Structure-mutagenicity relationships of 5-nitro-2-furylethylenes in Salmonella typhimurium TA98

Šturdı́k, Ernest; Rosenberg, Michael; Štibrányi, Ladislav; Baláž, Štefan; Chreno, O.; Ebringer, L.; Ilavsky, D.; Végh, Dániel

doi:10.1016/s0009-2797(85)80092-2

Cited by 20 publications

(2 citation statements)

References 14 publications

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“…Thus, 2-furylethylene derivatives with the nitro group coupled outside the furan ring appear to be lower genotoxic agents when compared with the 5-nitrofurans. This would agree with several experimental data showing that only those derivatives with the nitro group in position 5 of the furan ring are mutagenic and the substitution of this functional group leads to the loss of mutagenic activity (3,24,25).…”

Section: Discussionsupporting

confidence: 92%

Comparative genotoxic evaluation of 2-furylethylenes and 5-nitrofurans by using the comet assay in TK6 cells

et al. 2005

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The genotoxicity of three 2-furylethylene derivatives and four 5-nitrofurans was evaluated by using the comet assay in human lymphoblastoid cultured TK6 cells. The 2-furylethylene derivatives were 2-furyl-1-nitroethene, 1-(5-bromofur-2-yl)-2-nitroethene and 1-(5-bromofur-2-yl)-2-bromo-2-nitroethene, while the 5-nitrofurans were nitrofurantoin, nitrofurazone, furazolidone and 5-nitro-2-furanacrolein. The treatments lasted for 3 h in the absence of metabolic activation. No genotoxic effects were observed for two of the 2-furylethylene compounds, while the derivative 1-(5-bromofur-2-yl)-2-nitroethene showed a statistically significant response mainly at the highest concentration tested; this effect was considered biologically relevant and the compound was classified as slightly genotoxic. On the other hand, for the classical 5-nitrofurans tested there is a tendency towards a dose-related increase of the DNA damage in the comet assay and the observed increases for the parameters analysed (Olive tail moment, tail % DNA and tail length) were significant for all compounds. Then, the four 5-nitrofurans tested were considered genotoxic. These results show that the position of the nitro group influences the genotoxicity of the assayed compounds. Thus, in this comet assay, the 2-furylethylene derivatives having the nitro group attached outside the furan ring appear to be much less genotoxic than the 5-nitrofurans.

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Section: Discussionsupporting

confidence: 92%

Comparative genotoxic evaluation of 2-furylethylenes and 5-nitrofurans by using the comet assay in TK6 cells

et al. 2005

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“…5-Nitro-2-furylacrylic acid (NFAA) (1) was obtained from Slovakofarma Hlohovec (Czechoslovakia). Alkyl esters and amides of NFAA (2)(3)(4)(5)(6)(7)(8)(9) were synthesized according to Sturdik et al (13,14). Nitrovin (9) was obtained from Chemapol Praha (Czechoslovakia), and nitrofurantoin (10) (o-Nitrophenyl)-/3-D-galactopyranoslde (ONPG) and p -nltrophenyl phosphate (PNPP) are the substrates for determination of the enzymes -galactosldase and alkaline phosphatase, respectively.…”

Section: Methodsmentioning

confidence: 99%

Use of specific bacteria for the determination of mutagenic and carcinogenic compounds

Miertus¹,

Šturdı́k²,

Vojteková³

1987

Anal. Chem.

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Possibilities of the use of Escherichia coll K-12 In the determination of mutagenic compounds have been tested. Analytical parameters, e.g., the range of linearity of the analytical curve, the detection limit and the sensitivity, the accuracy, and the precision of analysis, have been evaluated for a series of nitrofurans. The detection limit Is In the range of 10~7-10~* mol L~\ Analyses of real samples (determination of 5-nHro-2-furylacryllc acid In wine and nitrovin In chicken meat) have been completed without any preseparation.

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SOS chromotest results in a broader context: Empirical relationships between genotoxic potency, mutagenic potency, and carcinogenic potency

White

Rasmussen

1996

Environ. Mol. Mutagen.

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Structure-mutagenicity relationships of 5-nitro-2-furylethylenes in Salmonella typhimurium TA98

Cited by 20 publications

References 14 publications

Comparative genotoxic evaluation of 2-furylethylenes and 5-nitrofurans by using the comet assay in TK6 cells

Comparative genotoxic evaluation of 2-furylethylenes and 5-nitrofurans by using the comet assay in TK6 cells

Use of specific bacteria for the determination of mutagenic and carcinogenic compounds

SOS chromotest results in a broader context: Empirical relationships between genotoxic potency, mutagenic potency, and carcinogenic potency

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