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Research ArticleArticle

Intestinal Bioavailability and Biotransformation of 3-Hydroxybenzo(a)pyrene in an Isolated Perfused Preparation from Channel Catfish, Ictalurus punctatus

Margaret O. James, Zeen Tong, Laura Rowland-Faux, Changaram S. Venugopal and Kevin M. Kleinow
Drug Metabolism and Disposition May 2001, 29 (5) 721-728;
Margaret O. James
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Zeen Tong
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Laura Rowland-Faux
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Changaram S. Venugopal
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Kevin M. Kleinow
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Abstract

The intestinal bioavailability and biotransformation of 3-hydroxybenzo(a)pyrene, a major metabolite of benzo(a)pyrene in many animal species, was investigated in an in situ isolated intestinal preparation from the channel catfish, and in vitro with preparations of catfish intestine and blood. 3-Hydroxybenzo(a)pyrene was a good substrate for adenosine 3′-phosphate 5′-phosphosulfate (PAPS)-sulfotransferase and UDP-glucuronosyltransferase in cytosol or microsomes prepared from intestinal mucosa. The benzo(a)pyrene-3-glucuronide and 3-sulfate conjugates were only very slowly hydrolyzed by intestinal β-glucuronidase and sulfatase. The Kmvalues for PAPS-sulfotransferase and UDP-glucuronosyltransferase were 0.4 and 1 μM, respectively, and Vmax were 1.61 ± 1.08 nmol benzo(a)pyrene-3-sulfate/min/mg of cytosolic protein and 1.08 ± 0.54 nmol benzo(a)pyrene-3-glucuronide/min/mg of microsomal protein. Hydrolytic enzyme activities were three orders of magnitude slower. In the in situ intestinal preparation, [3H]3-hydroxybenzo(a)pyrene was readily metabolized to the glucuronide and sulfate conjugates. After 1 h of incubation of 2 or 20 μM [3H]3-hydroxybenzo(a)pyrene in the in situ preparation, the luminal contents contained 3-hydroxybenzo(a)pyrene, benzo(a)pyrene-3,6-dione, benzo(a)pyrene-3-sulfate, and benzo(a)pyrene-3-glucuronide. Mucosal samples contained these components, as well as some unextractable material. The blood contained mainly benzo(a)pyrene-3-sulfate and an as yet unidentified metabolite of 3-hydroxybenzo(a)pyrene bound to hemoglobin. Some, but not all, blood samples contained small amounts of 3-hydroxybenzo(a)pyrene, benzo(a)pyrene-3-glucuronide, and benzo(a)pyrene-3,6-dione. These studies demonstrate the rapid phase 2 conjugation of a phenolic benzo(a)pyrene metabolite in intestinal mucosa, and the transfer of the phase 2 sulfate and glucuronide conjugates to blood.

Footnotes

  • Send reprint requests to: Dr. Margaret O. James, Department of Medicinal Chemistry, P.O. Box 100485, College of Pharmacy, University of Florida, Gainesville, FL 32610-0485. E-mail:mojames{at}ufl.edu

  • ↵1 Present address: Wyeth-Ayerst Research, Department of Biotransformation, CN 8000, Princeton, NJ 08543-8000.

  • This work was supported by Grant ES 05781 from the U.S. Public Health Service. A preliminary report was presented at the Society of Toxicology annual meeting, Baltimore, MD, 1995.

  • Abbreviations used are::
    PAH
    polycyclic aromatic hydrocarbons
    BaP
    benzo(a)pyrene
    3-OH-BaP
    3-hydroxybenzo(a)pyrene
    BaP-3-glucuronide
    benzo(a)pyrene-3-β-d-glucopyranosiduronic acid
    BaP-3-sulfate
    benzo(a)pyrene-3-sulfate
    BaP-3,6-dione
    benzo(a)pyrene-3,6-dione
    PAPS
    adenosine 3′-phosphate 5′-phosphosulfate
    SULT
    PAPS-sulfotransferase
    UGT
    UDP-glucuronosyltransferase
    BNF
    β-naphthoflavone
    HPLC
    high-performance liquid chromatography
    NCI
    National Cancer Institute
    • Received November 7, 2000.
    • Accepted February 1, 2001.
  • The American Society for Pharmacology and Experimental Therapeutics
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Drug Metabolism and Disposition: 29 (5)
Drug Metabolism and Disposition
Vol. 29, Issue 5
1 May 2001
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Research ArticleArticle

Intestinal Bioavailability and Biotransformation of 3-Hydroxybenzo(a)pyrene in an Isolated Perfused Preparation from Channel Catfish, Ictalurus punctatus

Margaret O. James, Zeen Tong, Laura Rowland-Faux, Changaram S. Venugopal and Kevin M. Kleinow
Drug Metabolism and Disposition May 1, 2001, 29 (5) 721-728;

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Research ArticleArticle

Intestinal Bioavailability and Biotransformation of 3-Hydroxybenzo(a)pyrene in an Isolated Perfused Preparation from Channel Catfish, Ictalurus punctatus

Margaret O. James, Zeen Tong, Laura Rowland-Faux, Changaram S. Venugopal and Kevin M. Kleinow
Drug Metabolism and Disposition May 1, 2001, 29 (5) 721-728;
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