The relationship between ionization potential and horseradish peroxidase/hydrogen peroxide-catalyzed binding of aromatic hydrocarbons to DNA

Ercole L. Cavalieri; Eleanor G. Rogan; Robert W. Roth; Richard K. Saugier; Alaeddin Hakam

doi:10.1016/0009-2797(83)90150-3

The relationship between ionization potential and horseradish peroxidase/hydrogen peroxide-catalyzed binding of aromatic hydrocarbons to DNA

Ercole L. Cavalieri, Eleanor G. Rogan, Robert W. Roth, Richard K. Saugier, Alaeddin Hakam

Research output: Contribution to journal › Article › peer-review

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Abstract

The ionization potentials (IP) of 91 alternant polycyclic aromatic hydrocarbons (PAH) were determined from the absorption maximum of the chargetransfer complex of each hydrocarbon and chloranil in chloroform. The extent of horseradish peroxidase (HRP)-catalyzed binding to DNA of 14 hydrocarbons of varying IP was measured. Only hydrocarbons with IP < approx. 7.35eV were significantly bound to DNA. These results provide further evidence that HRP-mediated binding of PAH to DNA occurs by one-electron oxidation and indicate that hydrocarbons must have IP < approx. 7.35eV to be activated by one-electron oxidation. Thus, determination of IP and HRP-catalyzed binding to DNA can offer some guidelines for selecting aromatic hydrocarbons which might undergo carcinogenic activation by this mechanism.

Original language	English (US)
Pages (from-to)	87-109
Number of pages	23
Journal	Chemico-Biological Interactions
Volume	47
Issue number	1
DOIs	https://doi.org/10.1016/0009-2797(83)90150-3
State	Published - Oct 15 1983

Keywords

Carcinogenic activation
DNA binding
Horseradish peroxidase
Ionization potential
One-electron oxidation
Polycyclic aromatic hydrocarbons

ASJC Scopus subject areas

Toxicology

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10.1016/0009-2797(83)90150-3

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title = "The relationship between ionization potential and horseradish peroxidase/hydrogen peroxide-catalyzed binding of aromatic hydrocarbons to DNA",

abstract = "The ionization potentials (IP) of 91 alternant polycyclic aromatic hydrocarbons (PAH) were determined from the absorption maximum of the chargetransfer complex of each hydrocarbon and chloranil in chloroform. The extent of horseradish peroxidase (HRP)-catalyzed binding to DNA of 14 hydrocarbons of varying IP was measured. Only hydrocarbons with IP < approx. 7.35eV were significantly bound to DNA. These results provide further evidence that HRP-mediated binding of PAH to DNA occurs by one-electron oxidation and indicate that hydrocarbons must have IP < approx. 7.35eV to be activated by one-electron oxidation. Thus, determination of IP and HRP-catalyzed binding to DNA can offer some guidelines for selecting aromatic hydrocarbons which might undergo carcinogenic activation by this mechanism.",

keywords = "Carcinogenic activation, DNA binding, Horseradish peroxidase, Ionization potential, One-electron oxidation, Polycyclic aromatic hydrocarbons",

author = "Cavalieri, {Ercole L.} and Rogan, {Eleanor G.} and Roth, {Robert W.} and Saugier, {Richard K.} and Alaeddin Hakam",

note = "Funding Information: We wish to thank Drs. E. Boger, G. Daub, D. Nagel, M. Newman and D. Longfellow (NCI Repository) for kindly providing various PAH. We appreciate the expert editorial assistance of Ms. Mardelle Susman. This work was supported by NCI Contract NO1-CP-05620 and Grant 1 R01 CA25176 from the National Cancer Institute.",

year = "1983",

month = oct,

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doi = "10.1016/0009-2797(83)90150-3",

language = "English (US)",

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T1 - The relationship between ionization potential and horseradish peroxidase/hydrogen peroxide-catalyzed binding of aromatic hydrocarbons to DNA

AU - Cavalieri, Ercole L.

AU - Rogan, Eleanor G.

AU - Roth, Robert W.

AU - Saugier, Richard K.

AU - Hakam, Alaeddin

N1 - Funding Information: We wish to thank Drs. E. Boger, G. Daub, D. Nagel, M. Newman and D. Longfellow (NCI Repository) for kindly providing various PAH. We appreciate the expert editorial assistance of Ms. Mardelle Susman. This work was supported by NCI Contract NO1-CP-05620 and Grant 1 R01 CA25176 from the National Cancer Institute.

PY - 1983/10/15

Y1 - 1983/10/15

N2 - The ionization potentials (IP) of 91 alternant polycyclic aromatic hydrocarbons (PAH) were determined from the absorption maximum of the chargetransfer complex of each hydrocarbon and chloranil in chloroform. The extent of horseradish peroxidase (HRP)-catalyzed binding to DNA of 14 hydrocarbons of varying IP was measured. Only hydrocarbons with IP < approx. 7.35eV were significantly bound to DNA. These results provide further evidence that HRP-mediated binding of PAH to DNA occurs by one-electron oxidation and indicate that hydrocarbons must have IP < approx. 7.35eV to be activated by one-electron oxidation. Thus, determination of IP and HRP-catalyzed binding to DNA can offer some guidelines for selecting aromatic hydrocarbons which might undergo carcinogenic activation by this mechanism.

AB - The ionization potentials (IP) of 91 alternant polycyclic aromatic hydrocarbons (PAH) were determined from the absorption maximum of the chargetransfer complex of each hydrocarbon and chloranil in chloroform. The extent of horseradish peroxidase (HRP)-catalyzed binding to DNA of 14 hydrocarbons of varying IP was measured. Only hydrocarbons with IP < approx. 7.35eV were significantly bound to DNA. These results provide further evidence that HRP-mediated binding of PAH to DNA occurs by one-electron oxidation and indicate that hydrocarbons must have IP < approx. 7.35eV to be activated by one-electron oxidation. Thus, determination of IP and HRP-catalyzed binding to DNA can offer some guidelines for selecting aromatic hydrocarbons which might undergo carcinogenic activation by this mechanism.

KW - Carcinogenic activation

KW - DNA binding

KW - Horseradish peroxidase

KW - Ionization potential

KW - One-electron oxidation

KW - Polycyclic aromatic hydrocarbons

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The relationship between ionization potential and horseradish peroxidase/hydrogen peroxide-catalyzed binding of aromatic hydrocarbons to DNA

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