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Involvement of Semiquinone Radicals in the in Vitro Cytotoxicity of Cigarette Mainstream Smoke

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    Article

    Involvement of Semiquinone Radicals in the in Vitro Cytotoxicity of Cigarette Mainstream Smoke
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    Philip Morris USA Research Center, 4201 Commerce Road, Richmond, Virginia 23234, Philip Morris Research Laboratories GmbH, Fuggerstrasse 3, D-51149 Cologne, Germany, and 58 Chapman Way, St. Neots, PE19 2HD U.K.
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    Chemical Research in Toxicology

    Cite this: Chem. Res. Toxicol. 2006, 19, 12, 1602–1610
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    https://doi.org/10.1021/tx060162u
    Published December 1, 2006
    Copyright © 2006 American Chemical Society
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    Abstract

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    Free radicals in cigarette smoke have attracted a great deal of attention because they are hypothesized to be responsible in part for several of the pathologies related to smoking. Hydroquinone, catechol, and their methyl-substituted derivatives are abundant in the particulate phase of cigarette smoke, and they are known precursors of semiquinone radicals. In this study, the in vitro cytotoxicity of these dihydroxybenzenes was determined using the neutral red uptake (NRU) assay, and their radical-forming capacity was determined by electron paramagnetic resonance (EPR). All of the dihydroxybenzenes studied were found to generate appreciable amounts of semiquinone radicals when dissolved in the cell culture medium employed in the NRU assay. Hydroquinone exhibited by far the highest capacity to form semiquinone radicals at physiological pH, even though it is not the most cytotoxic dihydroxybenzene. Methyl-substituted dihydroxybenzenes were found to be more cytotoxic than either hydroquinone or catechol. The formation of semiquinone radicals via auto-oxidation of the dihydroxybenzenes was found to be dependent on the reduction potential of the corresponding quinone/semiquinone radical redox couple. The capacity to generate semiquinone radicals was found to be insufficient to explain the variance in the cytotoxicity among the dihydroxybenzenes in our study; consequently, other mechanisms of toxicity must also be involved. The observed interactions between 2,6-dimethylhydroquinone and hydroquinone in the cytotoxicity assay and EPR analysis suggest that care needs to be taken when the bioactivity of cigarette smoke constituents is evaluated, i.e., the effect of the cigarette smoke complex matrix on the activity of the single constituent studied must be taken into consideration.

    Copyright © 2006 American Chemical Society

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     Corresponding author. E-mail:  [email protected]. Phone:  804-274-3937. Fax:  804-274-2576.

    †

     Philip Morris USA Research Center.

    ‡

     Philip Morris Research Laboratories GmbH.

    §

     58 Chapman Way.

    Cited By

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    Chemical Research in Toxicology

    Cite this: Chem. Res. Toxicol. 2006, 19, 12, 1602–1610
    Click to copy citationCitation copied!
    https://doi.org/10.1021/tx060162u
    Published December 1, 2006
    Copyright © 2006 American Chemical Society
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