PMID: 11342234May 9, 2001Paper

Halogenated 2,5-pyrrolidinediones: synthesis, bacterial mutagenicity in Ames tester strain TA-100 and semi-empirical molecular orbital calculations

Mutation Research
B A FreemanW F Haddon

Abstract

The chloroimide 3,3-dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione, a tetrachloroitaconimide, is the principal mutagen produced by chlorination of simulated poultry chiller water. It is the second most potent mutagenic disinfection by-product of chlorination ever reported. Six of seven new synthetic analogs of this compound are direct-acting mutagens in Ames tester strain TA-100. Computed energies of the lowest unoccupied molecular orbital (E(LUMO)) and of the radical anion stability (DeltaH(f)(rad)-DeltaH(f)) from MNDO-PM3 for the chloroimides show a quantitative correlation with the Ames TA-100 bacterial mutagenicity values. The molar mutagenicities of these direct acting mutagenic imides having an exocyclic double bond fit the same linear correlation (lnM(m) vs. E(LUMO); lnM(m) vs. DeltaH(f)(rad)--DeltaH(f)) as the chlorinated 2(5H)-furanones, including the potent mutagen MX, 3-chloro-4-(dichloro-methyl)-5-hydroxy-2(5H)-furanone, a by-product of water chlorination and paper bleaching with chlorine. Mutagenicity data for related haloimides having endocyclic double bonds are also given. For the same number of chlorine atoms, the imides with endocyclic double bonds have significantly higher Ames mutagenicity compared to th...Continue Reading

References

Sep 1, 1986·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·M S Masri
May 1, 1983·Mutation Research·D M Maron, B N Ames
Feb 1, 1997·Chemical Research in Toxicology·R T LaLonde, F Ramdayal
Jun 18, 1997·Journal of the National Cancer Institute·R L MelnickV Dellarco
Jun 18, 1997·Journal of the National Cancer Institute·H KomulainenJ Tuomisto

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Citations

Dec 13, 2016·Environmental Science & Technology·Maolida NihemaitiJean-Philippe Croué
Mar 16, 2018·The Journal of Toxicological Sciences·Yu HaranosonoHideyuki Sakaki
Oct 20, 2020·Chemical Communications : Chem Comm·Piers A Townsend, Matthew N Grayson

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