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4-氨基偶氮苯、N-羟基-4-氨基偶氮苯及其衍生物在大鼠和小鼠原代肝细胞培养物中诱导的非程序性DNA合成。

Unscheduled DNA synthesis induced by 4-aminoazobenzene, N-hydroxy-4-aminoazobenzene, and their derivatives in primary cultures of rat and mouse hepatocytes.

作者信息

Watanabe H K, Hashimoto Y

出版信息

Gan. 1981 Dec;72(6):930-6.

PMID:7341341
Abstract

The ability of carcinogenic and non-carcinogenic aminoazo dyes to induce unscheduled DNA synthesis (UDS) in primary cultures of hepatocytes of 3 strains of rats and 2 strains of mice was examined by means of microautoradiography. Azo dyes tested were 4-aminoazobenzene (AAB) and 4 of its ring methoxyl (MeO) derivatives, their N-hydroxy (N-OH) derivatives, N-methyl-4-aminoazobenzene (MAB) and its N-bezoyloxy derivative, and N,N-dimethyl-4-aminoazobenzene (DAB). All carcinogenic aminoazo dyes (AAB, 3-MeO-AAB, 4'-MeO-AAB, MAB and DAB), but not the non-carcinogenic dyes (2-MeO-AAB and 2,5-diMeO-AAB), induced UDS in rat hepatocytes as well as mouse hepatocytes. N-Hydroxy derivatives of AAB and its 3- and 4'-MeO derivatives elicited higher levels of UDS than did the corresponding mother aminoazo dyes. N-OH-2-MeO-AAB was as inactive with rat hepatocytes as the mother dye. N-OH-2,5-diMeO-AAB, however, elicited a definite level of UDS, in contrast to the mother 2,5-diMeO-AAB. N-Benzoyloxy-MAB, a prototype compound of the ultimate carcinogenic metabolite of MAB, was as active as the mother MAB. N,-OH-3-MeO-AAB induced UDS more rapidly than did 3-MeO-AAB. The UDS elicited by 3-MeO-AAB was found to end within a few hours after releasing the hepatocytes from the azo dye.

摘要

通过微放射自显影法检测了致癌和非致癌氨基偶氮染料在3个大鼠品系和2个小鼠品系的原代肝细胞培养物中诱导非预定DNA合成(UDS)的能力。所检测的偶氮染料有4-氨基偶氮苯(AAB)及其4种环甲氧基(MeO)衍生物、它们的N-羟基(N-OH)衍生物、N-甲基-4-氨基偶氮苯(MAB)及其N-苯甲酰氧基衍生物,以及N,N-二甲基-4-氨基偶氮苯(DAB)。所有致癌性氨基偶氮染料(AAB、3-MeO-AAB、4'-MeO-AAB、MAB和DAB),而非致癌染料(2-MeO-AAB和2,5-二MeO-AAB),均可在大鼠肝细胞和小鼠肝细胞中诱导UDS。AAB及其3-和4'-MeO衍生物的N-羟基衍生物诱导的UDS水平高于相应的母体氨基偶氮染料。N-OH-2-MeO-AAB对大鼠肝细胞的活性与母体染料相同。然而,与母体2,5-二MeO-AAB相比,N-OH-2,5-二MeO-AAB可诱导一定水平的UDS。MAB最终致癌代谢产物的原型化合物N-苯甲酰氧基-MAB与母体MAB活性相同。N,-OH-3-MeO-AAB诱导UDS的速度比3-MeO-AAB更快。发现3-MeO-AAB诱导的UDS在将肝细胞从偶氮染料中释放后数小时内结束。

相似文献

1
Unscheduled DNA synthesis induced by 4-aminoazobenzene, N-hydroxy-4-aminoazobenzene, and their derivatives in primary cultures of rat and mouse hepatocytes.4-氨基偶氮苯、N-羟基-4-氨基偶氮苯及其衍生物在大鼠和小鼠原代肝细胞培养物中诱导的非程序性DNA合成。
Gan. 1981 Dec;72(6):930-6.
2
Amino acid conjugation of N-hydroxy-4-aminoazobenzene dyes: a possible activation process of carcinogenic 4-aminoazobenzene dyes to the ultimate mutagenic or carcinogenic metabolites.N-羟基-4-氨基偶氮苯染料的氨基酸结合:致癌性4-氨基偶氮苯染料向最终诱变或致癌代谢物的一种可能激活过程。
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Carcinogenicities of 3-methoxy-4-aminoazobenzene, N-hydroxy-3-methoxy-4-aminoazobenzene and related azo dyes in the mouse.3-甲氧基-4-氨基偶氮苯、N-羟基-3-甲氧基-4-氨基偶氮苯及相关偶氮染料对小鼠的致癌性
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Gan. 1981 Dec;72(6):921-9.
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The N-hydroxy metabolites of N-methyl-4-aminoazobenzene and related dyes as proximate carcinogens in the rat and mouse.N-甲基-4-氨基偶氮苯及相关染料的N-羟基代谢产物作为大鼠和小鼠的直接致癌物
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The carcinogenicity of methoxyl derivatives of 4-aminoazobenzene: correlation between DNA adducts and genotoxicity.4-氨基偶氮苯甲氧基衍生物的致癌性:DNA加合物与遗传毒性之间的相关性。
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32P-postlabeling analysis of DNA adducts in rat livers after treatment with genotoxic and non-genotoxic 4-aminoazobenzene derivatives.用遗传毒性和非遗传毒性4-氨基偶氮苯衍生物处理大鼠肝脏后,对DNA加合物进行32P后标记分析。
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4-aminoazobenzene and N,N-dimethyl-4-aminoazobenzene as equipotent hepatic carcinogens in male C57BL/6 X C3H/He F1 mice and characterization of N-(Deoxyguanosin-8-yl)-4-aminoazobenzene as the major persistent hepatic DNA-bound dye in these mice.4-氨基偶氮苯和N,N-二甲基-4-氨基偶氮苯作为雄性C57BL/6×C3H/He F1小鼠中具有同等效力的肝致癌物以及N-(脱氧鸟苷-8-基)-4-氨基偶氮苯作为这些小鼠肝脏中主要持久性DNA结合染料的特性
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Mutat Res. 1985 Nov-Dec;152(2-3):125-9. doi: 10.1016/0027-5107(85)90054-5.

引用本文的文献

1
Oxidative DNA damage induced by an N-hydroxy metabolite of carcinogenic 4-dimethylaminoazobenzene.致癌性4-二甲基氨基偶氮苯的N-羟基代谢产物诱导的氧化性DNA损伤。
Jpn J Cancer Res. 2001 Jan;92(1):23-9. doi: 10.1111/j.1349-7006.2001.tb01043.x.