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Identification of a N 7-guanine adduct of 1-bromopropane in calf thymus DNA by mass spectrometry

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Abstract

As a replacement for chlorofluorocarbons that cause ozone depletion, 1-bromopropane has been widely used in work place. In the present study, the formation of N 7-guanine adduct in DNA by 1-bromopropane was evaluated in vitro to elucidate the possible mechanism of its toxic action. N 7-Propyl guanine was chemically synthesized and structurally characterized by NMR, UV, HPLC, and liquid chromatographyelectrospray ionization mass spectrometry (LC- ESI MS) for using as a reference standard. An incubation of 2ʹ-deoxyguanosine with 1-bromopropane produced N 7-propyl adduct, which was identified by UV, HPLC and ESI-MS. In addition, N7-guanine adduct was also identified from the incorporation of calf thymus DNA with 1-bromopropane at the physiological condition by LC-ESI MS. Furthermore, the production of adduct was proportional to the amounts of 1-bromopropane used. These results indicated that the molecular mechanism underlying toxic effects of 1-bromopropane would be associated with the adduct formation on DNA at least in part.

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Authors and Affiliations

  1. College of Pharmacy, Yeungnam University, Gyeongsan, Korea

    Pritam Thapa, Eun-Kyung Kim, Mahesh Raj Nepal, Ki Sun Jeong, Mi Jeong Kang, Keumhan Noh, Tae Cheon Jeong & Eung-Seok Lee

  2. College of Pharmacy, Kyungpook National University, Daegu, Korea

    Sangkyu Lee

  3. College of Pharmacy, Chungnam National University, Daejeon, Korea

    Hye Gwang Jeong

  4. Department of Emergency Medical Technology, Daejeon University, Daejeon, Korea

    Jun-Ho Lee

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  1. Pritam Thapa
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  2. Eun-Kyung Kim
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  3. Mahesh Raj Nepal
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  4. Ki Sun Jeong
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  5. Mi Jeong Kang
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  6. Keumhan Noh
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  7. Sangkyu Lee
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  8. Hye Gwang Jeong
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  9. Jun-Ho Lee
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  10. Tae Cheon Jeong
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Correspondence to Tae Cheon Jeong or Eung-Seok Lee.

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Thapa, P., Kim, EK., Nepal, M.R. et al. Identification of a N 7-guanine adduct of 1-bromopropane in calf thymus DNA by mass spectrometry. Mol. Cell. Toxicol. 12, 7–14 (2016). https://doi.org/10.1007/s13273-016-0002-5

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  • DOI: https://doi.org/10.1007/s13273-016-0002-5

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