Highly efficient cyclosarin degradation mediated by a β-cyclodextrin derivative containing an oxime-derived substituent

Michael Zengerle, Florian Brandhuber, Christian Schneider, Franz Worek, Georg Reiter and Stefan Kubik
Beilstein J. Org. Chem. 2011, 7, 1543–1554. https://doi.org/10.3762/bjoc.7.182

Supporting Information

Supporting Information File 1: Detailed experimental procedures and physical data for all newly prepared compounds.
Format: PDF Size: 163.6 KB Download

Cite the Following Article

Highly efficient cyclosarin degradation mediated by a β-cyclodextrin derivative containing an oxime-derived substituent
Michael Zengerle, Florian Brandhuber, Christian Schneider, Franz Worek, Georg Reiter and Stefan Kubik
Beilstein J. Org. Chem. 2011, 7, 1543–1554. https://doi.org/10.3762/bjoc.7.182

How to Cite

Zengerle, M.; Brandhuber, F.; Schneider, C.; Worek, F.; Reiter, G.; Kubik, S. Beilstein J. Org. Chem. 2011, 7, 1543–1554. doi:10.3762/bjoc.7.182

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Lau, E. Y.; Enright, H. A.; Lao, V.; Malfatti, M. A.; Mayer, B. P.; Williams, A. M.; Valdez, C. A. Evaluation of 6-OxP-CD, an Oxime-based cyclodextrin as a viable medical countermeasure against nerve agent poisoning: Experimental and molecular dynamic simulation studies on its inclusion complexes with cyclosarin, soman and VX. PloS one 2023, 18, e0283181. doi:10.1371/journal.pone.0283181
  • Braga Barbosa, C.; Gaß, P.; Hamsch, D. J.; Kubik, S. Characterization of the Interaction of Nerve Agent Mimics with Selected Synthetic Receptors. Organic Materials 2022, 4, 146–152. doi:10.1055/a-1939-6455
  • Liu, P.; Wang, H.; Zeng, H.; Hong, X.; Huang, F. A [15]paracyclophenone and its fluorenone-containing derivatives: syntheses and binding to nerve agent mimics via aryl-CH hydrogen bonding interactions. Organic Chemistry Frontiers 2021, 8, 25–31. doi:10.1039/d0qo00456a
  • Andrae, B.; Bauer, D.; Gaß, P.; Koller, M.; Worek, F.; Kubik, S. Influence of cyclic and acyclic cucurbiturils on the degradation pathways of the chemical warfare agent VX. Organic & biomolecular chemistry 2020, 18, 5218–5227. doi:10.1039/d0ob01167c
  • Amend, N.; Niessen, K. V.; Seeger, T. F.; Wille, T.; Worek, F.; Thiermann, H. Diagnostics and treatment of nerve agent poisoning—current status and future developments. Annals of the New York Academy of Sciences 2020, 1479, 13–28. doi:10.1111/nyas.14336
  • Liu, W.-E.; Chen, Z.; Yang, L.-P.; Au-Yeung, H. Y.; Jiang, W. Molecular recognition of organophosphorus compounds in water and inhibition of their toxicity to acetylcholinesterase. Chemical communications (Cambridge, England) 2019, 55, 9797–9800. doi:10.1039/c9cc04603h
  • Timperley, C. M.; Abdollahi, M.; Al-Amri, A. S.; Baulig, A.; Benachour, D.; Borrett, V.; Cariño, F. A.; Geist, M.; Gonzalez, D.; Kane, W.; Kovarik, Z.; Martínez-Álvarez, R.; Mourão, N. M. F.; Neffe, S.; Raza, S. K.; Rubaylo, V.; Suárez, A. G.; Takeuchi, K.; Tang, C.; Trifiro, F.; van Straten, F. M.; Vanninen, P.; Vucinic, S.; Zaitsev, V.; Zafar-Uz-Zaman, M.; Zina, M. S.; Holen, S.; Forman, J. E.; Alwan, W. S.; Suri, V. Advice on assistance and protection from the Scientific Advisory Board of the Organisation for the Prohibition of Chemical Weapons: Part 2. On preventing and treating health effects from acute, prolonged, and repeated nerve agent exposure, and the identification of medical countermeasures able to reduce or eliminate the longer term health effects of nerve agents. Toxicology 2018, 413, 13–23. doi:10.1016/j.tox.2018.11.009
  • Border, S. E.; Pavlović, R. Z.; Zhiquan, L.; Badjić, J. D. Removal of Nerve Agent Simulants from Water Using Light-Responsive Molecular Baskets. Journal of the American Chemical Society 2017, 139, 18496–18499. doi:10.1021/jacs.7b11960
  • Kubik, S. Gegenmittel bei Vergiftungen mit chemischen Kampfstoffen. Nachrichten aus der Chemie 2017, 65, 766–771. doi:10.1002/nadc.20174058200
  • Letort, S.; Bosco, M.; Cornelio, B.; Brégier, F.; Daulon, S.; Gouhier, G.; Estour, F. Structure-efficiency relationships of cyclodextrin scavengers in the hydrolytic degradation of organophosphorus compounds. Beilstein journal of organic chemistry 2017, 13, 417–427. doi:10.3762/bjoc.13.45
  • Bierwisch, A.; Koller, M.; Worek, F.; Kubik, S. Pathways for the Reactions Between Neurotoxic Organophosphorus Compounds and Oximes or Hydroxamic Acids. European Journal of Organic Chemistry 2016, 2016, 5831–5838. doi:10.1002/ejoc.201601053
  • Hiscock, J. R.; Wells, N. J.; Ede, J. A.; Gale, P. A.; Sambrook, M. R. Biasing hydrogen bond donating host systems towards chemical warfare agent recognition. Organic & biomolecular chemistry 2016, 14, 9560–9567. doi:10.1039/c6ob01210h
  • Schneider, C.; Bierwisch, A.; Koller, M.; Worek, F.; Kubik, S. Entgiftung von VX und anderen V‐Stoffen in Wasser bei 37 °C und pH 7.4 durch substituierte Sulfonatocalix[4]arene. Angewandte Chemie 2016, 128, 12859–12863. doi:10.1002/ange.201606881
  • Schneider, C.; Bierwisch, A.; Koller, M.; Worek, F.; Kubik, S. Detoxification of VX and Other V-Type Nerve Agents in Water at 37 °C and pH 7.4 by Substituted Sulfonatocalix[4]arenes. Angewandte Chemie (International ed. in English) 2016, 55, 12668–12672. doi:10.1002/anie.201606881
  • Worek, F.; Thiermann, H.; Wille, T. Oximes in organophosphate poisoning: 60 years of hope and despair. Chemico-biological interactions 2016, 259, 93–98. doi:10.1016/j.cbi.2016.04.032
  • Letort, S.; Balieu, S.; Erb, W.; Gouhier, G.; Estour, F. Interactions of cyclodextrins and their derivatives with toxic organophosphorus compounds. Beilstein journal of organic chemistry 2016, 12, 204–228. doi:10.3762/bjoc.12.23
  • Harvey, D. Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: An update for 2011-2012. Mass spectrometry reviews 2015, 36, 255–422. doi:10.1002/mas.21471
  • Kranawetvogl, A.; Müller, S.; Kubik, S.; Spruit, H. E.; Thiermann, H.; Worek, F.; Noort, D.; Reiter, G. Elimination kinetics and molecular reaction mechanisms of cyclosarin (GF) by an oxime substituted β-cyclodextrin derivative in vitro. Toxicology letters 2015, 239, 41–52. doi:10.1016/j.toxlet.2015.08.007
  • Singh, N.; Karpichev, Y.; Tiwari, A. K.; Kuca, K.; Ghosh, K. K. Oxime functionality in surfactant self-assembly: An overview on combating toxicity of organophosphates. Journal of Molecular Liquids 2015, 208, 237–252. doi:10.1016/j.molliq.2015.04.010
  • Worek, F.; Thiermann, H.; Wille, T. Catalytic bioscavengers in nerve agent poisoning: A promising approach?. Toxicology letters 2015, 244, 143–148. doi:10.1016/j.toxlet.2015.07.012
Other Beilstein-Institut Open Science Activities