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

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• 作者：Pritam Thapa ; Eun-Kyung Kim ; Mahesh Raj Nepal…
• 关键词：1 ; Bromopropane ; N 7 ; Propyl guanine ; In vitro ; Calf thymus DNA ; Adduct formation
• 刊名：Molecular & Cellular Toxicology
• 出版年：2016
• 出版时间：March 2016
• 年：2016
• 卷：12
• 期：1
• 页码：7-14
• 全文大小：1,569 KB
• 参考文献：1.Takeuchi, Y., Ichihara, G. & Kamijima, M. A review on toxicity of 2
  omopropane: mainly on its reproductive toxicity. J Occup Health 39:179–191 (1997).CrossRef
  2.Kim, Y. et al. Hematopoietic and reproductive hazards o Korean electronic workers exposed to solvents containing 2
  omopropane. Scand J Work Environ Health 39:387–391 (1996).CrossRef
  3.Park, J. S. et al. An outbreak of hematopoietic and reproductive disorders due to solvents containing 2
  omopropane in an electronic factory South Korea: epidemiological survey. J Occup Health 39:138–143 (1997).CrossRef
  4.Yu, I. J. et al. The occupational exposure level (OEL) for 2
  omopropane: the first OEL established by Korea. Appl Occup Environ Hyg 14:356–358 (1999).CrossRef PubMed
  5.Maeng, S. H. & Yu, I. J. Mutagenicity of 2
  omopropane. Ind Health 35:87–95 (1997).CrossRef PubMed
  6.Ichihara, G. Neuro-reproductive toxicities of 1
  omopropane and 2
  omopropane. Int Arch Occup Environ Health 78:79–96 (2005).CrossRef PubMed
  7.Barber, E. D., Donish, W. H. & Mueller, K. R. A procedure for the quantitative measurement of the mutagenicity of volatile liquids in th Ames Salmonella/ microsome assay. Mutat Res 90:31–48 (1981).CrossRef PubMed
  8.Lee, S. K. et al. Role of glutathione conjugation in the hepatotoxicity and immunotoxicity induced by 1
  omopropane in female BALB/c mice. J Appl Toxicol 27:358–367 (2007).CrossRef PubMed
  9.Sekiguchi, S., Suda, M., Zhai, Y. L. & Honma, T. Effects of 1
  omopropane, 2
  omopropane, and 1,2-dichloropropane on the estrous cycle and ovulation in F344 rats. Toxicol Lett 126:41–49 (2002).CrossRef PubMed
  10.Zhao, L. X. et al. Synthesis, characterization and in vitro identification of N7-guanine adduct of 2
  omopropane. Arch Pharm Res 25:39–44 (2002).CrossRef PubMed
  11.Yu, X. et al. Neurotoxicity of 2
  omopropane and 1
  omopropane, alternative solvents for chlorofluorocarbons. Environ Res 85:48–52 (2001).CrossRef PubMed
  12.Thapa, P. et al. Depurination of dA and dG induced by 2
  omopropane at the physiological condition. J Appl Pharmacol 15:224–229 (2007).CrossRef
  13.Sherchan, J., Choi, H. & Lee, E. S. Depurination of nucleosides and calf thymus DNA induced by 2
  omopropane at the physiological condition. Bull Korean Chem Soc 30:2309–2317 (2009).CrossRef
  14.Lee, S. K. et al. Hepatotoxic effect of 1
  omopropane and its conjugation with glutathione in male ICR mice. Arch Pharm Res 28:1177–1182 (2005).CrossRef PubMed
  15.Han, E. H. et al. 1-Bromopropane up-regulates cyclooxygenase-2 expression via NF-κB and C/EBP activation in murine macrophages. Food Chem Toxicol 50:1616–1622 (2012).CrossRef PubMed
  16.Kim, D. H. & Guengerich, F. P. Formation of the DNA adduct S-[2-(N7-guanyl)ethyl]glutathione from ethylene dibromide: effects of modulation of glutathione and glutathione S-transferase levels and lack of a role for sulfation. Carcinogenesis 11:419–424 (1990).CrossRef PubMed
  17.Kim, D. H., Humphreys, W. G. & Guengerich, F. P. Characterization of S-[2-(N1-adenyl)ethyl]glutathione as an adduct formed in RNA and DNA from 1,2-dibromoethane. Chem Res Toxicol 3:587–594 (1990).CrossRef PubMed
  
• 作者单位：Pritam Thapa (1)
  Eun-Kyung Kim (1)
  Mahesh Raj Nepal (1)
  Ki Sun Jeong (1)
  Mi Jeong Kang (1)
  Keumhan Noh (1)
  Sangkyu Lee (2)
  Hye Gwang Jeong (3)
  Jun-Ho Lee (4)
  Tae Cheon Jeong (1)
  Eung-Seok Lee (1)
  
  1. College of Pharmacy, Yeungnam University, Gyeongsan, Korea
  2. College of Pharmacy, Kyungpook National University, Daegu, Korea
  3. College of Pharmacy, Chungnam National University, Daejeon, Korea
  4. Department of Emergency Medical Technology, Daejeon University, Daejeon, Korea
  
• 刊物主题：Cell Biology; Pharmacology/Toxicology;
• 出版者：Springer Netherlands
• ISSN：2092-8467

文摘

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.