Transesterification of a series of 12 parabens by liver and small-intestinal microsomes of rats and humans |
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| Affiliation: | 1. Department of Medicine, University of Missouri, Columbia, MO 65212, United States;2. Department of Molecular Microbiology & Immunology, University of Missouri, Columbia, MO 65212, United States;3. Department of Surgery, University of Missouri, Columbia, MO 65212, United States;4. Department of Microbiology, Immunology and Pathology, Des Moines University, Des Moines, IA 50312, United States;1. Department of Nutrition and Food Science, University of Granada, Cartuja Campus, 18071, Granada, Spain;2. GENYO, Centre for Genomics and Oncological Research: Pfizer, University of Granada, Andalusian Regional Government, PTS Granada, Granada, Spain;3. Instituto de Investigación Biosanitaria ibs.GRANADA, Granada, Spain;4. Department of Preventive Medicine and Public Health, University of Granada, Cartuja Campus, 18071, Granada, Spain;5. Consortium for Biomedical Research in Epidemiology & Public Health (CIBER en Epidemiología y Salud Pública—CIBERESP), Monforte de Lemos 5, 2809, Madrid, Spain;6. Department of Legal Medicine and Toxicology, University of Granada, 18071, Granada, Spain;7. Department of Biochemistry and Molecular Biology III, University of Granada, Faculty of Medicine, PTS, Granada, Spain |
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| Abstract: | Hydrolytic transformation of parabens (4-hydroxybenzoic acid esters; used as antibacterial agents) to 4-hydroxybenzoic acid and alcohols by tissue microsomes is well-known both in vitro and in vivo. Here, we investigated transesterification reactions of parabens catalyzed by rat and human microsomes, using a series of 12 parabens with C1–C12 alcohol side chains. Transesterification of parabens by rat liver and small-intestinal microsomes occurred in the presence of alcohols in the microsomal incubation mixture. Among the 12 parabens, propylparaben was most effectively transesterified by rat liver microsomes with methanol or ethanol, followed by butylparaben. Relatively low activity was observed with longer-side-chain parabens. In contrast, small-intestinal microsomes exhibited higher activity towards moderately long side-chain parabens, and showed the highest activity toward octylparaben. When parabens were incubated with liver or small-intestinal microsomes in the presence of C1–C12 alcohols, ethanol and decanol were most effectively transferred to parabens by rat liver microsomes and small-intestinal microsomes, respectively. Human liver and small-intestinal microsomes also exhibited significant transesterification activities with different substrate specificities, like rat microsomes. Carboxylesterase isoforms, CES1b and CES1c, and CES2, exhibited significant transesterification activity toward parabens, and showed similar substrate specificity to human liver and small-intestinal microsomes, respectively. |
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| Keywords: | Paraben Transesterification Carboxylesterase Rat and human liver microsomes Rat and human small-intestinal microsomes Substrate specificity |
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