Reference

Induction of unscheduled DNA synthesis in HeLa cells by allylic compounds

Induction of unscheduled DNA synthesis in HeLa cells by allylic compounds. Schiffmann, Dietmar; Eder, Erwin; Neudecker, Tilman; Henschler, Dietrich (Inst. Toxicol.In this study， 115-07-1 and 10061-02-6 are also used., Univ. Wuerzburg, Wuerzburg D-8700, Fed. Rep. Ger.). Cancer Lett. (Shannon, Irel.), 20(3), 263-9 (English) 1983. CODEN: CALEDQ. ISSN: 0304-3835. DOCUMENT TYPE: Journal CA Section: 4 (Toxicology) Thirteen allylic compds., mostly with close structural relation, were tested for their ability to induce unscheduled DNA synthesis (UDS) in HeLa cells and mutations in the Ames test; 11 induced UDS dose dependently. Allyl isothiocyanate [57-06-7] was neg. in UDS (borderline in the Ames test) and acrolein [107-02-8] (pos. in the Ames test) proved toxic to HeLa cells; thus, UDS measurement was excluded. In general, pos. qual. and quant. correlation between UDS, Ames test, and alkylating properties (as measured in the 4-nitrobenzylpyridine test) were found. Among structural analogs and typical allylic compds. with various leaving groups, the amt. of induced DNA repair at equimolar concns. decreased in the same order as the mutagenic and alkylating activities in the other 2 test systems: cis-1,3-dichloropropene [10061-01-5] > trans-1,3-dichloropropene [10061-02-6] > 2,3,-dichloro-1-propene [78-88-6]; 1-chloro-2-butene [591-97-9] > 3-chloro-1-butene [563-52-0] > 3-chloro-2-methyl-1-propene [563-47-3] > allyl chloride [107-05-1]; allyl methanesulfonate [6728-21-8] > allyl iodide [556-56-9] > allyl bromide [106-95-6] > allyl chloride. .

Genotoxicity of allyl compounds - a quick screening strategy based on structure-activity relationships and a battery of prescreening tests

Genotoxicity of allyl compounds - a quick screening strategy based on structure-activity relationships and a battery of prescreening tests. Eder, E.; Schiffmann, D.; Dornbusch, K.; Kuett, W.; Hoffman, C. (Inst. Toxicol., Wuerzburg 8700, Fed. Rep. Ger.). Food Chem. Toxicol., 24(6-7), 667-73 (English) 1986. CODEN: FCTOD7. ISSN: 0278-6915. DOCUMENT TYPE: Journal CA Section: 4 (Toxicology) A proposed strategy for the rapid screening of the genotoxic activities of allylic compds. is based on structure-activity relationships elaborated by a battery of quick screening tests. The procedure facilitates the selection of appropriate representatives of this class of compd. for subsequent testing, so that both expensive and time-consuming assays and the use of animals can be drastically reduced. Allylic compds. with suitable leaving groups exerted direct genotoxic activity. In the metabolic activation of these compds. the formation of epoxides is clearly of minor importance, playing a role only in the case of 2,3-dichloro-1-propene [78-88-6] and some of its homologs, whereas all reactive allylic compds. can be activated to genotoxic a,b-unsatd. carbonyl compds. (acrolein). The most significant factors for genotoxicity are the leaving groups and halogen substituents. Alkyl substituents increase the direct genotoxicity while decreasing the indirect activity (via acroleins).