title: Saturated and monofluoro analogs of the oriental fruit fly attractant methyl eugenol show reduced genotoxic activities in yeast.
abstract: Methyl eugenol, is a commercially used fruit fly attractant and a suspected carcinogen. Several phenylpropenes, including methyl eugenol and the known carcinogen safrole, score negative in the Salmonella assay but score positive in the yeast DEL assay that selects for intrachromosomal recombination events in the yeast Saccharomyces cerevisiae. In an attempt to dissociate the beneficial properties of methyl eugenol from its genotoxic properties, saturated or fluorinated analogs were evaluated for their ability to induce intrachromosomal (DEL) recombination in yeast. Field tests have previously shown that all of the analogs used have appreciable properties as fruit fly attractants. The analogs 1,2-dimethoxy-4-ethylbenzene, 1,2-dimethoxy-4-(2-fluoro-2-propenyl)benzene, 1,2-dimethoxy-4-(2-fluoroethyl)benzene and 1,2-dimethoxy-4-(3-fluoro-2-propenyl)benzene all showed reduced toxicity and reduced recombinagenicity in yeast compared to methyl eugenol. These results confirm the validity of fluorination and/or removal of the 2-propenyl moiety in reducing the toxicity and recombinagenicity of methyl eugenol derivatives.
authors.affiliation: Department of Molecular and Cellular Toxicology, Harvard School of Public Health, Boston, MA 02115, USA. brennan@mbcrr.harvard.edu
authors.forename: R J
authors.initials: RJ
authors.lastname: Brennan
authors.forename: S
authors.initials: S
authors.lastname: Kandikonda
authors.forename: A P
authors.initials: AP
authors.lastname: Khrimian
authors.forename: A B
authors.initials: AB
authors.lastname: DeMilo
authors.forename: N J
authors.initials: NJ
authors.lastname: Liquido
authors.forename: R H
authors.initials: RH
authors.lastname: Schiestl
mesh_terms: D000818:Animals; D002630:Chemotactic Factors / Q000737:chemistry / Q000633:toxicity*; D004175:Diptera / Q000187:drug effects; D005054:Eugenol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000633:toxicity; D017611:Fluorine Compounds / Q000737:chemistry / Q000633:toxicity*; D009152:Mutagenicity Tests; D009153:Mutagens / Q000737:chemistry / Q000633:toxicity*; D012441:Saccharomyces cerevisiae / Q000187:drug effects*
chemical_list: D002630:Chemotactic Factors; D017611:Fluorine Compounds; D009153:Mutagens; C005223:methyleugenol; D005054:Eugenol