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PubMed1983

The superiority of hamster liver microsomal fraction for activating nitrosamines to mutagens in Salmonella typhimurium.

A number of nitrosamines which were carcinogenic in rats were not activated to mutagens in the Salmonella/mammalian microsome assay by the addition of the rat liver microsomal fraction. Some of these nitrosamines induced tumors in the liver of rats and others were carcinogenic to different organs of the rat. Most of these nitrosamines were activated to mutagens by hamster liver microsomal fraction. The use of the hamster preparation showed some compounds to be of very high mutagenic potency. In a few cases the nitrosamines mutagenic with hamster liver activation were more potent carcinogens in the hamster than in the rat. The compounds which were non-mutagenic to Salmonella with either rat or hamster liver activation included the liver carcinogens nitrosomethylethylamine, nitrosodiethanolamine and nitrosoethanolisopropanolamine, the esophageal carcinogens nitrosomethylneopentylamine, nitrosomethylaniline, nitrosomethyl-4-fluoroaniline, nitrosothiomorpholine and nitrosophenylbenzylamine, and the bladder carcinogens nitrosomethyl-3-carboxypropylamine and nitrosodiphenylamine.

Animals↗
PubMed1985

Tissue-specific inhibition of [3H]thymidine incorporation into DNA by carcinogenic N-nitrosamines.

The N-nitrosamines N-nitrosodimethylamine (DMN), N'-nitrosonornicotine (NNN) and 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone (NNK) were injected intraperitoneally 24 h before sacrifice in F344 rats and C57BL mice in doses of 297 mumoles/kg b.w. and 148 mumoles/kg b.w., respectively. 2 h before sacrifice, the animals were given an intraperitoneal injection of [3H]thymidine. The results showed that the examined N-nitrosamines inhibited the incorporation of [3H]thymidine into DNA in a few tissues of the rats and the mice. The results indicated that the N-nitrosamines exerted a tissue-specific inhibition of the [3H]thymidine incorporation in the tissues reported to be involved in the biotransformation of these substances. The observed inhibitory effects on the incorporation of [3H]thymidine by DMN, NNN and NNK were also correlated to a considerable extent to the reported sites of carcinogenicity. The present study indicates that measurements of [3H]thymidine incorporation into DNA in various tissues of experimental animals is a useful short-term bioassay to evaluate the potential tissue-specific carcinogenicity of the N-nitrosamines. The method may also be useful as a complement to other short-term in vivo tests in the screening of potential genotoxicity of several other chemicals.

Animals↗
PubMed1985

The derivation of nitrosamines from some therapeutic amines in the human environment.

Five therapeutic drugs which are secondary and tertiary amines were investigated by reaction mechanisms for the derivation of nitrosamines in the human environments. These drugs are chlorpromazine (tranquilizer), methadone (analgesic), chloroquine (antimalarial), primaquine (antimalarial), and phenacetin (analgesic). Phenacetin is an N-acetylated secondary amine; chloroquine and primaquine are secondary amines; methadone and chlorpromazine are tertiary amines; and chloroquine is also a tertiary amine. In the human environments of the gastrointestinal tract, stomach, and bladder which generate the nitrosating agent, the derivation of various nitrosamines from these drugs has been presented. Dimethyl nitrosamine has been derived from methadone and diethylnitrosamine has been generated from chlorpromazine and chloroquine, respectively. Chlorpromazine, methadone, chloroquine, primaquine, and phenacetin have also produced by reaction mechanisms various nitrosamines of hitherto unknown carcinogenicity. The dimethylnitrosamine and diethylnitrosamine derived from methadone, chlorpromazine, and chloroquine are of proven carcinogenicity in experimental animals and they therefore constitute a hazard to humans.

Amines↗
PubMed1979

Derivatives of side-chain hydroxylated nitrosamines direct acting mutagens in Salmonella typhimurium.

Methyl-(beta-tosyloxyethyl)nitrosamine and 3-methyl-4,5-dihydro-1,2,3-oxadiazolium tosylate are potent direct acting mutagens in the Ames assay, as is N-nitrosoprolinyl tosylate. These compounds are derived from beta-hydroxylated nitrosamines. The closely related methyl-(gamma-tosyloxypropyl)nitrosamine is not mutagenic without activation. These data are consistent with the chemical behavior of these substances, which suggest that suitable derivatives of beta-hydroxylated nitrosamines, such as O-sulfates, may be direct-acting biological alkylating agents.

Dose-Response Relationship, Drug↗
PubMedDate not supplied

Metabolic activation capabilities of S9 and hepatocytes from uninduced rats to convert carcinogenic N-nitrosamines to mutagens.

6 carcinogenic nitrosamines were studied in Salmonella typhimurium TA1535 after activation by S9 and by hepatocytes. All nitrosamines were activated by S9 from induced rats, regardless of their organotropy. The hepatocarcinogenic nitrosamines (N-nitrosodimethylamine, NDMA; N-nitrosodiethylamine, NDEA; N-nitrosomorpholine, NM and N-nitrosodibutylamine, NDBA) were activated to mutagens by S9 and by hepatocytes both derived from noninduced rat livers, NDMA and NM inducing more his+ revertants in the presence of hepatocytes. The oesophageal carcinogenic nitrosamine N-nitrosomethylbenzylamine (NMBeA) and bladder organotrophic N-nitroso(4-hydroxybutyl)butylamine(NBBOH) were neither converted by liver preparations of uninduced rats into mutagenic intermediates nor by hepatocytes. This study indicates that isolated cells derived from untreated animals may be better suited to study liver specific activation in vitro than disrupted subcellular metabolizing systems from induced animals.

Animals↗
PubMed1984

Survey of human milk for volatile N-nitrosamines and the influence of diet on their formation.

Human milk was analysed for volatile N-nitrosamines and the influence of diet on their possible presence and formation was assessed. 175 samples were obtained from 16 different nursing women. Analysis of samples collected at random, to ascertain baseline levels, indicated that 76.5% of the human milk samples contained less than 0.2 ppb N-nitrosodimethylamine (minimum level of reliable measurement). No other volatile nitrosamines were detected. Expressed milk was collected from volunteers over a 6-hr period after eating meals which included bacon (a source of performed nitrosamines) and at times a vegetable high in nitrate. Eating a meal containing bacon did not result in increased nitrosamine levels in milk. In certain individuals, eating a meal of bacon and a vegetable high in nitrate occasionally resulted in higher levels of N-nitrosodimethylamine in their milk.

Chromatography, Gas↗
PubMed1984

Is there a local production of nitrosamines by the vaginal microflora in anaerobic vaginosis/trichomoniasis?

Nitrosamines have been identified in vaginal secretions of women with trichomoniasis. Both nitrites and amines the elements for nitrosamine synthesis are produced by the abnormal-predominantly anaerobic-vaginal flora of patients with bacterial vaginosis/trichomoniasis. The final formation of nitrosamines could also depend on microbial enzymatic activity. The confirmation of an endogenous generation of oncogenic nitrosamines in the vaginas of some women could give promising impulses to cancer-research concerning the uterine cervix.

Anaerobiosis↗
PubMed2005

Automated solid-phase extraction and high-performance liquid chromatographic determination of nitrosamines using post-column photolysis and tris(2,2'-bipyridyl) ruthenium(III) chemiluminescence.

A sensitive and selective post-column detection system for nitrosamines is described. The principle upon which the detector works is that UV irradiation of aqueous solutions of nitrosamines leads to cleavage of the N-NO bond. The amine generated is subsequent detected by chemiluminescence using tris(2,2'-bipyridyl) ruthenium(III), which is on-line generated by photo-oxidation of the ruthenium(II) complex in the presence of peroxydisulfate. Factors affecting the photochemical and chemiluminescent reactions were optimized to minimise their contribution to the total band-broadening. This detection system was tested for N-nitrosodimethylamine, N-nitroso-diethylamine, N-nitrosomorpholine, N-nitrosopiperidine and N-nitrosopyrrolidine, which were separated on an ODS column by isocratic reversed-phase chromatography with acetonitrile-water containing 5 mM acetate buffer at pH 4.0. A linear relationship between analyte concentration and peak area was obtained within the range 0.13-500 microg l(-1) with correlation coefficients greater than 0.9995 and detection limits of between 0.03 and 0.76 microg l(-1). Intra- and inter-day precision values of about 1.2% RSD (n = 11) and 2.5% RSD (n = 10), respectively, were obtained. The sensitivity may increase from 9 to 280 times with respect to UV detection, depending on the nitrosamine in question. An automated solid-phase extraction (SPE) system was used in conjunction with HPLC to determine nitrosamine residues in waters. Detection limits within the range 0.10-3.0 ng l(-1) were achieved for only 250 ml of sample.

2,2'-Dipyridyl↗
PubMed1976

Selective detection of N-nitrosamines by gas chromatography using a modified microelectrolytic conductivity detector in the pyrolytic mode.

The pyrolysis of nitrosamines in a modified Hall microelectrolytic conductivity system provides the basis for a highly selective and sensitive determination method. Under the conditions specified, the response of this detector system to nitrosamines is at least 10(7) times greater than that for n-hexane. The influence of several operational parameters on the response of the detector to nitrosamines was studied. For open-chain nitrosamines, the detection limit is 50 pg and the response is linear up to at least 200 ng.

Chromatography, Gas↗
PubMed1987

Determination of nitrosamines by liquid chromatography with post-column photolysis and electrochemical detection.

The liquid chromatographic detection of nitrosamines at the ppb (10(9)) and sub-ppb levels is still a difficult problem. A significant improvement was achieved when a nitrosamine eluted from the column was photolysed by a UV lamp, the charged nitrite species being detected amperometrically. N-Nitrosodimethylamine (NDMA) was selected as a model solute to test the applicability of the detection device. The calibration graphs were linear over a wide concentration range. Optimal detection depended on the nature of the buffer used and the UV spectrum of the nitrosamine to be detected. An interesting application of the detection of a high-molecular-weight nitrosamine is given as an example.

Beer↗
PubMed2002

Optimization of parameters for the supercritical fluid extraction in the determination of N-nitrosamines in rubbers.

The study of the possibilities of supercritical fluid extraction (SFE) with N-nitrosamines in rubbers has been carried out. Home-made materials fortified with several N-nitrosamines were prepared in order to optimize the SFE parameters. A Plackett-Burman design was employed to evaluate the influence of those parameters to be controlled in SFE, such as pressure, temperature, static and dynamic time, restrictor temperature and volume of modifier while CO2 was used as the extraction fluid. An extra central composite design for the main factors (according to the previously obtained results) was also developed in order to refine the best supercritical conditions for the extraction of N-nitrosamines from rubbers. Gas chromatography with a nitrogen and phosphorus sensitive detector was used to achieve sensitivity and limits of detection for the concentrations expected in plastic materials. The proposed analytical method has shown to be useful in the determination of N-nitrosamines even for complex matrices.

Chromatography, Supercritical Fluid↗
PubMed2003

Determination of nitrosamines in preserved sausages by solid-phase extraction-micellar electrokinetic chromatography.

A new methodology for extraction, pre-concentration and analysis of nitrosamines in meat derived products was developed. The samples (canned sausages) were distilled in vacuum steam and the nitrosamines were pre-concentrated by solid-phase extraction with active carbon. Then, micellar electrokinetic chromatography was used for the separation and determination of the different nitrosamines contained in a real sample and gas chromatography with mass spectrometry detection was used as the confirmation technique. The method allowed the determination of nitrosamine compounds at trace levels with relative standard deviation ranging from 4.0 to 22%.

Animals↗
PubMed1999

DNA adduct formation from tobacco-specific N-nitrosamines.

Tobacco-specific N-nitrosamines are a group of carcinogens derived from the tobacco alkaloids. They are likely causative factors for cancers of the lung, esophagus, pancreas, and oral cavity in people who use tobacco products. The most carcinogenic tobacco-specific nitrosamines in laboratory animals are 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL), and N'-nitrosonornicotine (NNN). DNA adduct formation from NNK and NNN has been studied extensively and is reviewed here. NNK is metabolically activated by cytochromes P450 to intermediates which methylate and pyridyloxobutylate DNA. The resulting adducts have been detected in cells and tissues susceptible to NNK carcinogenesis in rodents. The methylation and pyridyloxobutylation pathways are both important in carcinogenesis by NNK. NNK also induces single strand breaks and increases levels of 8-oxodeoxyguanosine in DNA of treated animals. NNAL, which like NNK is a potent pulmonary carcinogen, is also metabolically activated to methylating and pyridyloxobutylating intermediates. NNN pyridyloxobutylates DNA in its rat target tissues, esophagus and nasal mucosa. Methyl and pyridyloxobutyl DNA adducts are detected in human tissues. The methyl adducts most likely result in part from exposure of smokers to NNK, but these adducts are also detected in non-smokers. Some of the methyl adducts detected in non-smokers may be due to environmental tobacco smoke exposure. There are also potential dietary and endogenous sources of these adducts. Pyridyloxobutyl DNA adducts in human tissues result mainly from exposure to tobacco-specific N-nitrosamines. In laboratory animals, DNA adduct formation and carcinogenicity of tobacco-specific N-nitrosamines are closely correlated in many instances, and it is likely that similar relationships will hold in humans.

Animals↗
PubMed2001

Attempt to adsorb N-nitrosamines in solution by use of zeolites.

The strong adsorption of zeolite for N-nitrosamines in solution was first revealed by use of adsorption, and temperature programmed surface reaction (TPSR) techniques. N-nitrosodimethylamine (NDMA) and N-nitrosopyrrolidine (NPYR) as well as N-nitrosohexamethyleneimine (NHMI) can be adsorbed on zeolite Y, ZSM-5 and A in the solution of methylene chloride or water, which will be helpful for removal of the N-nitrosamines pollution in environmental protection. The equilibrium data were fitted to Freundlich-type isotherms, but the adsorption capacity of zeolites mainly depended on their pore size, surface area and acid-basic properties. Molecular size of adsorbate and solute-solvent interaction also strongly affected the adsorption of N-nitrosamines on zeolite in solution. The extraordinary adsorption properties of NaA zeolite for N-nitrosamines in aqueous solution is first reported and discussed.

Adsorption↗
PubMed2000

Excretion of volatile nitrosamines in a rural population in relation to food and drinking water consumption.

Urinary excretion of volatile nitrosamines was assessed in 59 non-smokers living in a rural county of Québec, Canada. Water and food intakes were measured by means of a 24-hour recall. Nitrates were analyzed in the tap water of all participants (geometric mean=2.0 mg nitrate-N/L) and dietary intakes of nitrate and vitamins C and E were estimated via a validated Canadian food database. Urine was collected over the same 24-hour period and analyzed for nitrates by hydrazine reduction and for volatile nitrosamines by gas-chromatography/mass spectrometry. N-Nitrosopiperidine (NPIP) was found in urine samples from 52 of the 59 subjects. Geometric mean of NPIP urinary excretion was 67 ng/day and maximum value was 1045 ng/day. No other volatile nitrosamine was detected. There was a correlation between urinary nitrate excretion and total nitrate intake (r=0.71, P < 0.001). However, no relationship was found between urinary NPIP excretion and either nitrate excretion, dietary or water nitrate intakes. NPIP excretion was significantly correlated to coffee intake (r=0.40, P=0.002) and this relation was not modified by vitamin intake. We conclude that nitrate intake is not related to nitrosamine excretion in this rural population. The influence of coffee consumption on NPIP excretion deserves further attention.

Adult↗
PubMed2001

Asymmetric transformation of N-nitrosamines by inclusion crystallization with optically active hosts.

Several N-nitrosopiperidines with chirality solely due to a hindered rotation about the N-N bond were resolved to enantiomers by inclusion crystallization with optically active diols (TADDOLs). The absolute configuration of the guest nitrosamines was deduced from the X-ray crystal structures of the inclusion complexes. The enclathrated nitrosamines were liberated by a competitive complexation of the host diols with piperazine. The optical activity of the resolved nitrosamines is manifested by their CD spectra. A simple chirality rule was proposed for a rationalization of the observed Cotton effect sign corresponding to the n-pi* electronic transition. The optically active nitrosamines are configurationally labile compounds and gradually racemize in solution but they are indefinitely stable in the solid state. The first-order kinetics of the racemization in solution allowed us to assign the N-N rotation barriers by simple polarimetric measurements.

Crystallization↗
PubMedDate not supplied

Mass spectrometric analysis of tobacco-specific nitrosamine-DNA adducts in smokers and nonsmokers.

A gas chromatography, negative ion chemical ionization mass spectrometry (GC-NICI-MS) based assay for tobacco-specific nitrosamine adducts of DNA is described. The assay is based on the observation that acid hydrolysis of DNA from animals treated with tobacco-specific nitrosamines releases 4-hydroxy-1-(3-pyridyl)-1-butanone (HPB). HPB and the internal standard [4,4-D2]HPB are derivatized with pentafluorobenzoyl chloride and the resulting HPB-pentafluorobenzoate is purified by high-performance liquid chromatography prior to GC-NICI-MS analysis. DNA from human peripheral lung and tracheobronchial tissue, collected at autopsy, was analyzed for acid-released HPB. The mean HPB level (fmol/mg of DNA) for peripheral lung DNA was 11 +/- 16 (SD, n = 9) for smokers and 0.9 +/- 2.3 (n = 8) for nonsmokers. Mean adduct levels in tracheobronchus were 16 +/- 18 (n = 4) for smokers and 0.9 +/- 1.7 (n = 4) for nonsmokers. These are the first measurements of tobacco-specific nitrosamine-DNA adducts in humans. Further studies comparing the levels of DNA and globin adducts will provide a better understanding of the metabolic activation of tobacco-specific nitrosamines in humans and may provide a more accurate indication of an individual's risk of developing tobacco-related cancer.

Adolescent↗