three MDP compounds is not mediated by the Ah receptor. Induction of P450 by butylbenzodioxole (n-butyl-BD), tertiarybutylbenzodioxole (t-butyl-BD), methylbenzodioxole (methyl-BD), nitrobenzodioxole (nitro-BD), and bromobenzodioxole (bromo-BD) was examined only in C57BL/6N mice. Methyl-BD, nitro-BD, and bromo-BD did not induce hepatic microsomal proteins or selected P450 monooxygenase activities. In contrast, n-butyl-BD, and t-butyl-BD induced P450 content, ethylmorphine N-demethylase, acetanilide hydroxylase, and ethoxyresorufin O-deethylase activities. Benzo(a)pyrene hydroxylase was not induced by any of the treatments. Induction of these P450 activities is consistent with induction of P450 IIB1 and P450 IA2, but not induction of P450 IA1. Western blot analysis with antibodies to P450 isozymes induced with either phenobarbital (Pb) or 3-methylcholanthrene (3-MC) confirmed that both IIB1 and IA2 were induced, but that IA1 was not induced.

Animals↗
PubMed1985

Binding of dapsone and its analogues to human serum albumin.

The binding of dapsone, 4,4'-sulfonylbis(aniline)(1), and its diacetylated derivative, 4,4"'-sulfonylbis(acetanilide)(2), to human serum albumin is reported. To assess the ability of these compounds to displace 4'-[(4-aminophenyl)sulfonyl]acetanilide (3) from albumin, a dialysis rate technique was used. Competition for the bilirubin binding site on albumin was measured with the peroxidase assay. Compounds 1 and 2 strongly displaced both 3 and bilirubin from human serum albumin. The association constants for 1 and 2 with respect to bilirubin binding were 1.29 X 10(3) and 1.15 X 10(4) M-1, respectively. These results suggest that the binding site for 3 and the bilirubin binding site are similar with respect to 1 and 2 and that the binding of dapsone and its derivatives probably does not involve the amino function.

Dapsone↗
PubMed1999

Deuterium REDOR: principles and applications for distance measurements

The application of short composite pulse schemes ( and ) to the rotational echo double-resonance (REDOR) spectroscopy of X-2H (X: spin 12, observed) systems with large deuterium quadrupolar interactions has been studied experimentally and theoretically and compared with simple 180 degrees pulse schemes. The basic properties of the composite pulses on the deuterium nuclei have been elucidated, using average Hamiltonian theory, and exact simulations of the experiments have been achieved by stepwise integration of the equation of motion of the density matrix. REDOR experiments were performed on 15N-2H in doubly labeled acetanilide and on 13C-2H in singly 2H-labeled acetanilide. The most efficient REDOR dephasing was observed when composite pulses were used. It is found that the dephasing due to simple 180 degrees deuterium pulses is about a factor of 2 less efficient than the dephasing due to the composite pulse sequences and thus the range of couplings observable by X-2H REDOR is enlarged toward weaker couplings, i.e., larger distances. From these experiments the 2H-15N dipolar coupling between the amino deuteron and the amino nitrogen and the 2H-13C dipolar couplings between the amino deuteron and the alpha and beta carbons have been elucidated and the corresponding distances have been determined. The distance data from REDOR are in good agreement with data from X-ray and neutron diffraction, showing the power of the method. Copyright 1999 Academic Press.

Journal Article↗