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Chemical structure and mutagenic activity of aminoimidazoquinolines and aminonaphthimidazoles related to 2-amino-3-methylimidazo[4,5-f]quinoline.

作者信息

Kaiser G, Harnasch D, King M T, Wild D

出版信息

Chem Biol Interact. 1986 Jan;57(1):97-106. doi: 10.1016/0009-2797(86)90052-9.

DOI:10.1016/0009-2797(86)90052-9
PMID:3512112
Abstract

We have synthesized 11 heterocyclic aromatic amines with chemical structures related to that of 2-amino-3-methylimidazo [4,5-f] quinoline (IQ), a potent mutagen occurring in broiled sardines, fried beef and beef extract. The mutagenic activity of these IQ analogs was studied and compared with that of IQ using the Ames test with strain TA98 of Salmonella typhimurium in presence of a metabolic activation system (S9 mix) derived from rat liver. The mutagenic activities of the IQ analogs vary over a million-fold; structure-activity comparisons indicate major contributions of the methyl substitution in the imidazole ring and of the quinoline-N, and significant contributions of methylation of the exocyclic amino group and of the geometry of the entire ring system.

摘要

相似文献

1
Chemical structure and mutagenic activity of aminoimidazoquinolines and aminonaphthimidazoles related to 2-amino-3-methylimidazo[4,5-f]quinoline.
Chem Biol Interact. 1986 Jan;57(1):97-106. doi: 10.1016/0009-2797(86)90052-9.
2
Effect of methyl substitution on mutagenicity of 2-amino-3-methylimidazo[4,5-f]quinoline, isolated from broiled sardine.甲基取代对从烤沙丁鱼中分离出的2-氨基-3-甲基咪唑并[4,5-f]喹啉致突变性的影响。
Carcinogenesis. 1981;2(11):1147-9. doi: 10.1093/carcin/2.11.1147.
3
Genotoxic activity of the N-acetylated metabolites of the food mutagens 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and 2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ).食品诱变剂2-氨基-3-甲基咪唑[4,5-f]喹啉（IQ）和2-氨基-3,4-二甲基咪唑[4,5-f]喹啉（MeIQ）的N-乙酰化代谢产物的遗传毒性活性。
Mutagenesis. 1988 Jul;3(4):303-9. doi: 10.1093/mutage/3.4.303.
4
Mutagenic activity of three synthetic isomers of the food carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) in the Ames test.
Mutat Res. 1993 Dec;319(4):273-8. doi: 10.1016/0165-1218(93)90015-6.
5
Prostaglandin-H synthase mediated metabolism and mutagenic activation of 2-amino-3-methylimidazo [4,5-f] quinoline (IQ).前列腺素-H合酶介导的2-氨基-3-甲基咪唑[4,5-f]喹啉（IQ）的代谢及诱变激活作用
Arch Toxicol. 1995;69(3):171-9. doi: 10.1007/s002040050154.
6
The synthesis and mutagenicity of the 3-ethyl analogues of the potent mutagens IQ, MeIQ, MeIQx and its 3,7-dimethyl isomer.强效诱变剂IQ、MeIQ、MeIQx及其3,7-二甲基异构体的3-乙基类似物的合成与致突变性。
Mutat Res. 1985 Nov;144(3):131-6. doi: 10.1016/0165-7992(85)90128-9.
7
Modulation of the mutagenic effects of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and 2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ) in bacteria with rat-liver 9000 x g supernatant or monolayers of rat hepatocytes as an activation system.以大鼠肝脏9000×g上清液或大鼠肝细胞单层作为激活系统，对细菌中2-氨基-3-甲基咪唑并[4,5-f]喹啉（IQ）和2-氨基-3,4-二甲基咪唑并[4,5-f]喹啉（MeIQ）的诱变作用进行调节。
Mutat Res. 1988 Jan;197(1):39-49. doi: 10.1016/0027-5107(88)90138-8.
8
Differential mutagenic activity of IQ (2-amino-3-methylimidazo[4,5-f]quinoline) in Salmonella typhimurium strains in vitro and in vivo, in Drosophila, and in mice.IQ（2-氨基-3-甲基咪唑[4,5-f]喹啉）在鼠伤寒沙门氏菌菌株中的体外和体内、果蝇及小鼠中的差异诱变活性。
Mutat Res. 1985 Apr-May;156(1-2):93-102. doi: 10.1016/0165-1218(85)90011-4.
9
The inhibition by flavonoids of 2-amino-3-methylimidazo[4,5-f]quinoline metabolic activation to a mutagen: a structure-activity relationship study.黄酮类化合物对2-氨基-3-甲基咪唑[4,5-f]喹啉代谢活化为诱变剂的抑制作用：构效关系研究
Mutat Res. 1997 Sep 5;379(1):21-32. doi: 10.1016/s0027-5107(97)00085-7.
10
Mutagenicity of some synthetic quinolines and quinoxalines related to IQ, MeIQ or MeIQx in Ames test.某些与IQ、MeIQ或MeIQx相关的合成喹啉和喹喔啉在艾姆斯试验中的致突变性。
Mutat Res. 1984 Jul;137(1):29-32. doi: 10.1016/0165-1218(84)90108-3.

引用本文的文献

1
The C8-2'-deoxyguanosine adduct of 2-amino-3-methylimidazo[1,2-d]naphthalene, a carbocyclic analogue of the potent mutagen 2-amino-3-methylimidazo[4,5-f]quinoline, is a block to replication in vitro.2-氨基-3-甲基咪唑[1,2-d]萘的 C8-2'-脱氧鸟苷加合物，是强诱变剂 2-氨基-3-甲基咪唑[4,5-f]喹啉的碳环类似物，是体外复制的阻断物。
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