Turchi G, Bonatti S, Citti L, Gervasi P G, Abbondandolo A
Mutat Res. 1981 Oct;83(3):419-30. doi: 10.1016/0027-5107(81)90023-3.
The mutagenicity of the epoxides 4-vinyl-1,2-epoxycyclohexane, 4-epoxyethyl-1,2-epoxycyclohexane, 4-epoxyethyl-1,2-dihydroxycyclohexane, 1,2-epoxycyclohexane and styrene oxide was assayed on the TA100 strain of S. typhimurium and V79 Chinese hamster cells. In the latter cell system, both point mutation (6-thioguanine resistance) and chromosomal damage (anaphase bridges and micronuclei) were scored. Genetic effects were related to the alkylating properties of the epoxides. For this purpose, alkylation of 4-(p-nitrobenzyl)pyridine (NBP) and sodium-p-nitrothiophenolate (NTP) was measured and values for the substrate constant (s) were calculated. 4-Epoxyethyl-1,2-epoxycyclohexane, 1,2-epoxycyclohexane and styrene oxide, characterized by the highest reactivity toward NBP and by an s value in the vicinity of 1, were mutagenic in all test systems. 4-Vinyl-1,2-epoxycyclohexane and 4-epoxyethyl-1,2-dihydroxycyclohexane, characterized by lower NBP reactivity and higher s value (1.30-1.38), did not induce reversion in S. typhimurium or 6-thioguanine-resistant mutants in V79 cells, but were as effective as the 3 other compounds in the induction of chromosomal damage.
在鼠伤寒沙门氏菌TA100菌株和V79中国仓鼠细胞上测定了4-乙烯基-1,2-环氧环己烷、4-环氧乙基-1,2-环氧环己烷、4-环氧乙基-1,2-二羟基环己烷、1,2-环氧环己烷和氧化苯乙烯的诱变性。在后者的细胞系统中，对点突变（6-硫鸟嘌呤抗性）和染色体损伤（后期桥和微核）都进行了评分。遗传效应与环氧化物的烷基化特性有关。为此，测定了4-(对硝基苄基)吡啶（NBP）和对硝基硫酚钠（NTP）的烷基化，并计算了底物常数（s）的值。4-环氧乙基-1,2-环氧环己烷、1,2-环氧环己烷和氧化苯乙烯对NBP具有最高的反应活性，且s值在1左右，在所有测试系统中都具有诱变性。4-乙烯基-1,2-环氧环己烷和4-环氧乙基-1,2-二羟基环己烷对NBP的反应活性较低，s值较高（1.30-1.38），在鼠伤寒沙门氏菌中不诱导回复突变，在V79细胞中也不诱导6-硫鸟嘌呤抗性突变体，但在诱导染色体损伤方面与其他3种化合物效果相同。
