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Analysis of DNA adducts formed in vivo in rats and mice from 1,2-dibromoethane, 1,2-dichloroethane, dibromomethane, and dichloromethane using HPLC/accelerator mass spectrometry and relevance to risk estimates.
Chem Res Toxicol
November 2007
Department of Biochemistry and Center in Molecular Toxicology, Vanderbilt University School of Medicine, Nashville, Tennessee 37232, USA.
Dihaloalkanes are of toxicological interest because of their high-volume use in industry and their abilities to cause tumors in rodents, particularly dichloromethane and 1,2-dichloroethane. The brominated analogues are not used as extensively but are known to produce more toxicity in some systems. Rats and mice were treated i.
View Article and Find Full Text PDFChemical toxicology of reactive intermediates formed by the glutathione-dependent bioactivation of halogen-containing compounds.
Chem Res Toxicol
January 2008
Department of Pharmacology and Physiology, University of Rochester Medical Center, Rochester, New York 214642, USA.
The concept that reactive intermediate formation during the biotransformation of drugs and chemicals is an important bioactivation mechanism was proposed in the 1970s and is now accepted as a major mechanism for xenobiotic-induced toxicity. The enzymology of reactive intermediate formation as well as the characterization of the formation and fate of reactive intermediates are now well-established. The mechanism by which reactive intermediates cause cell damage and death is, however, still poorly understood.
View Article and Find Full Text PDFLithium carbenoids-ultra-reactive yet selective reagents for methylenation and halomethylenation of sulfones.
J Org Chem
July 2006
Chemical Research and Development, 31073-091-201, Pfizer, Incorporated, 7000 Portage Road, Kalamazoo, Michigan 49001-0102, USA.
The first efficient, one-pot method for methylenation of p-toluyl sulfones (i.e., the transformation of p-MePhSO2CHR2 into R2CCH2) is described.
View Article and Find Full Text PDFMetabolism of mono- and dihalogenated C1 and C2 compounds by Xanthobacter autotrophicus growing on 1,2-dichloroethane.
Biodegradation
April 2007
Institute of Chemical Engineering, Bulgarian Academy of Sciences, Acad. G. Bonchev str., bl. 103, 113, Sofia, Bulgaria.
The conversion of and toxic effects exerted by several mono- and dihalogenated C1 and C2 compounds on cultures of Xanthobacter autotrophicus GJ10 growing on 1,2-dichloroethane were investigated. Bromochloromethane, dibromomethane and 1-bromo-2-chloroethane were utilized by strain GJ10 in batch culture as a cosubstrate and sole carbon source. The rate of degradation of dihalomethanes by whole cells was lower than that of 1,2-dichloroethane, but a significant increase of the rate of dihalomethane biodegradation was observed when methanol or ethanol were added as a cosubstrate.
View Article and Find Full Text PDFGlutathione-dependent bioactivation of haloalkanes and haloalkenes.
Drug Metab Rev
October 2004
Department of Pharmacology and Physiology, University of Rochester Medical Center, Rochester, New York 14642, USA.
Haloalkanes and haloalkenes constitute an important group of widely used chemicals that have the potential to induce toxicity and cancer. The toxicity of haloalkanes and haloalkenes may be associated with cytochromes P450- or glutathione transferase-dependent bioactivation. This review is concerned with the glutathione- and glutathione transferase-dependent bioactivation of dihalomethanes, 1,2-dihaloalkanes, and haloalkenes.
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