Brennan R J, Kandikonda S, Khrimian A P, DeMilo A B, Liquido N J, Schiestl R H
Department of Molecular and Cellular Toxicology, Harvard School of Public Health, Boston, MA 02115, USA.
Mutat Res. 1996 Aug 12;369(3-4):175-81. doi: 10.1016/s0165-1218(96)90024-5.
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.
甲基丁香酚是一种商业上使用的果蝇引诱剂，也是一种疑似致癌物。几种苯丙烯，包括甲基丁香酚和已知的致癌物黄樟素，在沙门氏菌试验中呈阴性，但在酵母DEL试验中呈阳性，该试验用于筛选酿酒酵母中的染色体内重组事件。为了将甲基丁香酚的有益特性与其遗传毒性特性区分开来，对饱和或氟化类似物诱导酵母染色体内（DEL）重组的能力进行了评估。此前的田间试验表明，所有使用的类似物都具有作为果蝇引诱剂的显著特性。与甲基丁香酚相比，类似物1,2-二甲氧基-4-乙苯、1,2-二甲氧基-4-（2-氟-2-丙烯基）苯、1,2-二甲氧基-4-（2-氟乙基）苯和1,2-二甲氧基-4-（3-氟-2-丙烯基）苯在酵母中均表现出较低的毒性和较低的致突变性。这些结果证实了氟化和/或去除2-丙烯基部分在降低甲基丁香酚衍生物的毒性和致突变性方面的有效性。
