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Bioorg Chem ; 75: 265-273, 2017 12.
Artigo em Inglês | MEDLINE | ID: mdl-29054071

RESUMO

In this paper, we report the inactivation of copper containing bovine plasma amine oxidase (BPAO) by a series of saturated alkylamines containing halogen atoms at γ-position, which are 1,1,1-trihalo-3-aminopropane, 1,1,1-trifluoro-2-hydroxy-3-aminopropane, 1,1,1-trichloro-2-hydroxy-3-aminopropane, and 1,1,1-trichloro-2-(2-phenethyloxy)-3-aminopropane. The trihalo-2-hydroxypropylamine analogs exhibited a time-dependent inactivation behavior of BPAO, with 1,1,1-trifluoro-2-hydroxy-3-aminopropane as the most efficient inactivator. The incorporation of a OH group at ß-position increased inactivation efficiency by 10-fold within the trifluoro analogs, and the incorporation of a phenethyloxy group at ß-position exhibited a higher efficiency by 3-fold within the trichloro analogs based on I75 values. All four compounds were found to be irreversible inactivators for BPAO.


Assuntos
Amina Oxidase (contendo Cobre)/antagonistas & inibidores , Inibidores Enzimáticos/química , Propano/química , Amina Oxidase (contendo Cobre)/metabolismo , Animais , Domínio Catalítico , Bovinos , Ensaios Enzimáticos , Inibidores Enzimáticos/síntese química , Inibidores Enzimáticos/metabolismo , Concentração Inibidora 50 , Cinética , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Propano/metabolismo
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