Genotoxic activities of 2-nitronaphthofurans and related molecules

Arnaise, Sylvie; Bœuf, Hélène; Buisson, Jean‐Pierre; Cantat, N.; Demerseman, P.; Einhorn, Jacques; Lamotte, G.; Lemelin, M.; Brimer, Patricia A.; Perdue, S.W.; Hsie, Abraham W.; Royer, R.; Kelly, Frank J.; Hofnung, Maurice

doi:10.1093/mutage/1.3.217

Cited by 48 publications

(15 citation statements)

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“…The AIA and amino-carboline data sets will be discussed separately. An empirical discussion of ring system and ring substitution effects on mutagenic potency in a congeneric series of benzo-and naphthofurans has been presented by Arnaise et al [1986] (see especially Fig. 4 therein).…”

Section: Structural Parameters As Determinants Of Mutagenic Potencymentioning

confidence: 99%

Quantitative structure‐activity relationships of heterocyclic amine mutagens formed during the cooking of food

Hatch

Knize

Felton

1991

Environ and Mol Mutagen

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The major protein-rich foods, particularly muscle meats, contain part-per-billion quantities of potent mutagens formed by frying or broiling to a well-done state. Related mutagens are formed by pyrolysis of amino acids or proteins and in heated model systems. The thermic mutagens so far identified are heterocyclic aromatic amines of aminoimidazo-azaarene (AIA) and aminocarboline classes. The chemicals require activation by enzymes to form metabolites reactive with nucleic acids. These thermic mutagens, and numerous synthetic congeners, exhibit an enormous range of potency as frameshift mutagens in the Ames/Salmonella assay. However, structural variations are nominal within the two classes. Structural parameters that appeared relevant to determining potency were selected for 38 AIAs and 23 amino-carbolines. For the AIA class these were: the number of fused rings, the number of heteroatoms in Rings 2 and 3, methyl substitution on imidazo ring nitrogen atoms, and methyl substitution on ring carbon atoms. For the amino-carboline class the structural parameters were: the position of the pyridine-type nitrogen atom in Ring 1, the substitution position of the exocyclic amino group on Ring 1, and methyl substitution on ring carbon atoms. These structural parameters may influence mutagenic potency in the following ways. 1) Electronic or steric effects may determine the reactivity and stability of the ultimate mutagenic metabolite. Optimal balance of reactivity and lifetime of this transient intermediate may be required for access to and reaction with nuclear DNA to cause mutations. 2) Substitution on the rings may block detoxication reactions. The structural parameters identified should prove useful in predicting the mutagenicity of untested compounds of these types.

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Section: Structural Parameters As Determinants Of Mutagenic Potencymentioning

confidence: 99%

Quantitative structure‐activity relationships of heterocyclic amine mutagens formed during the cooking of food

Hatch

Knize

Felton

1991

Environ and Mol Mutagen

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“…Addition of one or more rings to the nitrofuran results in increased genotoxicity [156]. For instance, the nitro-2-naphthofuran derivative 7-methoxy-2-nitronaphtho[2,1-b]furan (figure 24) ranks among the most potent mutagens known in bacteria [157].…”

Section: Nitro Substituent On Furan Ring and Structural Modificationsmentioning

confidence: 99%

Influence of structural and functional modifications of selected genotoxic carcinogens on metabolism and mutagenicity – a review

Kulkarni

Moir

Zhu

2007

SAR and QSAR in Environmental Research

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Alterations in molecular structure are responsible for the differential biological response(s) of a chemical inside a biosystem. Structural and functional parameters that govern a chemical's metabolic course and determine its ultimate outcome in terms of mutagenic/carcinogenic potential are extensively reviewed here. A large number of environmentally-significant organic chemicals are addressed under one or more broadly classified groups each representing one or more characteristic structural feature. Numerous examples are cited to illustrate the influence of key structural and functional parameters on the metabolism and DNA adduction properties of different chemicals. It is hoped that, in the event of limited experimental data on a chemical's bioactivity, such knowledge of the likely roles played by key molecular features should provide preliminary information regarding its bioactivation, detoxification and/or mutagenic potential and aid the process of screening and prioritising chemicals for further testing.

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“…The overlap between the Ames and SOS Chromotest for these chemicals was 93%. Arnaise et al (1986) evaluated sixty 2-nitrofuran derivatives in the SOS Chromotest. Fifty-one gave positive responses.…”

Section: Introductionmentioning

confidence: 99%

Genotoxicity of 22 pesticides in microtitration SOS chromotest

Schurr

1990

Environ. Toxicol. Water Qual.

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The authors adapted microtitration techniques to the SOS Chromotest, and thereby established a simple and reliable modified genotoxicity test: the Microtitration SOS Chromotest. This test employs microtitration techniques and photometric analysis with numerical readout. These data are integrated into the computerized data processing program Statistical Analysis System to obtain genotoxicity and toxicity results of a chemical or chemical mixture within 16 h. In order to test the applicability of the new system, the genotoxicity and toxicity of 22 pesticides were studied. A two‐sample t test was employed to determine the level of significance (p < 0.05). Nine of the pesticides were found to induce the SOS response in Escherichia coli cells. Their relative degrees of induction based on SOS inducing potency values are as follows: captafol > captan > folpet > dinoseb > ferbam > linuron > alachlor > phosmet > cacodylic acid. The addition of rat liver S9 mix does not transform the nongenotoxic pesticides tested into genotoxic forms but significantly decreases the inducing ability of most positive pesticides. The Microtitration SOS Chromotest is rapid and efficient in providing evidence for decision‐making related to cleanup of chemical spills and discharges where time is a critical factor. This method maintains its high accuracy and sensitivity compared with conventionally used assays. The studies of pesticide genotoxicity using this test confirm the applicability, reliability, and sensitivity of the Microtitration SOS Chromotest as a simple, efficient, and rapid genotoxicity prescreening system as well as an excellent research tool for genotoxic mechanism studies.

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Genotoxic activities of 2-nitronaphthofurans and related molecules

Cited by 48 publications

References 0 publications

Quantitative structure‐activity relationships of heterocyclic amine mutagens formed during the cooking of food

Quantitative structure‐activity relationships of heterocyclic amine mutagens formed during the cooking of food

Influence of structural and functional modifications of selected genotoxic carcinogens on metabolism and mutagenicity – a review

Genotoxicity of 22 pesticides in microtitration SOS chromotest

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