Heterocyclic diazo-compounds. 3. Structure and unusual properties of primary 2-nitrosoaminobenzimidazoles

Kolodyazhnaya, S. N.; Диваева, Л. Н.; Zheltikova, N. N.; Simonov, A. M.

doi:10.1007/bf00476539

Cited by 4 publications

(2 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The method, however, seems to have had limited application. [409] [408] When 1H-benzimidazole-2-nitrosamine is treated in acetonitrile solution with dry hydrochloric acid or hydrogen bromide in the presence of copper metal, the 2-chloro (71%) and 2-bromo (63%) derivatives are formed.…”

Section: 44243mentioning

confidence: 99%

Product Class 4: Benzimidazoles

Neier¹,

Bellus²

2002

Category 2, Hetarenes and Related Ring Systems

View full text Add to dashboard Cite

Section: 44243mentioning

confidence: 99%

Product Class 4: Benzimidazoles

Neier¹,

Bellus²

2002

Category 2, Hetarenes and Related Ring Systems

View full text Add to dashboard Cite

“…The N-nitroso products were found to be “yellow crystalline substances … stable on prolonged storage in the dark at 20°C.” They suggested that the compounds exist primarily as nitrosoimino tautomers (Fig. 3) [25]. 2-Amino-1-methylbenzimidazole, studied by the Rostov group, is structurally equivalent to IQ, except that the terminal aromatic ring is absent ( i.e.…”

Section: Introductionmentioning

confidence: 99%

Activation of aminoimidazole carcinogens by nitrosation: Mutagenicity and nucleotide adducts

Zenser

Lakshmi

Schut

et al. 2009

Mutation Research/Genetic Toxicology and Environmental Mutagene

View full text Add to dashboard Cite

Abstract2-Amino-3-methylimidazo[4,5-f]quinoline (IQ) and 2-amino-3,8-dimethylimidazo [4,5-f] quinoxaline (MeIQx) are heterocyclic amines (HCA) derived from high temperature cooking of meat and thought to cause colon cancer in humans. Reactive nitrogen oxygen species, which are mediators of the inflammatory response, can convert these amines to the corresponding N-nitrosamines, N-NO-IQ and N-NO-MeIQx. This study was designed to evaluate whether these N-nitrosamines are genotoxic and could be responsible, in part, for the high incidence of colon cancer in individuals with colitis. Such an association would counsel reduced intake of well-done red meat by colitis patients. Mutagenicity was evaluated by reversion of a lacZ frameshift allele in three different E. coli strains. Strains DJ701 and DJ702 express recombinant (S. typhimurium) aromatic amine N-acetyltransferase; DJ702 also expresses recombinant human cytochrome P450 1A2 and NADPH-P450 reductase; and DJ2002 served as an N-acetyltransferase-negative control. In strain DJ701, N-NO-IQ and N-NOMeIQx elicited dose-dependent mutagenicity, which was not further increased in DJ702. Neither nitrosamine was mutagenic in strain DJ2002. While both N-nitrosamines are stable for >4 hours (pH 7.4, 37°C), they react with DNA or 2′-deoxyguanosine 3′-monophosphate at lower pH (5.5) to form adducts. HOCl, a component of the inflammatory response, increased adduct formation, as measured by 32 P-postlabeling. Following treatment with nuclease P1 and separation by two-dimensional thinlayer chromatography and then HPLC, N-NO-IQ and N-NO-MeIQx were shown to form the same adducts as those formed by N-OH-MeIQx or N-OH-IQ, namely N-(deoxyguanosin-8-yl) adducts. In summary, these N-nitrosamines are genotoxic and might be alternatives to their hydroxylamine analogues as activated intermediates leading to initiation of colon cancer in individuals with colitis.

show abstract

Imidazoles

Grimmett

1996

Comprehensive Heterocyclic Chemistry II

110

View full text Add to dashboard Cite

Heterocyclic diazo-compounds. 3. Structure and unusual properties of primary 2-nitrosoaminobenzimidazoles

Cited by 4 publications

References 5 publications

Product Class 4: Benzimidazoles

Product Class 4: Benzimidazoles

Activation of aminoimidazole carcinogens by nitrosation: Mutagenicity and nucleotide adducts

Imidazoles

Contact Info

Product

Resources

About