Methyl Vinyl Ketone, a Toxic Ingredient in Cigarette Smoke Extract, Modifies Glutathione in Mouse Melanoma Cells

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  • Horiyama Shizuyo
    School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University
  • Takahashi Yuta
    School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University Department of Pharmacy, Gunma University Hospital
  • Hatai Mayuko
    School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University
  • Honda Chie
    School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University
  • Suwa Kiyoko
    School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University
  • Ichikawa Atsushi
    School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University
  • Yoshikawa Noriko
    School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University
  • Nakamura Kazuki
    School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University
  • Kunitomo Masaru
    School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University
  • Date Sachiko
    Riken Quantitative Biology Center, OLABB, Osaka University
  • Masujima Tsutomu
    Riken Quantitative Biology Center, OLABB, Osaka University
  • Takayama Mitsuo
    International Graduate School of Arts and Sciences, Yokohama City University

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Cigarette smoke contains many harmful chemicals, which contribute to the pathogenesis of smoking-related diseases such as chronic obstructive pulmonary disease, cancer and cardiovascular disease. The cytotoxicity of cigarette smoke is well documented, but the definitive mechanism behind its toxicity remains unknown. Ingredients in cigarette smoke are known to deplete intracellular glutathione (GSH), the most abundant cellular thiol antioxidant, and to cause oxidative stress. In the present study, we investigated the mechanism of cigarette smoke extract (CSE)-induced cytotoxicity in B16-BL6 mouse melanoma (B16-BL6) cells using liquid chromatography-tandem mass spectrometry. CSE and ingredients in cigarette smoke, methyl vinyl ketone (MVK) and crotonaldehyde (CA), reduced cell viability in a concentration-dependent manner. Also, CSE and the ingredients (m/z 70, each) irreversibly reacted with GSH (m/z 308) to form GSH adducts (m/z 378) in cells and considerably decreased cellular GSH levels at concentrations that do not cause cell death. Mass spectral data showed that the major product formed in cells exposed to CSE was the GSH-MVK adduct via Michael-addition and was not the GSH-CA adduct. These results indicate that MVK included in CSE reacts with GSH in cells to form the GSH-MVK adduct, and thus a possible reason for CSE-induced cytotoxicity is a decrease in intracellular GSH levels.

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