Journal Article

Correlation between DNA or protein adducts and benzo[<i>a</i>]pyrene diol epoxide I–triglyceride adduct detected <i>in vitro</i> and <i>in vivo</i>

Seung Jun Kwack and Byung Mu Lee

in Carcinogenesis

Volume 21, issue 4, pages 629-632
Published in print April 2000 | ISSN: 0143-3334
Published online April 2000 | e-ISSN: 1460-2180 | DOI:
Correlation between DNA or protein adducts and benzo[a]pyrene diol epoxide I–triglyceride adduct detected in vitro and in vivo

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In this study, we demonstrated the in vitro and in vivo formation of carcinogen–lipid adduct and its correlation with DNA or protein adducts. The lipids from serum or hepatocyte membranes of Sprague–Dawley rats, human serum and standard major lipids were in vitro reacted with benzo[a]pyrene (B[a]P) and B[a]P metabolites. 7,8-Dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene(BPDE-I), an ultimate carcinogenic form of B[a]P, was covalently bound to triglyceride (TG). BPDE-I–TG adducts isolated by thin-layer chromatography (TLC) were further detected by high-performance liquid chromatography. TGs, including triolein, tripalmitin and tristearin, showed positive reactions with BPDE-I. However, cholesterol, phospholipids (phosphatidylcholine, phosphatidyl-ethanolamine, phosphatidyl-inositol and sphingomyelin) and non-esterified fatty acids (palmitic acid, oleic acid, linoleic acid and stearic acid) did not react with BPDE-I. In addition, other B[a]P metabolites (B[a]P-phenols and -diols) did not react with TG. TG appeared to be the most reactive lipid yet studied with respect to its ability to form an adduct with BPDE-I. There was a clear-cut dose-related formation of [1,3-3H]BPDE-I–lipid adducts in vitro between TG and [1,3-3H]BPDE-I. In an animal study, BPDE-I–TG was also formed in the serum of rats orally treated with B[a]P (25 mg/rat). Also, obvious correlations between [3H]B[a]P related-biomolecule adducts (DNA or protein) or lipid damage and the BPDE-I–TG adducts were obtained in various tissues of mice i.p. treated with [3H]B[a]P. These data suggest that TG can form an adduct with BPDE-I, as do other macromolecules (DNA, RNA and protein). Therefore, a carcinogen–lipid adduct would be a useful biomarker for chemical carcinogenesis research and cancer risk assessment.

Keywords: B[a]P, benzo[a]pyrene; BPDE-I, 7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydro-benzo[a]pyrene (benzo[a]pyrene diol epoxide-I); HPLC, high-performance liquid chromatography; TG, triglyceride; THF, tetrahydrofuran; TLC, thin-layer chromatography.

Journal Article.  3415 words.  Illustrated.

Subjects: Clinical Cytogenetics and Molecular Genetics

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