Disease relevance of N-NITROSOPYRROLIDINE

• N-Nitrosopyrrolidine induced hepatocellular carcinomas in 20 of 23 rats, liver neoplastic nodules in 16 of 23 rats, and altered liver cell foci in 23 of 23 rats [1].
• The in vitro genotoxicity of N-nitrosopyrrolidine (NPy) has been studied in Salmonella typhimurium strain TA1535 in the presence of untreated and pyrazole-, phenobarbital (PB)-, 4-day ethanol (EtOH)-, 10-day EtOH- and 3-methylcholanthrene (3-MC)-pretreated male Sprague-Dawley rat liver S-9 fractions [2].
• The cytotoxic and mutagenic effects of increasing concentrations of N-nitrosopyrrolidine (NPYR) were studied using various DNA repair mutants of Escherichia coli together with rat-liver S9 activation system [3].
• Induced mutations in M13mp2 phage DNA exposed to N-nitrosopyrrolidine with UVA irradiation [4].
• N-Nitrosopyrrolidine (0.02%) did not affect the incidence or number of PN hyperplasias but increased those of papillomas [5].

High impact information on N-NITROSOPYRROLIDINE

• The liver S9 and hepatocyte preparations from hamsters were consistently more effective than were preparations from rats in metabolizing nitrosodimethylamine (NDM), nitrosodiethylamine, nitrosodiallylamine, nitrosopyrrolidine (NP), nitrosomorpholine (NM), nitrosodiethylmethylurea (NDEMU), and nitrosodimethyl-ethylurea (NDMEU) to mutagenic forms [6].
• Nitroso-3-pyrrolidinol was mutagenic in the absence of microsomes, thereby suggesting a role of hydroxylation in the metabolic activation of nitrosopyrrolidine to an ultimate carcinogenic species [7].
• The carcinogens nitrosopiperidine and nitrosopyrrolidine required metabolic activation before manifesting mutagenic activity [7].
• N-Nitrosamines [N-nitrosodimethylamine (DMN), N-nitrosodiethylamine (DEN), N,N'-dinitrosopiperazine (DNP), N-nitrosopyrrolidine (NPy), and N-nitrosopiperidine (NPd)] labeled with 14C were each then added at 100 mumoles for 24 hours [8].
• Neutral thermal hydrolysates of hepatic DNA isolated from rats treated with N-nitrosopyrrolidine contained a fluorescent adduct, as previously reported (E.J. Hunt and R.C. Shank, Biochem. Biophys. Res. Commun., 104: 1343, 1982) [9].

Chemical compound and disease context of N-NITROSOPYRROLIDINE

• The mutagenicity of some N-nitrosodialkylamines, i.e. N-nitrosodimethylamine, N-nitrosodiethylamine, N-nitrosodi-n-butylamine, N-nitrosomorpholine and N-nitrosopyrrolidine, was assayed on Salmonella typhimurium TA100 by the pre-incubation method, and the effect of changing the pH of the pre-incubation mixture was examined [10].
• Mutagenesis induced by the N-nitroso compounds: N-nitrosomethylurea, N-nitrosoethylurea, N-nitrosodi-n-propylamine and N-nitrosopyrrolidine was measured in Salmonella typhimurium TA100, TA102 and TA104 [11].

Biological context of N-NITROSOPYRROLIDINE

• The role of DNA-repair processes in N-nitrosopyrrolidine-induced mutagenesis [3].
• Following incubation with various concentrations of the nitrosamines dimethylnitrosamine, N-nitrosopyrrolidine and 1-nitrospiperidine, all of which are bioactivated by CYP2E1, cytotoxicity and DNA damage were assessed using either the neutral red assay or comet assay respectively [12].
• N-nitrosopyrrolidine (NPYR) is an important carcinogen, frequently present in the environment and food chain [13].
• N-Nitrosodimethylamine, N-nitrosodiethylamine, N-nitrosopyrrolidine, N-nitrosonornicotine and N- nitrosohydroxyproline were detected in the saliva from the tobacco chewers . These N-nitroso compounds are probably leached from the tobacco itself and/or are formed in situ by the nitrosation of tobacco alkaloids as well as that of secondary amines [14].
• 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 [15].

Anatomical context of N-NITROSOPYRROLIDINE

• Metabolism of the liver carcinogen N-nitrosopyrrolidine by rat liver microsomes [16].
• Binding of metabolites of N-nitrosopyrrolidine to DNA was detected only in rat esophagus [17].
• N-Nitrosopyrrolidine was oxidized in both the alpha-and beta-position by all three cell lines, the oxidation at the alpha-position being predominant [18].
• Evidence is presented that the likely major amine precursors to N-nitrosopyrrolidine in cooked bacon are free proline in the adipose tissue and to a lesser extent, collagenous connective tissues [19].
• In vitro metabolism of N-nitrosopyrrolidine by rat lung subcellular fractions: alpha-hydroxylation in a non-target tissue [20].

Associations of N-NITROSOPYRROLIDINE with other chemical compounds

• The metabolism of several N-nitrosamines (N-nitrosodimethylamine, N-nitrosoethylmethylamine, N-nitrosodiethylamine, N-nitrosobenzylmethylamine, and N-nitrosopyrrolidine) in cultured human and rat esophagus has been investigated by measuring (a) CO2, (b) metabolites with an oxo group, and (c) metabolites bound to DNA [17].
• Differential effect of chronic ethanol consumption on the carcinogenicity of N-nitrosopyrrolidine and N'-nitrosonornicotine in male Syrian golden hamsters [21].
• N-Nitrosopiperidine (NPIP; 0.6 microgram/day) and N-nitrosopyrrolidine (NPYR; 0.4 microgram/day) were also present in one sample [22].
• The effect of pyrazole, phenobarbital, ethanol and 3-methylcholanthrene pretreatment on the in vivo and in vitro genotoxicity of N-nitrosopyrrolidine [2].
• The metabolism of N-nitrosopyrrolidine (NPYR) to 4-hydroxybutanal (4-HB) (the first stable product of the putative alpha-hydroxylation pathway) and its bioactivation in the Ames bacterial mutagenicity test system were examined in the presence of a number of inhibitors [23].

Gene context of N-NITROSOPYRROLIDINE

• Binding levels of DNP were as high as those with the two acyclic N-nitrosamines DMN and DEN, but binding levels of NPy and NPd were lower [8].
• The in vitro alpha-hydroxylation of N-nitrosopyrrolidine (NPYR) by both isolated rabbit liver microsomes and purified cytochrome P-450 isozymes was investigated [24].
• N-Nitrosopyrrolidine induced hepatocellular tumors in 26 of 29 animals and induced 1 olfactory carcinoma [25].
• NPYR and NPIP were also occasionally detected in several vegetables fermented in brine collected in Tunisia and China. The possible role of nitrosamines in the etiology of NPC is discussed [26].
• Cytochrome P450 2A-catalyzed metabolic activation of structurally similar carcinogenic nitrosamines: N'-nitrosonornicotine enantiomers, N-nitrosopiperidine, and N-nitrosopyrrolidine [27].

Analytical, diagnostic and therapeutic context of N-NITROSOPYRROLIDINE

• The same product was isolated as its dinitrophenylhydrazone derivative after incubation of rat liver microsomes with nitrosopyrrolidine and after treatment of rats with nitrosopyrrolidine [28].
• Incubation mixtures of N-nitrosopyrrolidine, cofactors, and hepatic microsomes from Aroclor pretreated or control F344 rats were derivatized with (2,4-dinitrophenyl)hydrazine reagent and the resulting mixtures analyzed by high-performance liquid chromatography [29].
• Comparison of liver tumor frequencies after intermittent oral administration of different doses of N-nitrosopyrrolidine in Sprague-Dawley rats [30].
• Whole-body autoradiography performed with hemisections of mice at -80 degrees C (to prevent evaporation of the volatile N-nitrosopyrrolidine) and with dry tape-sections (to localize the non-volatile metabolites), using pretreated and non-pretreated mice, indicated a uniform distribution of the non-metabolized N-nitrosopyrrolidine in the tissues [31].
• Analysis of volatile N-nitrosamines using gas chromatography with Coulson detector:estimation of N-nitrosopyrrolidine by thin-layer chromatography with fluorimetric detection [32].

References