Cytosolic Acetyl Transfer and N-Deacetylation Associated with the Metabolism of Carcinogenic 2,4-Diaminotoluene in Rat Liver

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概要

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• Acetyl transfer and N-deacetylation associated with the metabolism of carcinogenic 2,4-diaminotoluene (2,4-DAT) were examined by detecting the products formed during the incubation of 2,4-DAT and its known urinary metabolites with the liver cytosol fraction from male Wistar rats. Data obtained from the incubation of 4-acetylamino-2-aminotoluene (4AA2AT) with the liver cytosol in the presence of 2,4-diaminobenzoic acid (2,4-DABA) indicated that the cytosol catalyzes the acetyl transfer between 4AA2AT and 2,4-DABA to produce 2,4-DAT and 2-acetylamino-4-aminobenzoic acid (2AA4ABA). The cytosol also catalyzed the acetyl transfer between 2,4-diacetylaminotoluene (2,4-DAAT) and 2,4-DABA to produce 2-acetylamino4-aminotoluene (2AA4AT) and 2AA4ABA. Without 2,4-DABA, the cytosol catalyzed the N-deacetylations of 4AA2AT and 2,4-DAAT to produce 2,4-DAT and 2AA4AT. 2AA4AT was inactive for both the N-deacetylation and the acetyl transfer. 2,4-DAT itself was N-acetylated to 4AA2AT by incubation with acetyl-CoA, but 2AA4AT and 2,4-DAAT were not detectable in the incubation product. However, both 2AA4AT and 4AA2AT were N-acetylated to 2,4-DAAT by incubation with acetyl-CoA. These findings suggest that 2,4-DAT is reproduced either by the N-deacetylation of 4AA2AT or by the acetyl transfer between 4AA2AT and 2,4-DABA in the metabolism of 2,4-DAT and further suggest that 2,4-DAAT is produced by the acetyl-CoA-dependent N-acetylation of 4AA2AT; 2AA4AT is produced either by the N-deacetylation of 2,4-DAAT or by the acetyl transfer between 2,4-DAAT and 2,4DABA. Based on these results, the metabolic pathway of 2,4-DAT in the rat is proposed.

• 公益社団法人日本薬学会の論文
• 2002-12-01

著者

• MORI Masa-aki

  Department of Health Sciences, School of Medicine, Kyushu University

• Mori Masa-aki

  Department Of Health Sciences School Of Medicine Kyushu University

• Sayama M

  Department Of Material Systems Engineering And Life Science Faculty Of Engineering Toyama University

• Mori Masa-aki

  School of Health Sciences, Kyushu University

• Kondo Takashi

  Faculty of Medicine, Toyama Medical and Pharmaceutical University

• Sayama Michio

  Department of Material Systems Engineering and Life Science, Faculty of Engineering, Toyama Universi

• Kondo Takashi

  Faculty Of Medicine Toyama Medical And Pharmaceutical University

• Kondo Takashi

  Faculty Of Agriculture Mie University

• SAYAMA Michio

  Department of Life Sciences and Bioengineering, Faculty of Engineering, University of Toyama

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