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pH对致癌物N-乙酰氧基-2-乙酰氨基芴与DNA反应后取代产物比例的影响。

Effect of pH on the ratio of substitution products in DNA after reaction with the carcinogen N-acetoxy-2-acetylaminofluorene.

作者信息

Kriek E

出版信息

Cancer Lett. 1979 Jul;7(2-3):141-6. doi: 10.1016/s0304-3835(79)80109-3.

DOI:10.1016/s0304-3835(79)80109-3
PMID:38901
Abstract

The substitution reaction products of N-acetoxy-2-acetylaminofluorene (N-AcO-AAF) and the N-sulfate (potassium salt) of N-hydroxy-4-acetyl-aminobiphenyl (N-OSO3K-AABP) with DNA from calf thymus were determined after reaction in buffered solutions of 0.10 M NaCl at pH values from 4--9. In the case of N-AcO-AAF, the ratio of N-(guanin-8-yl)-2-acetylaminofluorene (N-(guanine-8-yl)-AAF) to 3-(guanin-N2-yl)-2-acetylaminofluorene (3-(guanin-N2-yl)-AAF) increased 2.2 times over the entire pH range studied, starting at pH 9. With the N-OSO3K-AABP, the total substitution of guanine was much lower (22--34 times) as compared with N-AcO-AAF, and the ratio of N-(guanin-8-yl)-4-acetylaminobiphenyl to 3-(guanin-N2-yl)-4-acetylaminobiphenyl was not affected by a change in pH of the reaction medium. As expected, heat-denatured DNA reacted more extensively with both esters, but an increase in substitution was much more pronounced for the biphenyl derivative (9 times) than for the fluorene compound (2.8 times). Degradation, denaturation or interstrand cross-linking of DNA were not observed under the reaction conditions employed.

摘要

在pH值为4 - 9的0.10 M NaCl缓冲溶液中反应后,测定了N - 乙酰氧基 - 2 - 乙酰氨基芴(N - AcO - AAF)和N - 羟基 - 4 - 乙酰氨基联苯的N - 硫酸盐(钾盐)(N - OSO₃K - AABP)与小牛胸腺DNA的取代反应产物。对于N - AcO - AAF,从pH 9开始,在所研究的整个pH范围内,N - (鸟嘌呤 - 8 - 基) - 2 - 乙酰氨基芴(N - (鸟嘌呤 - 8 - 基) - AAF)与3 - (鸟嘌呤 - N₂ - 基) - 2 - 乙酰氨基芴(3 - (鸟嘌呤 - N₂ - 基) - AAF)的比例增加了2.2倍。对于N - OSO₃K - AABP,与N - AcO - AAF相比,鸟嘌呤的总取代量要低得多(22 - 34倍),并且反应介质pH的变化不影响N - (鸟嘌呤 - 8 - 基) - 4 - 乙酰氨基联苯与3 - (鸟嘌呤 - N₂ - 基) - 4 - 乙酰氨基联苯的比例。正如预期的那样,热变性DNA与两种酯的反应更广泛,但联苯衍生物的取代增加(9倍)比芴化合物(2.8倍)更明显。在所采用的反应条件下未观察到DNA的降解、变性或链间交联。

相似文献

1
Effect of pH on the ratio of substitution products in DNA after reaction with the carcinogen N-acetoxy-2-acetylaminofluorene.pH对致癌物N-乙酰氧基-2-乙酰氨基芴与DNA反应后取代产物比例的影响。
Cancer Lett. 1979 Jul;7(2-3):141-6. doi: 10.1016/s0304-3835(79)80109-3.
2
Quantification of adducts formed in DNA treated with N-acetoxy-2-acetylaminofluorene or N-hydroxy-2-aminofluorene: comparison of trifluoroacetic acid and enzymatic degradation.用N-乙酰氧基-2-乙酰氨基芴或N-羟基-2-氨基芴处理的DNA中形成的加合物的定量:三氟乙酸和酶促降解的比较。
Carcinogenesis. 1983 Aug;4(8):1001-6. doi: 10.1093/carcin/4.8.1001.
3
Association between DNA strand breaks and specific DNA adducts in murine hepatocytes following in vivo and in vitro exposure to N-hydroxy-2-acetylaminofluorene and N-acetoxy-2-acetylaminofluorene.在体内和体外暴露于N-羟基-2-乙酰氨基芴和N-乙酰氧基-2-乙酰氨基芴后,小鼠肝细胞中DNA链断裂与特定DNA加合物之间的关联。
Carcinogenesis. 1985 Jan;6(1):45-52. doi: 10.1093/carcin/6.1.45.
4
Rapid release of carcinogen-guanine adducts from DNA after reaction with N-acetoxy-2-acetylaminofluorene or N-benzoyloxy-N-methyl-4-aminoazobenzene.与 N-乙酰氧基-2-乙酰氨基芴或 N-苯甲酰氧基-N-甲基-4-氨基偶氮苯反应后,致癌物-鸟嘌呤加合物从 DNA 中快速释放。
Carcinogenesis. 1982;3(1):81-8. doi: 10.1093/carcin/3.1.81.
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C-alkylation of N-acetoxy-N-2-acetylaminofluorene: effects on its reaction with DNA in vitro.N-乙酰氧基-N-2-乙酰氨基芴的C-烷基化:对其体外与DNA反应的影响
Cancer Biochem Biophys. 1984 Jun;7(2):89-99.
6
Spectroscopic study of the effects of C-alkylation of N-acetoxy-N-acetyl-2-aminofluorene on some properties of the carcinogen-modified DNA.N-乙酰氧基-N-乙酰基-2-氨基芴的C-烷基化对致癌物修饰DNA某些性质影响的光谱研究
Cancer Biochem Biophys. 1983;6(4):261-7.
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Solvolysis and metabolic degradation, by rat liver, of the ultimate carcinogen, N-sulfonoxy-2-acetylaminofluorene.终极致癌物N-磺酰氧基-2-乙酰氨基芴在大鼠肝脏中的溶剂解和代谢降解。
Mol Pharmacol. 1987 Apr;31(4):438-45.
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Formation of DNA adducts from N-acetoxy-2-acetylaminofluorene and N-hydroxy-2-acetylaminofluorene in rat hemopoietic tissues in vivo.体内大鼠造血组织中由N-乙酰氧基-2-乙酰氨基芴和N-羟基-2-乙酰氨基芴形成DNA加合物的过程。
Cancer Res. 1986 Jan;46(1):233-8.
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An ELISA for detection of DNA-bound carcinogen using a monoclonal antibody to N-acetoxy-2-acetylaminofluorene-modified DNA.
J Immunol Methods. 1987 Apr 16;98(2):195-200. doi: 10.1016/0022-1759(87)90005-6.
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Interaction of the synthetic ultimate carcinogens, N-sulfonoxy- and N-acetoxy-2-acetylaminofluorene, and of enzymatically activated N-hydroxy-2-acetylaminofluorene with nucleophiles.合成终极致癌物N-磺酰氧基-和N-乙酰氧基-2-乙酰氨基芴,以及酶促活化的N-羟基-2-乙酰氨基芴与亲核试剂的相互作用。
Carcinogenesis. 1986 Mar;7(3):405-11. doi: 10.1093/carcin/7.3.405.

引用本文的文献

1
Reactivity of B and Z-DNA towards N-acetoxy-2-acetylaminofluorene.B型和Z型DNA对N-乙酰氧基-2-乙酰氨基芴的反应活性。
Nucleic Acids Res. 1982 Jul 24;10(14):4423-30. doi: 10.1093/nar/10.14.4423.