Genetic effects of dimethyl sulfate, diethyl sulfate, and related compounds.
DMS and DES are monofunctional alkylating agents that have been shown to induce mutations, chromosomal aberrations, and other genetic alterations in a diversity of organisms. They have also been shown to be carcinogenic in animals. As an alkylating agent, DMS is a typical SN2 agent, attacking predominantly nitrogen sites in nucleic acids. DES is capable of SN1 alkylations as well as SN2 and thereby causes some alkylation on oxygen sites including the O6-position of guanine which is thought to be significant in mutagenesis by direct mispairing. The mutagenicity of DMS is better explained in terms of indirect, repair-dependent processes. With respect to both alkylating activity and genetic effects, striking similarities are found between DMS and MMS and between DES and EMS. In most systems where they have been tested, both DMS and DES are mutagenic. Results of many of the mutagenesis studies involving these compounds and other alkylating sulfuric acid esters are summarized in Tables 6, 7, 8, 9 and 10 of this review. Most data are consistent with these agents acting primarily as base-pair substitution mutagens. In the case of DES, strong specificity for G.C to A.T transitions has been reported in some systems but has not been clearly supported in some others. Low levels of frameshift mutations of the deletion type are also likely. In addition to the induction of mutations, recombinogenic and clastogenic effects have been described.
D000477:Alkylating Agents / Q000494:pharmacology* / Q000633:toxicity; D000818:Animals; D001419:Bacteria / Q000235:genetics; D002273:Carcinogens; D002478:Cells, Cultured; D002869:Chromosome Aberrations; D002875:Chromosomes / Q000187:drug effects; D000458:Cyanobacteria / Q000235:genetics; D004247:DNA / Q000378:metabolism; D004260:DNA Repair / Q000187:drug effects; D004261:DNA Replication; D004330:Drosophila / Q000235:genetics; D005399:Fishes / Q000235:genetics; D005658:Fungi / Q000235:genetics; D005799:Genes, Dominant; D007313:Insecta / Q000235:genetics; D009153:Mutagens; D009154:Mutation; D010944:Plants / Q000235:genetics; D012854:Sister Chromatid Exchange; D013463:Sulfuric Acid Esters / Q000494:pharmacology*; D013464:Sulfuric Acids / Q000494:pharmacology* / Q000633:toxicity; D014780:Viruses / Q000235:genetics
D000477:Alkylating Agents; D002273:Carcinogens; D009153:Mutagens; D013463:Sulfuric Acid Esters; D013464:Sulfuric Acids; D004247:DNA; C007482:dimethyl sulfate; C011612:diethyl sulfate