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PubMed1988

Chronic atrophic gastritis and risk of N-nitroso compounds carcinogenesis.

Chronic atrophic gastritis is considered a precancerous condition for carcinoma of the stomach. To evaluate the correlation between progressive alterations in the mucosa and gastric juice microenvironmental factors, retained involved on N-nitroso compounds carcinogenesis, detailed analyses of biochemical and microbiological parameters such as pH, total viable counts (TVC), nitrate reductase positive bacterial counts (NRPBC), nitrite (NO2-) and thiocyanate (SNC-) levels, were carried out on 56 fasting gastric juices samples obtained at endoscopy from 28 patients with chronic atrophic gastritis (CAG), 14 with gastric cancers (GC), and 14 normal controls (NC). The mean values of pH, nitrite, TVC, and NRPBC were significantly lower in the juices of NC than in those of CAG and GC patients. Furthermore, the mean levels of the same parameters were higher in GC than in CAG juices. No significant difference was found in the three groups for SCN- level which principally resulted influenced by smoke habit. The 28 patients with CAG were subdivided into two groups (Group A = Diffuse chronic atrophic gastritis--DCAG; Group B = Multifocal chronic atrophic gastritis--MCAG) according to the involvement of gastric corpus and fundus besides antrum by a process of mucosal atrophy. The mean levels of pH, nitrite, TVC, and NRPBC were significantly higher in MCAG than in normal controls but statistically lower in reference to DCAG and cancers. In these two groups no difference was found for the same variables. The percentage of contaminated juices was higher for DCAG and cancers in respect to MCAG but no difference was found between DCAG and neoplastic stomachs. The results of this study suggest that the DCAG could be considered as the chronic atrophic gastritis type more exposed to the risk of N-nitroso compounds carcinogenesis.

Adult↗
PubMed2006

The effect of haem in red and processed meat on the endogenous formation of N-nitroso compounds in the upper gastrointestinal tract.

Red and processed meat (PM) consumption increases the risk of large bowel cancer and it has been demonstrated that haem in red meat (RM) stimulates the endogenous production of N-nitroso compounds (NOCs) within the human intestine. To investigate whether N-nitrosation occurs in the upper gastrointestinal tract, 27 ileostomists were fed diets containing no meat, or 240 g RM or 240 g PM in a randomly assigned crossover intervention design carried out in a volunteer suite. Endogenous NOC were assessed as apparent total N-nitroso compounds (ATNC) in the ileostomy output. ATNC concentration in the diets was 22 microg ATNC/kg (RM) and 37 microg ATNC/kg (PM), and 9 microg ATNC/kg in the no meat diet. Levels significantly increased to 1175 microg ATNC/kg SEM = 226 microg ATNC/kg) following the RM (P=0.001) and 1832 microg ATNC/kg (SEM=294 microg ATNC/kg) following PM (P<0.001) compared to the no meat diet (283 microg ATNC/kg, SEM=74 microg ATNC/kg). ATNC concentrations in the ileal output were equivalent to those measured in faeces in similarly designed feeding studies. Supplementation with either 1 g ascorbic acid or 400 IU alpha-tocopherol had no effect on the concentration of ATNC detected in the ileal output. In in vitro experiments, N-nitrosomorpholine (NMor) was formed in the presence of nitrosated haemoglobin, at pH 6.8 but not in the absence of nitrosated haemoglobin. These findings demonstrate that haem may facilitate the formation of NOC in the absence of colonic flora in the upper human gastrointestinal tract.

Animals↗
PubMed1999

Interference by S-nitroso compounds with the measurement of nitrate in methods requiring reduction of nitrate to nitrite by cadmium.

Various methods suited for the measurement of nitrate require its reduction to nitrite by cadmium under acidic or alkaline conditions. N(G)-Nitroarginine analogs have been shown to interfere with the measurement of nitrate by such assays. In the present work we show by gas chromatography-mass spectrometry that under alkaline reduction conditions the S-nitroso compounds S-nitrosoglutathione and S-nitrosohomocysteine but not S-nitroso-N-acetylcysteine and S-nitroso-N-acetylpenicillamine can considerably contribute to nitrate and thus interfere with its measurement. Our results suggest that S-nitroso compounds may interfere with the measurement of nitrate in methods requiring cadmium-catalyzed reduction of nitrate to nitrite.

Cadmium↗
PubMed1984

The influence of enterogastric reflux on gastric juice bacterial growth, nitrite, and N-nitroso compound concentrations following gastric surgery.

Detailed analyses were carried out in 207 fasting gastric juice samples obtained at endoscopy or with a nasogastric tube from 50 patients with partial gastrectomy, 43 with vagotomy, 20 with gastric carcinoma and 50 controls. Significantly higher mean pH, nitrite and N-nitroso compound (N-NO) concentrations and nitrate-reducing bacterial cultures were noted following partial gastrectomy compared with normal controls and comparable to findings in gastric cancer. A highly significant relationship (p less than 10(-6)) was also demonstrated between pH and N-NO concentrations, highest levels of which were seen following Billroth II gastrectomy, significantly higher (p = 0.02) than Billroth I, whereas the only change observed following proximal gastric vagotomy was a nearly threefold rise in N-NO compared with normal controls. However, vagotomy and pyloroplasty produced gastric juice changes comparable to those seen with gastrectomy and gastric carcinoma. Thus, the most marked changes were observed following surgical procedures involving increased enterogastric reflux and these findings lend further support to the possible involvement of N-nitroso compounds in the development of gastric cancer following both Billroth I and II gastrectomy and vagotomy with pyloroplasty.

Carcinoma↗
PubMed2002

Effects of vitamins C and E on cytotoxicity induced by N-nitroso compounds, N-nitrosomorpholine and N-methyl-N'-nitro-N-nitrosoguanidine in Caco-2 and V79 cell lines.

Since N-nitroso compounds as strong carcinogens are closely related to food and nutrition, the cytotoxic effects of N-nitrosomorpholine (NMOR) and N-methyl-N'-nitro-N-nitrosoguanidine (MNNG) and their reduction by vitamins C and E were investigated in hamster V79 cells and human colon carcinoma Caco-2 cells. Cytotoxicity was evaluated by the trypan blue exclusion technique in Caco-2 cells and by the plating efficiency assay in V79 cells. NMOR caused a dose-dependent decline of viable cells in both cell lines; MNNG induced a dose-dependent cytotoxic effect only in V79 cells. Pretreatment of cells with vitamin C and vitamin E significantly reduced the cytotoxicity of NMOR, however, both vitamins had not effect on cytotoxicity induced by MNNG. These results suggest that different N-nitroso compounds react differently with cellular macromolecules. Measurement of the level of NMOR-induced DNA strand breaks and alkali-labile sites in both cell types using the alkaline comet assay also indicates a protective effect of both vitamins against the genotoxic effects of NMOR.

Animals↗
PubMed1996

N-nitroso compounds in the gastric juice of normal controls, patients with partial gastrectomies, and gastric cancer patients.

BACKGROUND: It has been suggested that the variation of biochemical and microbiological parameters in the gastric juice may play a role in the development of gastric cancer. In the present study we concurrently assessed the presence of N-Nitroso compounds (NOC) and their precursors, bacteria and carcinoembryonic antigen (CEA) in the gastric juice of normal controls, patients with gastric resection, and advanced gastric cancer. METHODS: Detailed analyses of biochemical and microbiological parameters such as pH, nitrite (NO2) concentration, N-nitroso compounds (NOC) concentration, carcino-embryonic antigen (CEA) level, total viable counts (TVC), nitrate-reductase positive bacterial counts (NRPBC), and identification of micro-organisms were carried out. RESULTS: Significantly higher mean pH values, NO2, NOC and CEA concentrations, TVC, and NRPBC were found in partial gastrectomies compared with normal controls, and all these intragastric parameters were significantly higher in patients with gastric cancer than in those with partial gastrectomies. As far as surgical methods are concerned, higher mean pH values, NO2 and NOC concentrations, TVC, NRPBC, and anaerobic bacterial counts were observed in the juice of patients with Billroth II compared with Billroth I gastrectomies. Apart from the type of surgical reconstruction, higher mean NOC levels were recorded in patients with more severe histological changes and H. pylori infection. CONCLUSIONS: All these data suggest that the presence of high levels of NOC in the gastric juice of gastroresected patients can be considered a risk factor of gastric stump cancer.

Adult↗
PubMed1980

The reaction of N-nitroso compounds with 2,4-bis (4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide. New aspects of the destruction of the N-nitroso function.

In connection with work on 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (I), used for thiation of carbonyl compounds, different kinds of compounds with semipolar bondings have been reacted with I, especially C- and N-nitroso compounds. C-Nitroso compounds give azoxy and azo compounds. N-Nitroso compounds give new phosphorus ring systems, depending on the starting material, and the N-nitroso function is destroyed. An elimination of HNO has been observed where there was resonance stabilization in the imine formed.

Chemical Phenomena↗
PubMed1983

Presence of 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid, a precursor of a mutagenic nitroso compound, in soy sauce.

After treatment with nitrite, Japanese soy sauce was strongly mutagenic to Salmonella typhimurium TA100 without S9 mixture. Two precursors of the mutagen were isolated from Japanese soy sauce, and these were identified as (-)-(1S,3S)-1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid [(-)-(1S,3S)-MTCA] and its stereoisomer (-)-(1R,3S)-MTCA. After treatment with nitrite, 1-mg samples of these compounds induced 17,400 and 13,000 revertants of TA100, respectively, without S9 mixture. Quantitative analysis of various kinds of soy sauces produced in Japan showed the presence of 82-678 micrograms of MTCA per ml. The mutagenicities of these compounds with nitrite accounted for 16-61% of the total mutagenicity of soy sauce with nitrite. Most soy sauces produced in the United States were less mutagenic than those produced in Japan and little, if any, of these two precursors of the mutagen was found in them. A major reaction product of (-)-(1S,3S)-MTCA and nitrite was a compound having a nitroso substitution at position N-2, but this compound was not mutagenic. Thus, the mutagen(s) formed from (-)-(1S,3S)-MTCA and nitrite was a minor product(s), and its specific mutagenic activity must be very high.

Biotransformation↗
PubMed1988

[Effect of different doses of ascorbic acid on the induction of tumors with N-nitroso compound precursors in mice].

Experiments used 409 male CBA mice to study the effect of ascorbic acid on carcinogenesis induced by treatment with such precursors of nitroso compounds as sodium nitrite and morpholine. The former was given with feed in a total dose of 573-891 mg/animal and the latter--with drinking water in a total dose of 138-183 mg/animal. As a result, the total number of tumor-bearers grew from 63.8% (controls) to 82.5%. Treatment with all doses of ascorbic acid tested (1.5; 0.25 and 0.025% with drinking water) was followed by reduction in frequency of tumors in animals treated with nitroso compound precursors to 37.9, 55.1 and 60%, respectively.

Animals↗
PubMedDate not supplied

Modifications in the carcinogen-metabolizing capacity of mouse liver treated with N-nitroso compounds.

One tenth of the LD50 as a single dose of various N-nitroso compounds (N-nitrosodimethylamine; NDMA, N-nitrosodiethylamine; NDEA, N-nitrosoethylpropylamine; NEPA, N-nitrosodipropylamine; NDPA, N-nitrosomethylethylamine; NMEA, N-nitroso-methylbutylamine; NMBA and N-nitrosoethylbutylamine; NEBA) was administrated into male mice. This dose markedly increased the hepatic contents of cytochrome P450 and cytochrome b5 and activities of NADPH-cytochrome c reductase and aryl hydrocarbon hydroxylase (AHH). The highest increase in the activity of cytochrome P450 (+142% relative to the control value) was shown in animals treated with either N-nitrosoethylpropylamine or N-nitrosodiethylamine. On the other hand, the lowest increase in the activity (+16%) was revealed in animals treated with N-nitrosodimethylamine (not significant compared to the control value). Cytochrome b5 content was increased by 190% of the control value in mice treated with N-nitrosomethylbutylamine, while N-nitrosodibutylamine induced the lowest increase (+20%). The maximum increase (+182%) in the activity of aryl hydrocarbon hydroxylase was shown in animals which received N-nitrosomethylbutylamine, while the lowest increase (+23%) in animals which received N-nitrosodiethylamine. The activity of hepatic AHH was also increased above the control value in animals treated with NDMA, NEBA NDPA, NMEA and NDBA by 138, 98, 90, 89 and 69%, respectively. Identically, NADPH-cytochrome c reductase activity was increased in animals which received NEPA, NMBA, NDMA, NMEA, NDPA, NEBA and NDEA by 202, 150, 110, 95, 94, 77 and 37%, respectively.

Animals↗
PubMed1987

Dose-response curves for liver DNA fragmentation induced in rats by sixteen N-nitroso compounds as measured by viscometric and alkaline elution analyses.

A new viscometric technique, capable of detecting DNA strand breaks and alkali-labile sites by monitoring time-dependent changes of DNA-reduced viscosity, has been used to analyze dose-response curves for the induction of DNA damage in liver of rats treated with single p.o. doses of sixteen N-nitroso compounds. Statistically significant changes of DNA viscometric parameters, which are considered indicative of DNA fragmentation, were produced by N-nitrosodimethylamine (0.022 mg/kg), N-nitrosomethylethylamine (0.025 mg/kg), N-nitrosodiethylamine (0.067 mg/kg), N-nitrosodiethanolamine (1.03 mg/kg), N-nitrosodi-n-propylamine (0.31 mg/kg), N-nitrosodi-n-butylamine (0.083 mg/kg), N-nitroso-N-methylurea (0.56 mg/kg), N-nitroso-N-ethylurea (0.37 mg/kg), N-nitroso-N-butylurea (0.16 mg/kg), streptozotocin (20 mg/kg), N-nitrosomorpholine (0.4 mg/kg), N-nitrosopiperidine (2.22 mg/kg), N-nitrosopyrrolidine (5.0 mg/kg), 1-nitroso-2-imidazolidinone (0.31 mg/kg), and N-methyl-N'-nitro-N-nitrosoguanidine (5.57 mg/kg). The contemporary measurement of liver DNA fragmentation by the alkaline elution technique revealed that in our experimental conditions higher doses are needed to produce a statistically significant increase of DNA elution rate. This suggests that the viscometric method is capable of detecting smaller levels of N-nitroso compound-induced DNA fragmentation, but it does not exclude that the sensitivity of alkaline elution can be improved by appropriate modifications of the experimental procedure. With both techniques DNA damage was undetectable in liver of rats treated with 540 mg/kg of the non-hepatocarcinogen N-nitrosodiphenylamine. With the exception of N-nitrosodiethanolamine, that exhibited a plateau effect, all the other N-nitroso compounds examined displayed a linear dose-response curve over the entire wide range of doses tested. Consequently, a nonlinearity of the relationship between dose and tumor response cannot be attributed to a nonlinearity of the pharmacokinetic processes involved in the formation of DNA damage.

Animals↗
PubMed2005

A review: dietary and endogenously formed N-nitroso compounds and risk of childhood brain tumors.

Maternal dietary exposure to N-nitroso compounds (NOC) or to their precursors during pregnancy has been associated with risk of childhood brain tumors. Cured meat is one source of exposure to dietary NOC and their precursors. Most epidemiological studies that have examined the role of maternal consumption of cured meats during pregnancy have found a significant positive association between maternal intake of cured meat and the risk of childhood brain tumor (CBT). NOC consist of two main groups, N-nitrosamines and N-nitrosamides. The carcinogenicity profiles of NOC suggest that N-nitrosamides rather than N-nitrosamines are the compounds that may be associated with CBT and that they should be investigated more closely in epidemiological studies. We present a review of the chemical and carcinogenic properties of NOC in connection with the findings of case-control studies. This approach may be helpful in determining the essential information that must be collected in future epidemiological studies on CBT.

Brain Neoplasms↗
PubMed1982

Total nitroso compounds in gastric juice.

A method is described for the measurement of 'total nitroso compounds' in gastric juice. It is applicable to small samples and in the presence of food. The method depends on treatment with hydrazine sulfate at pH 4 to destroy nitrite, decomposition by addition of the sample to HBr/acetic acid in boiling ethyl acetate and determination of the nitric oxide evolved by a chemiluminescence analyser. The method is being applied to a study of samples from healthy subjects throughout 24 hours of normal diet, prior to similar studies with patients.

Diet↗
PubMed1983

The formation of nitrite and N-nitroso compounds in salivas in vitro and in vivo.

The considerable differences in salivary nitrite levels observed previously in subjects who had abstained overnight from dietary nitrate as completely as possible were again found in tests on ten separate days. A 25-fold variation was observed in the rate of production of nitrite in vitro during the incubation of salivas from different subjects with 16 mM-nitrate under standardized conditions. N-Nitroso compounds were detected as a group on 11/100 and 14/100 occasions after incubations in vitro without and with added nitrate, respectively. No significant changes in salivary nitrite level were found 1 hr after the volunteers had ingested water-borne nitrate at approximately the World Health Organization recommended limit for continuous use (50 mg NO-3/litre), but increases in nitrite concentration were consistently found after volunteers ingested nitrate in water at four times this concentration. Although the nitrite concentrations were markedly increased following the intake of nitrate at the higher level, the occurrence of N-nitroso compounds in the salivas of the volunteers was greater immediately prior to the ingestion of water-borne nitrate than 1 hr afterwards.

Female↗
PubMed1996

DNA damage induced by seven N-nitroso compounds in primary cultures of human and rat kidney cells.

Seven N-nitroso compounds (NOC), known to induce kidney tumors in rats, were assayed for DNA-damaging activity in primary cultures of human and rat kidney cells. DNA fragmentation was measured by the alkaline elution technique. Positive responses were obtained in cells of both species with N-nitrosodimethylamine (32 mM), N-nitrosodiethylamine (32 mM), N-nitrosodi-n-propylamine (10 mM), N-ethyl-N-hydroxyethylnitrosamine (18 mM), and streptozotocin (1 mM). N-nitrosodiethanolamine and N-nitrosomorpholine were inactive at the highest concentration tested (32 mM). The responses of human kidney cells were qualitatively similar to those of rat kidney cells, but statistically significant differences between the two species in the DNA-damaging potencies were observed with N-ethyl-N-hydroxyethylnitrosamine and streptozotocin, both more genotoxic in rat cells. Taken as a whole, the results suggest on the one hand that the five active NOC might be carcinogenic for the kidney in humans, and on the other hand that the rat kidney cell/DNA damage assay is a valid model for predicting the genotoxic potential of NOC in human kidney cells.

Animals↗
PubMed2006

Partial purification from hot dogs of N-nitroso compound precursors and their mutagenicity after nitrosation.

Hot dogs contain apparent N-nitroso compounds (ANC) and ANC precursors (ANCP). ANCP purification was followed by nitrosation, sulfamic acid treatment, and analysis for ANC. Aqueous hot dog extracts were adsorbed on silica gel, which was eluted with MeCN and MeOH. The MeOH eluate was adsorbed on cation exchange resin (H+ form) and eluted with NH4OH. Eluted ANCP traveled at moderate speeds in high-performance liquid chromatography (HPLC) on amino and Pb2+ columns. Gas chromatography-mass spectrometry (GC-MS) of trimethylsilyl (TMS) derivatives of crude water extract indicated the presence of glycerol, phosphate, lactic acid, and two monosaccharides. GC-MS of TMS derivatives of Pb2+ column HPLC eluates indicated that ANCP included 1-deoxy-N-1-glucosyl glycine. The nitrosated NH4OH eluate showed 4x background mutagenic activity for Salmonella typhimurium TA-100. Un-nitrosated fractions showed 2x background activity. Although tryptophan nitrosation gave 88% ANC yield, tryptophan is probably not a major ANCP in hot dogs. Hot dog patties prepared with or without sucrose or glucose showed similar ANC and ANCP levels. We discuss possible implications of these findings for the etiology of colon cancer.

Amino Acids↗
PubMed1990

Detoxifying potential of thioproline against N-nitroso compounds, N-nitrosodimethylamine and N-nitrosocimetidine.

Thioproline (TPRO), an effective nitrite trapping agent in vivo, was examined for its detoxifying ability in rats against N-nitrosodimethylamine (NDMA) and N-nitrosocimetidine (NCIM). When NDMA (37-101.5 mg/kg) was administered with TPRO (532 mg/kg), no influence of TPRO on NDMA-induced lethality and histological results in liver were observed. NDMA oxygenase activity measured by formaldehyde formation was not affected either. Denitrosation is a route of detoxication of N-nitroso compounds. When NCIM (100 mg/kg), a direct acting mutagen but not carcinogen, was given by gavage with TPRO, urinary excretion of N-nitrosothioproline (NTPRO) in rats apparently increased compared with TPRO alone. This result shows that TPRO is a trapping agent in vivo for nitrosating (NO) species originating from N-nitroso compounds, e.g., NCIM, which are denitrosated non-enzymatically in stomach acidic conditions. Transnitrosation from NDMA to TPRO, where enzymatic denitrosation is required, did not occur in measurable amount after oral administration of NDMA and TPRO.

Animals↗
PubMed1982

N-Nitroso compounds and childhood brain tumors: a case-control study.

We questioned mothers of 209 young brain tumor patients and mothers of 209 controls about experiences of possible etiological relevance which they had during pregnancy or which their children had while growing up. Long-suspected brain tumor risk factors such as head trauma and X-rays appeared to be factors for relatively few cases. Increased risk was associated with maternal contact with nitrosamine-containing substances such as burning incense (odds ratio, 3.3; p = 0.005), sidestream cigarette smoke (odds ratio, 1.5; p = 0.03), and face makeup (odds ratio, 1.6; p = 0.02); with maternal use of diuretics (odds ratio, 2.0; p = 0.03) and antihistamines (odds ratio, 3.4; p = 0.002); and with the level of maternal consumption of cured meats (p = 0.008). These drugs contain nitrosatable amines and amides, and the cured meats contain nitrites, chemicals which are precursors of N-nitroso compounds. We propose a hypothesis that brain tumors in these young people are related to in utero exposure to N-nitroso compounds and their precursors, the most potent nervous system carcinogens known in experimental animals.

Adolescent↗