Detoxification of tabun at physiological pH mediated by substituted β-cyclodextrin and glucose derivatives containing oxime groups

Brandhuber, Florian; Zengerle, Michael; Porwol, Luzian; Tenberken, Oliver; Thiermann, Horst; Worek, Franz; Kubik, Stefan; Reiter, Georg

doi:10.1016/j.tox.2012.08.013

Cited by 22 publications

(15 citation statements)

References 53 publications

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“…If 20b was the most efficient compound for the cyclosarin detoxification of this pyridinium series, Kubik et al showed that 20c was more efficient for the degradation of tabun ( Scheme 4 ) [ 80 ]. However, it should be pointed out that a simple glucose derivative bearing the same nucleophilic group has a similar activity.…”

Section: Reviewmentioning

confidence: 99%

“…Efficiency of compounds 23a–i against chemical warfare agents: Amongst the derivatives 23a – i with the pyridine aldoxime linked to the CD by a triazole ring, compound 23a is the most interesting scavenger. To access more potent compounds, Kubik et al later introduced two α-nucleophiles on A and D units of β-CD [ 80 ]. Surprisingly, only a slight increase of the activity against tabun compared to that of 20b was noticed.…”

Section: Reviewmentioning

confidence: 99%

“…The 3-monosubstituted derivative 41 was successfully obtained starting from the partially-protected 2,6-dimethyl-β-CD ( Scheme 7 ) [ 88 ]. Finally, CDs bearing an oxime ( 36 and 39a ) or a hydroxamic acid ( 39b ) group in position 3 were prepared as previously described via an azide–alkyne cycloaddition ( Scheme 7 ) [ 76 , 80 ].…”

Section: Reviewmentioning

confidence: 99%

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Interactions of cyclodextrins and their derivatives with toxic organophosphorus compounds

Letort¹,

Balieu²,

Erb³

et al. 2016

Beilstein J. Org. Chem.

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SummaryThe aim of this review is to provide an update on the current use of cyclodextrins against organophosphorus compound intoxications. Organophosphorus pesticides and nerve agents play a determinant role in the inhibition of cholinesterases. The cyclic structure of cyclodextrins and their toroidal shape are perfectly suitable to design new chemical scavengers able to trap and hydrolyze the organophosphorus compounds before they reach their biological target.

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Section: Reviewmentioning

confidence: 99%

Section: Reviewmentioning

confidence: 99%

See 1 more Smart Citation

Interactions of cyclodextrins and their derivatives with toxic organophosphorus compounds

Letort¹,

Balieu²,

Erb³

et al. 2016

Beilstein J. Org. Chem.

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show abstract

“…3 A -Azido-3 A -deoxy-allo--CD was synthesised through a the substitution reaction from 3 A -O-(naphthyl-2-sulfonyl)--CD, [130] whereas 3 A -azido-3 A -deoxy-altro--or -γ-CD were synthesised by opening of the corresponding 2 A ,3 Amanno-epoxy CD derivatives (Scheme 10). 3 A -Azido-3 A -deoxy-allo--CD was synthesised through a the substitution reaction from 3 A -O-(naphthyl-2-sulfonyl)--CD, [130] whereas 3 A -azido-3 A -deoxy-altro--or -γ-CD were synthesised by opening of the corresponding 2 A ,3 Amanno-epoxy CD derivatives (Scheme 10).…”

Section: Synthesis Of Derivatives Substituted At Positionmentioning

confidence: 99%

Monosubstituted Cyclodextrins as Precursors for Further Use

Řezanka

2016

Eur J Org Chem

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Cyclodextrin derivatives find use in a broad field of applications (e.g., nanomaterials, biomedical applications, catalysis, separation techniques, sensors etc.), with monosubstitution allowing cyclodextrins to be attached to various types of surfaces or for a new feature to be introduced onto a cyclodextrin skeleton (recognition, catalysis, …). Although an enormous number of monosubstituted cyclodextrin derivatives have been synthesised, this review focuses only on the synthesis of several interesting monosubstituted derivatives (allyl, cinnamyl, propargyl, formylmethyl, carboxymethyl, azido and amino) suitable for further modifications. These derivatives allow the synthesis of an unlimited number of desired cyclodextrin derivatives. Using a cyclodextrin derivative already monosubstituted with a suitable functional group is much easier than the optimisation of monosubstitution for every new cyclodextrin derivative desired.

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“…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 nucleophilic groups were described [31–32]. …”

Section: Introductionmentioning

confidence: 99%

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

Letort¹,

Bosco²,

Cornelio³

et al. 2017

Beilstein J. Org. Chem.

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New derivatives of cyclodextrins were prepared in order to determine the relative importance of the structural key elements involved in the degradation of organophosphorus nerve agents. To avoid a competitive inclusion between the organophosphorus substrate and the iodosobenzoate group, responsible for its degradation, the latter group had to be covalently bound to the cyclodextrin scaffold. Although the presence of the α nucleophile iodosobenzoate was a determinant in the hydrolysis process, an imidazole group was added to get a synergistic effect towards the degradation of the agents. The degradation efficiency was found to be dependent on the relative position of the heterocycle towards the reactive group as well as on the nature of the organophosphorus derivative.

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Detoxification of tabun at physiological pH mediated by substituted β-cyclodextrin and glucose derivatives containing oxime groups

Cited by 22 publications

References 53 publications

Interactions of cyclodextrins and their derivatives with toxic organophosphorus compounds

Interactions of cyclodextrins and their derivatives with toxic organophosphorus compounds

Monosubstituted Cyclodextrins as Precursors for Further Use

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

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