Structure–efficiency relationships of cyclodextrin scavengers in the hydrolytic degradation of organophosphorus compounds

• Sophie Letort,
• Michaël Bosco,
• Benedetta Cornelio,
• Frédérique Brégier,
• Sébastien Daulon,
• Géraldine Gouhier and
• François Estour

Beilstein J. Org. Chem. 2017, 13, 417–427, doi:10.3762/bjoc.13.45

• , cyclosarin or tabun (Figure 1) [23][24][25][26][27][28][29][30]. In fact, these β-CD derivatives play a dual role in this process: the macrocycle traps the organophosphorus whilst the bound α nucleophile reacts with the toxic agent leading to a non-toxic derivative. Other scavengers bearing several α

Interactions of cyclodextrins and their derivatives with toxic organophosphorus compounds

• Sophie Letort,
• Sébastien Balieu,
• William Erb,
• Géraldine Gouhier and
• François Estour

Beilstein J. Org. Chem. 2016, 12, 204–228, doi:10.3762/bjoc.12.23

• organophosphates is to be considered important insofar as the individual stereoisomers of a neurotoxic agent do not share the same level of toxicity [20]. Sarin (compounds 14a and 14b, Figure 5), cyclosarin (compounds 15a and 15b, Figure 5) and tabun (compounds 16a and 16b, Figure 5) consist of a mixture of two

• cyclosarin in presence of β-CD were then studied at 25 °C and pH 9 and also compared with the hydrolysis of soman. Their enantiomers are not degraded at the same rate, the P(R)-isomers of sarin and cyclosarin reacting faster than P(S)-isomers at pH 9 (Table 11). The different alkoxy substituents on the

• methylfluorophosphonates studied. After the complexation of P(R)-sarin, its phosphorus atom is located in the cavity above the level of the catalytically active hydroxy groups of β-CD, whereas for cyclosarin and soman, the phosphorus atoms lies in the plane of the hydroxy groups. The deep inclusion of P(R)-sarin into the

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, doi:10.3762/bjoc.7.182

• substituents with an aldoxime or a ketoxime moiety along the narrow opening of the β-cyclodextrin cavity was synthesized, and the ability of these compounds to reduce the inhibitory effect of the neurotoxic organophosphonate cyclosarin on its key target, acetylcholinesterase, was assessed in vitro. All

• compounds exhibited a larger effect than native β-cyclodextrin, and characteristic differences were noted. These differences in activity were correlated with the structural and electronic parameters of the substituents. In addition, the relatively strong effect of the cyclodextrin derivatives on cyclosarin

• degradation and, in particular, the observed enantioselectivity are good indications that noncovalent interactions between the cyclodextrin ring and the substrate, presumably involving the inclusion of the cyclohexyl moiety of cyclosarin into the cyclodextrin cavity, contribute to the mode of action. Among