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At least 19 recordsLinked to original sources
PubMed1976

Mechanism of 2-naphthylamine oxidation catalysed by pig liver microsomes.

1. In pig liver microsomes 2-naphthylamine-dependent NADPH oxidation, oxygen reduction, and hydroxylamine formation are linear with time for several minutes. A sharp increase in NADPH oxidation and oxygen uptake then coincides with an abrupt loss of hydroxylamine from the medium. 2. The initial rate of 2-naphthylamine N-oxidation correlates with the microsomal concentration of mixed-function amine oxidase and the extent of linear accumulation of hydroxylamine is dependent on microsomal NADPH-cytochrome c reductase activity and concentration of lipid (microsomes). 3. Antisera to NADPH-cytochrome c reductase markedly decreased hydroxylamine accumulation during incubation but had no effect on the rate of 2-naphthylamine N-oxidation. 4. A system duplicating all of the kinetic properties of the microsomal 2-naphthylamine oxidase was constructed with two purified flavoproteins, (mixed-function amine oxidase and NADPH-cytochrome c reductase) and a lipid phase (erythrocyte ghosts or synthetic lecithin liposomes). 5. By independently varying the concentrations of each component in the reconstituted system, the contribution of each to the observed kinetics was defined. 6. In addition to the initial N-oxidation of 2-naphthylamine, at least six other reactions contribute to the kinetic patterns of 2-naphthylamine oxidation catalysed by the reconstituted system.

2-Naphthylamine↗
PubMed1977

Hepatic microsomal N-glucuronidation and nucleic acid binding of N-hydroxy arylamines in relation to urinary bladder carcinogenesis.

Uridine 5'-diphosphoglucuronic acid-fortified hepatic microsomes from dogs, rats, or humans rapidly metabolized [3H]-N-hydroxy-2-naphthylamine (N-HO-2-NA) to a water-soluble product that yielded 98% of the parent N-hydroxy amine upon treatment with beta-glucuronidase. The metabolite was identified as N-(beta-1-glucosiduronyl)-N-hydroxy-2-naphthylamine from ultraviolet, infrared, and mass spectral analyses of the glucuronide and its nitrone derivative. Incubation of N-hydroxy-1-naphthylamine (N-HO-1-NA), N-hydroxy-4-aminobiphenyl (N-HO-ABP), or the N-hydroxy derivatives of 2-aminofluorene, 4-aminoazobenzene, or N-acetyl-2-aminofluorene with uridine 5'-diphosphoglucuronic acid-fortified hepatic microsomes also yielded water-soluble products. beta-Glucuronidase treatment released 80 to 90% of the [3H]-NHO-1-NA and [3H]-N-HO-ABP conjugates as tritiated ether-extractable derivatives. N-HO-1-NA, N-HO-2-NA, and N-HO-ABP and the glucuronides of these N-hydroxy arylamines were relatively stable and nonreactive near neutral pH. At pH 5, the N-glucuronide of N-HO-2-NA and the presumed N-glucuronides of N-HO-1-NA and N-HO-ABP were rapidly hydrolyzed to the N-hydroxy arylamines that were then converted to reactive derivatives capable of binding covalently to nucleic acids. These data support the concept that arylamine bladder carcinogens are N-oxidized and N-glucuronidated in the liver and that the N-glucuronides are transported to the urinary bladder. The hydrolysis of the glucuronides to N-hydroxy arylamines and the conversion of the latter derivatives to highly reactive electrophilic arylnitrenium ions in the normally acidic urine of dogs and humans may be critical reactions for tumor induction in the urinary bladder.

Animals↗
PubMed1978

Frequent elevation of tissue polypeptide antigen in the sera of workers exposed to bladder carcinogens.

A group of 108 male workers previously exposed to bladder carcinogens and a group of 26 patients with carcinoma of the bladder differed significantly from a control group comprising 63 healthy male donors with respect to their levels of tissue polypeptide antigen (TPA). The risk group exhibited 4-6 times more frequent elevations of TPA than did the group of healthy donors.

2-Naphthylamine↗
PubMed1979

Immunosurveillance in pre-malignant occupational bladder disease.

A population of workers exposed to bladder carcinogens has been studied by comparing their immunoreactivity against bladder cancer cells and against a control cancer cell with that found in normal individuals and in patients with bladder cancer. Data are presented which indicate equivalent increases in specific reactivity against bladder cancer cells in clinically normal carcinogen-exposed workers and in patients with bladder cancer. Increases in reactivity are related to degree of exposure and also to early malignant changes in the urothelium. This indicates that immune recognition of tumour antigens does occur before development of overt malignancy.

1-Naphthylamine↗
PubMed1979

The histochemical localisation of aminopeptidases in the central nervous system and an analysis of factors contributing to the final staining pattern.

A method is described for the localisation of aminopeptidases in the central nervous system. The enzymatic cleavage of the peptide bond in the substituted naphthylamide substrates results in the liberation of free naphthylamine which in the presence of an azo salt can be precipitated as a blue dye at sites of enzyme activity. Analysis of different brain regions using this technique indicates that these enzymes may have a specific function at certain sites in the CNS. Since this is the first method to produce any localised staining in nervous tissue an analysis of factors contributing to the final staining pattern is also presented.

2-Naphthylamine↗
PubMed1977

Aminotetralins as selective beta-adrenergic agonists.

Aminotetralin derivatives M-8 and JOD-176, were studied in relation to isoproterenol for beta-adrenergic activity. M-8 and JOD-176 were found to be very weak in activating cardiac beta-receptors. These compounds were also found to be considerably more active in uterine and bronchial smooth muscle. Because these compounds were also shown to be very inactive in vascular smooth muscle, the possibility that beta-receptors in different smooth muscle types may also differ was suggested.

1-Naphthylamine↗
PubMed1975

N-Isopropyl derivatives of dopamine and 5,6-dihydroxy-2-aminotetralin.

Secondary and tertiary amino homologs of the title compounds have been prepared, bearing an N-isopropyl group. In peripheral evaluation, certain members of the series exhibited beta-adrenergic agonist effects of lower activity than isoproterenol. N-Methyl-N-isopropyl-5,6-dihydroxytetralin exhibited marked properties consistent with its being an alpha agonist, and it is concluded that introduction of considerable bulk about the nitrogen of a catecholamine does not a priori destroy alpha-agonist effects. The compounds qualitatively paralleled the effects of dopamine in assays based upon direct intrastriatal administration in rats, although they were less potent than dopamine.

2-Naphthylamine↗
PubMed1976

Studies on the chemical nature of urinary chemiluminescence.

Studies on the nature of the chemicals responsible for urinary chemiluminescence have been carried out. Urinary chemiluminescence can be increased slightly by sulphatase, more by glucuronidase but most of all by boiling for 1 hour at pH 1. It is suggested that most of the chemicals responsible for urinary chemiluminescence are bound as non-chemiluminescent precursors to sulphate, glucuronic acid and in other ways. Both the chemiluminescent material and the inactive precursors are freely ultrafiltrable with molecular weights below 500. A survey of various chemicals has revealed considerable chemiluminescence in certain metabolites of naphthylamines and known to cause bladder cancer but little or no chemoluminescence in the tryptophane metabolites that have been thought to cause bladder cancer.

1-Naphthylamine↗
PubMed1979

Ozonation of mutagenic and carcinogenic polyaromatic amines and polyaromatic hydrocarbons in water.

The Salmonella-microsome assay for mutagenesis was used to determine the effect of ozone on the mutagenesis of selected carcinogens and mutagens in water. Short periods of ozonation were shown to completely inactivate the mutagenicity of several polyaromatic amine mutagens including acriflavine, proflavine, and beta-naphthylamine. Selected polyaromatic hydrocarbons were also sensitive to ozonation. Kinetic studies revealed that the mutagenicity of benzo(a)pyrene, 3-methylcholanthrene, and 7,12-dimethylbenz(a)anthracene was destroyed after short periods of ozonation. To correlate loss of mutagenicity with loss of carcinogenicity, two polyaromatic hydrocarbons were treated with ozone, extracted from water with hexane, and tested for carcinogenicity in mice. When 7,12-dimethyl-benz(a)anthracene and 3-methyl-cholanthrene were treated with ozone, there was a substantial reduction in carcinogenicity compared to control groups treated with oxygen alone. However, a small number of tumors developed in the group of animals receiving a hexane extract of ozonated 7,12-dimethylbenz(a)anthracene. This activity may be due to breakdown products of 7,12-dimethylbenz(a)anthracene that are not mutagenic.

2-Naphthylamine↗
PubMed1977

Flow cytometric measurement of peptidases with use of 5-nitrosalicylaldehyde and 4-methoxy-beta-naphthylamine derivatives.

Enzyme activity can be measured in single cells or in cell suspensions by either static or flow microfluorometry when a fluorogenic substrate is used. We have used amino acid derivatives of arylamines as fluorogenic substrates for tagging cellular proteinases. The liberated aromatic amine, which can diffuse from the cell, is trapped as a fluorescent insoluble Schiff-base product with 5-nitrosalicylaldehyde, with the peak of fluorescence emission shifted from lambdaem 425 nm to lambdaem 530 and 595 nm. Although the reaction is faster at pH 4 than at higher pH's, the equilibrium during the assay of certain peptidase activities is such that the liberated aromatic amine is trapped in the cell at pH values as high as 7.5. 5-Nitrosalicylaldehyde causes almost no inhibition of substrate hydrolysis at 1 mmol/liter, a concentration exceeding that required for complete trapping of reaction product. The kinetics of enzymatic reactions with four synthetic substrates are demonstrated in intact Balb 3T3 cells and sonicated preparations in the presence of 5-nitrosalicylaldehyde. Hydrolytic rates for the substrate, CBZ-ala-arg-arg-4-methoxy-beta-naphthylamine, are given for single 3T3 cells by microfluorophotometry and for suspensions of 3T3 cells by flow cytometry. The clinical value of the method is demonstrated for differentiating mixed populations of leukocytes.

2-Naphthylamine↗
PubMed1978

[Hypotensive and antihypertensive activity of a newly synthesized derivative of 2-aminotetralin].

The report describes the hypotensive and antihypertensive activity of the compound N-(trans-3-hydroxy-1,2,3,4-tetrahydro-2-naphtyl)-N'-(3-oxo-3-phenylpropyl) piperazine dihydrochloride (P11). The work is made on normotensive cats and rats as well as on spontaneous and experimental (metacorticoid) hypertension. The studies were carried out under the conditions of acute and chronic experiment as the arteria pressure was recorded by blood and bloodless method. The compound P11 show a manifested hypotensive activity with favourable duration and therapeutic width. Its antihypertensive activity is revealed in rats with spontaneous and metacorticoid hypertension both after single and chronic applciation of the compound. The influence on the blood pressure weakens after reserpinization of the animals. The compound possesses slight ganglion-blocking action and manifested alpha and beta adreno-blocking activity: diminishes noradrenaline, adrenaline and isoprenaline responses on the arterial pressure and heart activity in anesthetised cats and rats, shifts to the right the cumulative dose-response curve of noradrenaline on vas deferens of a rat, ect. The hypotensive and antihypertensive effect of the compound P11 is discussed on the basis of its alpha and beta adrenoblocking action and its specific sedative effect.

2-Naphthylamine↗
PubMed1979

[Antihistamine and antiserotonin action of 2 aminotetralin derivatives].

The authors performs studies under the conditions of whole organism in vivo and on isolatid organs in vitro and examined antihistamine and antiserotonine activity of two derivatives of 2-aminotetraline, synthesized by D. Dancev and Iv. Ivanov, namely: N-(trans-e-hydroxy-1, 2, 3, 4-tetrahydro-2-naphtyl (-N-) 3-oxo-3-phenylpropyl) piperasine dichloride and N-(trans-3-hydroxy-1, 2, 3, 4-tetrahydro-2-naphtyl (-N-) 3-oxo-3-3phenyl-2-methylpropyl (piperasine dichloride) indicated respectively as P10 and P11. The experiments on isolated ileum of a guinea pig showed that the compound P11 (in concentration of 1.10(-7), 1.10(-6), and 1.10(-5) gm/ml) and P11 (in concentration of 1.10(-6) and 1.10(-5) gm/ml) inhibited the spasomogenic effect of histamine (1.10(-8) and 1.10(-7) gm/ml) as better antihistaminev effect revealed P10. Both compounds inconcentrations of 1.10(-6) and 1.10(-5) gm/ml inhibited the spasmogenic effect of serotonine (1.10(-7) gm/ml), as more significant changes occurred under the influence of the compound P11. The compound P10, administered subcutaneously in a guinea pig in a dose of 0.5 mg/kg of body weight 30 minutes before the occurrence of histamine shock, prevented its development. The same compound inhibited also the development of enterocolitis in mice, induced by serotonine (in a dose of 1 mg/kg of body weight). Both examined compounds inhibited the development of serotonine oedema of the hind paw of a rat as better effect showed the compound P11. The established facts are discussed.

2-Naphthylamine↗