Selective recognition of substituted chrysene-diol epoxide-2-DNA adducts by antiserum prepared against DNA adducts of benzo[c]-phenanthrene-diol epoxide-2

Heidi J. Einolf, Maritha A. Gross, Elizabeth R. Butch, Jyh ming Lin, Shantu Amin, Haruhiko Yagi, Donald M. Jerina, William M. Baird

Research output: Contribution to journalArticle

Abstract

Polyclonal antiserum prepared against DNA that was modified with racemic benzo[c]phenanthrene-3,4-diol-1,2-epoxide-2 (B[c]PhDE-2; benzylic hydroxyl and epoxide oxygen trans) was characterized for specificity of antigen recognition. Previous studies have demonstrated that the antisera stereoselectively recognized B[c]PhDE-2-DNA and failed to recognize DNA modified with racemic benzo[c]phenanthrene-3,4-diol-1,2-epoxide-1 (B[c]PhDE-1-DNA, benzylic hydroxyl and epoxide oxygen cis), benzo[a]pyrene-7,8-diol-9, 10-epoxide-2-DNA (B[a]PDE-2-DNA) and 7,12-dimethylbenz-[a]anthracene-3,4-diol-1,2-epoxide-1-DNA (DMBADE-1-DNA). DNA samples modified by diol-epoxide-2 diastereomers of several hydrocarbons were tested in competitive ELISA assays utilizing B[c]PhDE-2-DNA (270 fmol adducts per well). DNA modified with racemic diol-epoxide-2 of various substituted chrysenes (including chrysene, benzo[g]chrysene (B[g]C), 6-methylchrysene (6-MeC), and 5-methychrysene (5-MeC), gave 50% inhibition of antisera binding at significantly higher concentrations (5 to 7-fold) than the parent B[c]PhDE-2-DNA or 5,6-diMeCDE-DNA. DNA modified with 5,7-dimethylchryseneDE-2 (5,7-diMeCDE-2) and dibenzo[a,l]pyreneDE-2 (DB[a,l) PDE-2) required 20 and > 100-fold greater levels of adducts to give 50% inhibition. Results with B[c]Ph, 5,6-diMeC, chrysene, 6-MeC and 5-MeC diol epoxide-2-DNA indicate that substitution of a methyl group in the vicinity of the bay-region of the PAH-molecule had limited effects on antigen recognition by this antiserum. However, the addition of a ring or methyl group remote from the diol epoxide moiety, as in DB[a,l] PDE-2-DNA or 5,7-diMeCDE-2-DNA greatly decreased antigen recognition. The ability of this antiserum to recognize DNA adducts of a particular class of polycyclic aromatic hydrocarbons will be useful for studies of their contribution to the DNA-binding that results from exposure to complex environmental mixtures.

Original languageEnglish (US)
Pages (from-to)125-138
Number of pages14
JournalPolycyclic Aromatic Compounds
Volume12
Issue number2
DOIs
StatePublished - Jan 1 1997

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DNA Adducts
Epoxy Compounds
Immune Sera
DNA
Antigens
benzo(c)phenanthrene
chrysene
Polycyclic aromatic hydrocarbons
Chrysenes
Hydroxyl Radical
7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide
Oxygen
Anthracene
Polycyclic Aromatic Hydrocarbons
Pyrene
Hydrocarbons

All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

Cite this

Einolf, Heidi J. ; Gross, Maritha A. ; Butch, Elizabeth R. ; Lin, Jyh ming ; Amin, Shantu ; Yagi, Haruhiko ; Jerina, Donald M. ; Baird, William M. / Selective recognition of substituted chrysene-diol epoxide-2-DNA adducts by antiserum prepared against DNA adducts of benzo[c]-phenanthrene-diol epoxide-2. In: Polycyclic Aromatic Compounds. 1997 ; Vol. 12, No. 2. pp. 125-138.
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title = "Selective recognition of substituted chrysene-diol epoxide-2-DNA adducts by antiserum prepared against DNA adducts of benzo[c]-phenanthrene-diol epoxide-2",
abstract = "Polyclonal antiserum prepared against DNA that was modified with racemic benzo[c]phenanthrene-3,4-diol-1,2-epoxide-2 (B[c]PhDE-2; benzylic hydroxyl and epoxide oxygen trans) was characterized for specificity of antigen recognition. Previous studies have demonstrated that the antisera stereoselectively recognized B[c]PhDE-2-DNA and failed to recognize DNA modified with racemic benzo[c]phenanthrene-3,4-diol-1,2-epoxide-1 (B[c]PhDE-1-DNA, benzylic hydroxyl and epoxide oxygen cis), benzo[a]pyrene-7,8-diol-9, 10-epoxide-2-DNA (B[a]PDE-2-DNA) and 7,12-dimethylbenz-[a]anthracene-3,4-diol-1,2-epoxide-1-DNA (DMBADE-1-DNA). DNA samples modified by diol-epoxide-2 diastereomers of several hydrocarbons were tested in competitive ELISA assays utilizing B[c]PhDE-2-DNA (270 fmol adducts per well). DNA modified with racemic diol-epoxide-2 of various substituted chrysenes (including chrysene, benzo[g]chrysene (B[g]C), 6-methylchrysene (6-MeC), and 5-methychrysene (5-MeC), gave 50{\%} inhibition of antisera binding at significantly higher concentrations (5 to 7-fold) than the parent B[c]PhDE-2-DNA or 5,6-diMeCDE-DNA. DNA modified with 5,7-dimethylchryseneDE-2 (5,7-diMeCDE-2) and dibenzo[a,l]pyreneDE-2 (DB[a,l) PDE-2) required 20 and > 100-fold greater levels of adducts to give 50{\%} inhibition. Results with B[c]Ph, 5,6-diMeC, chrysene, 6-MeC and 5-MeC diol epoxide-2-DNA indicate that substitution of a methyl group in the vicinity of the bay-region of the PAH-molecule had limited effects on antigen recognition by this antiserum. However, the addition of a ring or methyl group remote from the diol epoxide moiety, as in DB[a,l] PDE-2-DNA or 5,7-diMeCDE-2-DNA greatly decreased antigen recognition. The ability of this antiserum to recognize DNA adducts of a particular class of polycyclic aromatic hydrocarbons will be useful for studies of their contribution to the DNA-binding that results from exposure to complex environmental mixtures.",
author = "Einolf, {Heidi J.} and Gross, {Maritha A.} and Butch, {Elizabeth R.} and Lin, {Jyh ming} and Shantu Amin and Haruhiko Yagi and Jerina, {Donald M.} and Baird, {William M.}",
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Selective recognition of substituted chrysene-diol epoxide-2-DNA adducts by antiserum prepared against DNA adducts of benzo[c]-phenanthrene-diol epoxide-2. / Einolf, Heidi J.; Gross, Maritha A.; Butch, Elizabeth R.; Lin, Jyh ming; Amin, Shantu; Yagi, Haruhiko; Jerina, Donald M.; Baird, William M.

In: Polycyclic Aromatic Compounds, Vol. 12, No. 2, 01.01.1997, p. 125-138.

Research output: Contribution to journalArticle

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AU - Einolf, Heidi J.

AU - Gross, Maritha A.

AU - Butch, Elizabeth R.

AU - Lin, Jyh ming

AU - Amin, Shantu

AU - Yagi, Haruhiko

AU - Jerina, Donald M.

AU - Baird, William M.

PY - 1997/1/1

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N2 - Polyclonal antiserum prepared against DNA that was modified with racemic benzo[c]phenanthrene-3,4-diol-1,2-epoxide-2 (B[c]PhDE-2; benzylic hydroxyl and epoxide oxygen trans) was characterized for specificity of antigen recognition. Previous studies have demonstrated that the antisera stereoselectively recognized B[c]PhDE-2-DNA and failed to recognize DNA modified with racemic benzo[c]phenanthrene-3,4-diol-1,2-epoxide-1 (B[c]PhDE-1-DNA, benzylic hydroxyl and epoxide oxygen cis), benzo[a]pyrene-7,8-diol-9, 10-epoxide-2-DNA (B[a]PDE-2-DNA) and 7,12-dimethylbenz-[a]anthracene-3,4-diol-1,2-epoxide-1-DNA (DMBADE-1-DNA). DNA samples modified by diol-epoxide-2 diastereomers of several hydrocarbons were tested in competitive ELISA assays utilizing B[c]PhDE-2-DNA (270 fmol adducts per well). DNA modified with racemic diol-epoxide-2 of various substituted chrysenes (including chrysene, benzo[g]chrysene (B[g]C), 6-methylchrysene (6-MeC), and 5-methychrysene (5-MeC), gave 50% inhibition of antisera binding at significantly higher concentrations (5 to 7-fold) than the parent B[c]PhDE-2-DNA or 5,6-diMeCDE-DNA. DNA modified with 5,7-dimethylchryseneDE-2 (5,7-diMeCDE-2) and dibenzo[a,l]pyreneDE-2 (DB[a,l) PDE-2) required 20 and > 100-fold greater levels of adducts to give 50% inhibition. Results with B[c]Ph, 5,6-diMeC, chrysene, 6-MeC and 5-MeC diol epoxide-2-DNA indicate that substitution of a methyl group in the vicinity of the bay-region of the PAH-molecule had limited effects on antigen recognition by this antiserum. However, the addition of a ring or methyl group remote from the diol epoxide moiety, as in DB[a,l] PDE-2-DNA or 5,7-diMeCDE-2-DNA greatly decreased antigen recognition. The ability of this antiserum to recognize DNA adducts of a particular class of polycyclic aromatic hydrocarbons will be useful for studies of their contribution to the DNA-binding that results from exposure to complex environmental mixtures.

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