SAC 92. Understanding chirality: how molecules that are mirror images of each other can act differently in the body

Cope, M. J.

doi:10.1039/ap9933000498

Cited by 8 publications

(18 citation statements)

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“…Therefore, when scientists aim to design molecules which would interact with biomolecules, they have to consider the asymmetrical structure of the targeted entity [12]. Indeed, in many cases, while one of the enantiomer of a molecule exhibits the desired biological activity (eutomer), the other could show no activity, even toxicity or antagonist effect [13]. For this reason, a US.…”

Section: Introductionmentioning

confidence: 99%

Cyclodextrin Derivatives as Chiral Supramolecular Receptors for Enantioselective Sensing

Shahgaldian

Pieles

2006

Sensors

122

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Abstract:In view of the chiral nature of many bio-molecules (and all bio-macromolecules), most of therapeutically active compounds which target these molecules need to be chiral and "good handed" to be effective. In addition to asymmetric synthetic and separation methodologies, enantioselective chemical sensors, able to distinguish between two enantiomers of the same molecule, are of relevance. In order to design these sensing tools, two major classes of enantioselective layers have been developed. The first is based on molecularly imprinted polymers which are produced (polymerized) in the presence of their target, thus the polymeric material keep in "memory" the size and the shape of this molecule and the system could be used for sensing (not reviewed here). The second approach makes use of sensitive layers containing chiral macrocyclic receptors able of stereoselective molecular recognition; these receptors are mainly based on cyclodextrins. In this contribution, are reviewed achievements in the use of native or chemically modified cyclodextrins for chiral sensing purposes (at interfaces). Potentialities of other chiral macrocycles based on calixarenes, calix-resorcinarenes or crown-ethers as supramolecular receptors for enantioselective sensing are discussed.

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Section: Introductionmentioning

confidence: 99%

Cyclodextrin Derivatives as Chiral Supramolecular Receptors for Enantioselective Sensing

Shahgaldian

Pieles

2006

Sensors

122

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“…One of the enantiomers can exhibit biological activity, whereas the other could show no activity, and even toxicity or antagonist effects. 1 In the last few years, a great interest in the separation and determination of optically active compounds has arisen. 2 Most of the studies are based on high performance liquid chromatography, electrochemiluminescence, capillary electrophoresis and gas chromatography.…”

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confidence: 99%

“…9 The cations studied were isoniazid and pyrazinamide, antibiotics for tuberculosis prevention and treatment. The anion [Co(C 2 B 9 H 11 ) 2 ] À , [1] À is a metallacarborane, Fig. 1(a).…”

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confidence: 99%

“…1(a). Some relevant properties of [1] À for ISEs have already been indicated, 9 but we wish to emphasize its lipophilicity, low charge density, 10 Conversely, short contacts are not so frequent with the widely used tetraphenylborate ISEs. With recent trends in ion sensing moving toward miniaturization, 11 it becomes apparent that the performance of these sensors depends on several factors, among them the stability of the redox inner couple that is, in its turn, highly influenced by the transport of ions or water through the membrane, an aspect related to the properties of the ion-exchanger.…”

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confidence: 99%

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Cobaltabisdicarbollide anion receptor for enantiomer-selective membrane electrodes

2009

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“…Therefore, it is of great interest to develop an efficient method to produce purer L-synephrine. Separation of synephrine and its metabolite has been accomplished by different methods such as capillary gas chromatography (8), and HPLC (9)(10)(11)(12). However, the only reported method to obtain highly pure natural L-synephrine is ion exchange resin technology (13) which is especially applicable to a large-volume production.…”

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confidence: 99%

Extraction of L-synephrine by Bis(2-ethylhexyl)phosphoric acid/n-octanol Reversed Micelles

Chen¹,

Li²,

Xu³

et al. 2012

Separation Science and Technology

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In this study, reversed micelles of Bis(2-ethylhexyl)phosphoric acid/n-octanol was prepared to investigate the purification of L-synephrine in Citrus aurantium fruit crude extract. The reverse micellar system formed was confirmed with atomic force microscopy and the effect of important factors on extraction efficiency, such as the pH of the aqueous phase, molar ratio of water to surfactant, surfactant concentration, cationic ion concentration, and extraction time, was studied. Under the optimal operational conditions, the purity of L-synephrine was improved to be >85% and the total yield >98%. Mathematic analysis and experimental results exhibited that the extraction process in this system was effectuated mainly via electrostatic interactions between L-synephrine and the surfactant.

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SAC 92. Understanding chirality: how molecules that are mirror images of each other can act differently in the body

Cited by 8 publications

References 0 publications

Cyclodextrin Derivatives as Chiral Supramolecular Receptors for Enantioselective Sensing

Cyclodextrin Derivatives as Chiral Supramolecular Receptors for Enantioselective Sensing

Cobaltabisdicarbollide anion receptor for enantiomer-selective membrane electrodes

Extraction of L-synephrine by Bis(2-ethylhexyl)phosphoric acid/n-octanol Reversed Micelles

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