Stereospecific hydrolysis of a phosphoramidate used as an OPIDP model by human sera with PON1 192 alloforms

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• 作者：Antonio Monroy-Noyola ; Bertín Trujillo ; Petra Yescas…
• 关键词：Organophosphorus ; Human serum ; Chiral ; Hydrolysis ; Paraoxonase ; 1 ; Stereospecificity
• 刊名：Archives of Toxicology
• 出版年：2015
• 出版时间：October 2015
• 年：2015
• 卷：89
• 期：10
• 页码：1801-1809
• 全文大小：502 KB
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• 作者单位：Antonio Monroy-Noyola (1)
  Bertín Trujillo (1)
  Petra Yescas (2)
  Fernanda Martínez-Salazar (1)
  Sara García-Jiménez (1)
  Camilo Ríos (3)
  Eugenio Vilanova (4)
  
  1. Laboratorio de Neuroprotección, Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001 Col. Chamilpa, 62209, Cuernavaca, Morelos, Mexico
  2. Departamento de Neurogenética, Instituto Nacional de Neurología y Neurocirugía, M.V.S., Mexico, DF, Mexico
  3. Departamento de Neuroquímica, Instituto Nacional de Neurología y Neurocirugía, M.V.S., Mexico, DF, Mexico
  4. Unidad de Toxicología y Seguridad Química, Instituto de Bioingeniería, Universidad Miguel Hernández, Elche, Alicante, Spain
  
• 刊物主题：Pharmacology/Toxicology; Occupational Medicine/Industrial Medicine; Environmental Health; Biomedicine general;
• 出版者：Springer Berlin Heidelberg
• ISSN：1432-0738

文摘

O-hexyl 2,5-dichlorophenyl phosphoramidate (HDCP) is a racemic organophosphate compound (OP) that induces delayed neuropathy in vivo. The O-hexyl 2,5-dichlorophenyl phosphoramidate R (R-HDCP) isomer inhibits and ages neuropathic target esterase (NTE) in hen brain. Moreover, human serum paraoxonase-1 (PON1) is a Ca2+-dependent enzyme capable of hydrolyzing OPs. The enzymatic activity of PON1 against OPs depends on the genetic polymorphisms present at position 192 (glutamine or arginine). The catalytic efficiency of PON1 is an important factor that determines neurotoxic susceptibility to some OPs. In the present study, we characterized the stereospecific hydrolysis of HDCP by alloforms PON1 Q192R human serum by chiral chromatography. Forty-seven human samples were characterized for the PON1 192 polymorphism. The hydrolysis data demonstrate that the three alloforms of PON1 show an exclusive and significant stereospecific Ca2+-dependent hydrolysis of O-hexyl 2,5-dichlorophenyl phosphoramidate S isomer (S-HDCP) at 19-27 μM at the concentrations that remain in all the samples. This stereoselective Ca2+-dependent hydrolysis of S-HDCP is inhibited by EDTA and is independent of the PON1 Q192R alloform. The present research reinforces the hypothesis that R-HDCP (an isomer that inhibits and causes NTE aging) is the enantiomer that induces delayed neuropathy by this chiral phosphoramidate due to the low hydrolysis level of the R-HDCP observed in this study. Keywords Organophosphorus Human serum Chiral Hydrolysis Paraoxonase-1 Stereospecificity