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Structure-activity analysis of fluorinated 1-N-arylamino-1-arylmethanephosphonic acid esters as inhibitors of the NADH:ubiquinone oxidoreductase (complex I).

作者信息

Dronia H, Gruss U, Hägele G, Friedrich T, Weiss H

机构信息

Institut für Anorganische Chemie und Strukturchemia I, Heinrich-Heine-Universität Düsseldorf, Germany.

出版信息

J Comput Aided Mol Des. 1996 Apr;10(2):100-6. doi: 10.1007/BF00402818.

DOI:10.1007/BF00402818
PMID:8741014
Abstract

The structural and electronic properties of fluorinated 1-N-arylamino-1-arylmethanephosphonic acid esters were studied and related to the inhibitory effects on NADH:ubiquinone oxidoreductase (complex I). Electrostatic potential surfaces, dipole moments and molecular geometries were analysed. Based on the conformational analysis and the electronic parameters, a simple model for the active site of the fluorinated 1-N-arylamino-1-arylmethanephosphonic acid esters was developed, explaining the inhibitory power. The strongest inhibition effects were found for the 1-(N-4-trifluoromethoxyphenyl)-amino-1-phenylmethanephosphonic acid diethyl ester 1bab.

摘要

相似文献

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本文引用的文献

1
Two binding sites of inhibitors in NADH: ubiquinone oxidoreductase (complex I). Relationship of one site with the ubiquinone-binding site of bacterial glucose:ubiquinone oxidoreductase.抑制剂在NADH：泛醌氧化还原酶（复合体I）中的两个结合位点。其中一个位点与细菌葡萄糖：泛醌氧化还原酶的泛醌结合位点的关系。
Eur J Biochem. 1994 Jan 15;219(1-2):691-8. doi: 10.1111/j.1432-1033.1994.tb19985.x.
2
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The respiratory-chain NADH dehydrogenase (complex I) of mitochondria.
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Redox-linked proton translocation by NADH-ubiquinone reductase (complex I).由NADH-泛醌还原酶（复合体I）介导的氧化还原相关质子转运
J Bioenerg Biomembr. 1991 Oct;23(5):743-54. doi: 10.1007/BF00785999.
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The acridones, new inhibitors of mitochondrial NADH: ubiquinone oxidoreductase (complex I).
Biochim Biophys Acta. 1992 Mar 13;1099(3):262-6. doi: 10.1016/0005-2728(92)90036-2.
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Diseases of the mitochondrial DNA.
Annu Rev Biochem. 1992;61:1175-212. doi: 10.1146/annurev.bi.61.070192.005523.
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