CSIRO Publishing blank image blank image blank image blank imageBooksblank image blank image blank image blank imageJournalsblank image blank image blank image blank imageAbout Usblank image blank image blank image blank imageShopping Cartblank image blank image blank image You are here: Journals > Environmental Chemistry   
Environmental Chemistry
Journal Banner
  Environmental problems - Chemical approaches
 
blank image Search
 
blank image blank image
blank image
 
  Advanced Search
   

Journal Home
About the Journal
Editorial Boards
Contacts
Content
Online Early
Current Issue
Just Accepted
All Issues
Special Issues
Research Fronts
Sample Issue
For Authors
General Information
Notice to Authors
Submit Article
Open Access
For Referees
Referee Guidelines
Review Article
For Subscribers
Subscription Prices
Customer Service

blue arrow e-Alerts
blank image
Subscribe to our Email Alert or RSS feeds for the latest journal papers.

red arrow Connect with us
blank image
facebook   youtube

 

Open Access Article << Previous     |     Next >>   Contents Vol 10(1)

Transformation of diphenylarsinic acid and related compounds in groundwater: production of thiol-containing arsenicals

Kunichika Nakamiya A B C, Mitsuha Yoshikane B, Hosoya Tomoko A and Yasuyuki Shibata A

A National Institute for Environmental Studies, Center for Environmental Measurement and Analysis, Onogawa 16-2, Tsukuba, Ibaraki 305-8506, Japan.
B Graduate School of Frontier Sciences, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, 277-8563 Chiba, Japan.
C Corresponding author. Email: nakamiya.kunichika@nies.go.jp

Environmental Chemistry 10(1) 17-21 http://dx.doi.org/10.1071/EN12110
Submitted: 30 July 2012  Accepted: 13 December 2012   Published: 27 February 2013


 
 Full Text
 PDF (414 KB)
 Export Citation
 Print
  

Environmental context. Contamination of groundwater by arsenic compounds used in chemical warfare research is a recently discovered environmental problem in Japan. We report evidence that the arsenic compounds originally present in the groundwater are transforming to thio-arsenic compounds of currently unknown environmental fate.

Abstract. During routine analyses of groundwater samples contaminated with diphenylarsinic acid (DPAA) at Kamisu, Ibaraki Prefecture, Japan, we obtained data indicating that unknown arsenic compounds accounted for up to 75 % of the total arsenic in some of the samples. Results from using liquid chromatography in combination with elemental mass spectrometry and tandem molecular mass spectrometry suggested that two of the main unknown peaks were diphenyldithioarsinic acid and methylphenyldithioarsinic acid. These assignments were later confirmed by comparison with chemically synthesised compounds. A potential transformation scheme for DPAA in the environment is proposed based on the derivatives identified in the environmental samples.



References

[1]  K. Ishii, A. Tamaoka, F. Otsuka, N. Iwasaki, K. Shin, A. Matsui, G. Endo, Y. Kumagai, T. Ishii, S. Shoji, T. Ogata, M. Ishizaki, M. Doi, N. Shimojo, Diphenylarsinic acid poisoning from chemical weapons in Kamisu, Japan Ann. Neurol. 2004, 56, 741.
CrossRef | CAS |

[2]  K. Nakamiya, Y. Shibata, H. Ito, J. S. Edmonds, M. Morita, Synthesis of phenyl arsenic analytical standards related to contaminated well water in Kamisu, Ibaraki, Japan Appl. Organomet. Chem. 2005, 19, 282.
CrossRef | CAS |

[3]  Y. Shibata, K. Tsuzuku, S. Komori, C. Umedzu, H. Imai, M. Morita, Analysis of diphenylarsinic acid in human and environmental samples by HPLC-ICP-MS Appl. Organomet. Chem. 2005, 19, 276.
CrossRef | CAS |

[4]  K. Kinoshita, Y. Shida, C. Sakuma, M. Ishizaki, K. Kiso, O. Shikino, H. Ito, M. Morita, T. Ochi, T. Kaise, Determination of diphenylarsinic acid and phenylarsonic acid, the degradation products of organoarsenic chemical warfare agents, in well water by HPLC-ICP-MS Appl. Organomet. Chem. 2005, 19, 287.
CrossRef | CAS |

[5]  T. Arao, Y. Maejima, K. Baba, Uptake of aromatic arsenicals from soil contaminated with diphenylarsinic acid by rice Environ. Sci. Technol. 2009, 43, 1097.
CrossRef | CAS |

[6]  S. Ueno, T. Kitamura, M. Nakamura, K. Ozone, Y. Shibata, M. Ishizaki, Determination of diphenylarsinic acid in plants and biological samples by HPLC/MS/MS using a stable isotope labeled compound Bunseki Kagaku 2006, 55, 41.
CrossRef | CAS |

[7]  T. Ochi, K. Kinoshita, T. Suzuki, K. Miyazaki, A. Noguchi, T. Kaise, The role of glutathione on the cytotoxic effects and cellular uptake of diphenylarsinic acid, a degradation product of chemical warfare agents Arch. Toxicol. 2006, 80, 486.
CrossRef | CAS |

[8]  K. Kita, T. Ochi, Down-regulation of glutaminase C in human hepatocarcinoma cell by diphenylarsinic acid, a degradation product of chemical warfare agents Toxicol. Appl. Pharmacol. 2007, 220, 262.
CrossRef | CAS |

[9]  Y. Kobayashi, T. Negishi, A. Mizumura, T. Watanabe, S. Hirano, Distribution and excretion of arsenic in cynomolgus monkey following repeated administration of diphenylarsinic acid Arch. Toxicol. 2008, 82, 553.
CrossRef | CAS |

[10]  R. Bentley, T. G. Chasteen, Microbial methylation of metalloids: arsenic, antimony, and bismuth Microbiol. Mol. Biol. Rev. 2002, 66, 250.
CrossRef | CAS |

[11]  W. R. Cullen, A. E. Erdman, B. C. McBride, A. W. Pickett, The identification of dimethylphenylarsine as a microbial metabolite using a simple method of chemofocusing J. Microbiol. Methods 1983, 1, 297.
CrossRef | CAS |

[12]  K. Nakamiya, T. Nakayama, H. Ito, J. S. Edmonds, Y. Shibata, M. Morita, Degradation of arylarsenic compounds by microorganisms FEMS Micro. Boil. Lett. 2007, 274, 184.
CrossRef | CAS |

[13]  D. Wallschläger, J. London, Determination of methylated arsenic–sulfur compounds in groundwater Environ. Sci. Technol. 2008, 42, 228.
CrossRef |

[14]  R. A. Diaz-Bone, T. Van de Wiele, Biotransformation of metal(loid)s by intestinal microorganisms Pure Appl. Chem. 2010, 82, 409.
CrossRef | CAS |

[15]  A. Müller, P. Werle, Darstellung, Elektronen- und Schwingungsspektren von Kaliumdiphenyldithioarsinat und Phenyldithioarsinato-komplexen Chem. Ber. 1971, 104, 3782.
CrossRef |

[16]  G. Brauer, Hydrogen sulfide, in Handbook of Preparative Inorganic Chemistry 1963, pp. 344–346 (Academic Press Inc. Ltd: London).

[17]  J. S. Edmonds, T. Nakayama, T. Kondo, M. Morita, Diasteoisomerism of thiol complexes of arsenic acids and pseudoasymmetry of arsenic: a 1H and 13C NMR study Magn. Reson. Chem. 2006, 44, 151.
CrossRef | CAS |


   
 
    
Legal & Privacy | Contact Us | Help

CSIRO

© CSIRO 1996-2013