@article{TaleshiSeidlerEgdalJensenetal.2014,
  author    = {Taleshi, Mojtaba S. and Seidler-Egdal, Rune K. and Jensen, Kenneth Bendix and Schwerdtle, Tanja and Francesconi, Kevin A.},
  title     = {Synthesis and Characterization of Arsenolipids: Naturally Occurring Arsenic Compounds in Fish and Algae},
  series = {Organometallics},
  volume    = {33},
  journal   = {Organometallics},
  number    = {6},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0276-7333},
  doi       = {10.1021/om4011092},
  pages     = {1397 -- 1403},
  year      = {2014},
  abstract  = {Arsenic-containing lipids (arsenolipids) are natural products present in fish and algae. Because these compounds occur in foods, there is considerable interest in their human toxicology. We report the synthesis and characterization of seven arsenic-containing lipids, including six natural products. The compounds comprise dimethylarsinyl groups attached to saturated long-chain hydrocarbons (three compounds), saturated long-chain fatty acids (two compounds), and monounsaturated long chain fatty acids (two compounds). The arsenic group was introduced through sodium dimethylarsenide or bis(dimethylarsenic) oxide. The latter route provided higher and more reproducible yields, and consequently, this pathway was followed to synthesize six of the seven compounds. Mass spectral properties are described to assist in the identification of these compounds in natural samples. The pure synthesized arsenolipids will be used for in vitro experiments with human cells to test their uptake, biotransformation, and possible toxic effects.},
  language  = {en}
}
@misc{MeyerSchulzJeibmannetal.2014,
  author    = {Meyer, S{\"o}ren and Schulz, Jacqueline and Jeibmann, Astrid and Taleshi, Mojtaba S. and Ebert, Franziska and Francesconi, Kevin and Schwerdtle, Tanja},
  title     = {Arsenic-containing hydrocarbons are toxic in the in vivo model Drosophila melanogaster},
  volume    = {11},
  number    = {6},
  url       = {http://nbn-resolving.de/urn:nbn:de:kobv:517-opus4-76819},
  pages     = {2010 -- 2014},
  year      = {2014},
  abstract  = {Arsenic-containing hydrocarbons (AsHC) constitute one group of arsenolipids that have been identified in seafood. In this first in vivo toxicity study for AsHCs, we show that AsHCs exert toxic effects in Drosophila melanogaster in a concentration range similar to that of arsenite. In contrast to arsenite, however, AsHCs cause developmental toxicity in the late developmental stages of Drosophila melanogaster. This work illustrates the need for a full characterisation of the toxicity of AsHCs in experimental animals to finally assess the risk to human health related to the presence of arsenolipids in seafood.},
  language  = {en}
}
@article{MeyerSchulzJeibmannetal.2014,
  author    = {Meyer, S{\"o}ren and Schulz, Jacqueline and Jeibmann, Astrid and Taleshi, Mojtaba S. and Ebert, Franziska and Francesconi, Kevin and Schwerdtle, Tanja},
  title     = {Arsenic-containing hydrocarbons are toxic in the in vivo model Drosophila melanogaster},
  series = {Metallomics},
  journal   = {Metallomics},
  editor    = {Schwerdtle, Tanja},
  publisher = {The Royal Society of Chemistry},
  address   = {Cambridge},
  issn      = {1756-5901},
  pages     = {2010 -- 2014},
  year      = {2014},
  abstract  = {Arsenic-containing hydrocarbons (AsHC) constitute one group of arsenolipids that have been identified in seafood. In this first in vivo toxicity study for AsHCs, we show that AsHCs exert toxic effects in Drosophila melanogaster in a concentration range similar to that of arsenite. In contrast to arsenite, however, AsHCs cause developmental toxicity in the late developmental stages of Drosophila melanogaster. This work illustrates the need for a full characterisation of the toxicity of AsHCs in experimental animals to finally assess the risk to human health related to the presence of arsenolipids in seafood.},
  language  = {en}
}
@article{MeyerRaberEbertetal.2015,
  author    = {Meyer, S{\"o}ren and Raber, Georg and Ebert, Franziska and Taleshi, Mojtaba S. and Francesconi, Kevin A. and Schwerdtle, Tanja},
  title     = {Arsenic-containing hydrocarbons and arsenic-containing fatty acids: Transfer across and presystemic metabolism in the Caco-2 intestinal barrier model},
  series = {Molecular nutrition \& food research : bioactivity, chemistry, immunology, microbiology, safety, technology},
  volume    = {59},
  journal   = {Molecular nutrition \& food research : bioactivity, chemistry, immunology, microbiology, safety, technology},
  number    = {10},
  publisher = {Wiley-Blackwell},
  address   = {Hoboken},
  issn      = {1613-4125},
  doi       = {10.1002/mnfr.201500286},
  pages     = {2044 -- 2056},
  year      = {2015},
  abstract  = {Scope: Arsenic-containing hydrocarbons (AsHCs) and arsenic-containing fatty acids (AsFAs) represent two classes of arsenolipids occurring naturally in marine food. Toxicological data are yet scarce and an assessment regarding the risk to human health has not been possible. Here, we investigated the transfer and presystemic metabolism of five arsenolipids in an intestinal barrier model. Methods and results: Three AsHCs and two AsFAs were applied to the Caco-2 intestinal barrier model. Thereby, the short-chain AsHCs reached up to 50\% permeability. Transport is likely to occur via passive diffusion. The AsFAs showed lower intestinal bioavailability, but respective permeabilities were still two to five times higher as compared to arsenobetaine or arsenosugars. Interestingly, AsFAs were effectively biotransformed while passing the in vitro intestinal barrier, whereas AsHCs were transported to the blood-facing compartment essentially unchanged. Conclusion: AsFAs can be presystemically metabolised and the amount of transferred arsenic is lower than that for AsHCs. In contrast, AsHCs are likely to be highly intestinally bioavailable to humans. Since AsHCs exert strong toxicity in vitro and in vivo, toxicity studies with experimental animals as well as a human exposure assessment are needed to assess the risk to human health related to the presence of AsHCs in seafood.},
  language  = {en}
}