Electrospray mass spectrometry and supramolecular complexes: quantifying the metal ion binding properties of cholic acid derivatives

Brady, Paul A.; Sanders, Jeremy K. M.

doi:10.1039/a800524i

Cited by 35 publications

(20 citation statements)

References 17 publications

(5 reference statements)

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“…The general trend observed was that the small ions favoured the formation of the large rings, whereas the addition of cesium shifted the distribution towards smaller rings [ 71 ]. Brady and Sanders have later quantified the metal ion binding properties of these cyclocholates and some monomeric bile acid derivatives by ESI mass spectroscopy [ 72 ]. They observed that ion-binding by the macrocyclic derivatives was markedly different from that by the monomers.…”

Section: Bile Acid-based Molecular and Supramolecular Assembliesmentioning

confidence: 99%

Bile Acids as Building Blocks of Supramolecular Hosts

2001

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Section: Bile Acid-based Molecular and Supramolecular Assembliesmentioning

confidence: 99%

Bile Acids as Building Blocks of Supramolecular Hosts

2001

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“…Binding constants were not measured; however, the relative affi nities of the amplifi ed cyclophane macrocycles for the different metal alkali were studied by electrospray ionization -mass spectrometry ( electrospray ionization ESI -mass spectrometry MS ), fi nding good agreement with the main amplifi cation observed. The yield of cyclic tetramer was increased by the addition of sodium in the cases of the " MEM " and di( p -methoxybenzyl) monomers, and these were found to bind sodium preferentially in the ESI -MS study [109] .…”

Section: Ensuring Meaningful Amplifi Cationsmentioning

confidence: 98%

“…The fi rst series of macrocyclic receptors generated using DCC were prepared by Sanders et al using transesterifi cation. Initial studies used building blocks based upon cholates functionalized with a methyl ester and a hydroxyl group (Scheme 3.5 ) [31,36,109] .…”

Section: Synthetic Receptors For Metal Cationsmentioning

confidence: 99%

Development of Synthetic Receptors using Dynamic Combinatorial Chemistry

Escalante

Furlán

2010

Dynamic Combinatorial Chemistry

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In order to bind a given guest, a receptor must be complementary -it must have recognition groups which are of the appropriate electronic character to complement the binding sites of the guest. Those recognition groups must be positioned on the receptor in a way that they can interact with recognition groups from the guest when both receptor and guest are in the binding conformation. Upon binding, the receptor and guest reorganize their interactions with solvent molecules (disrupting some and probably creating new ones), and change their conformation to achieve a suitable binding conformation. In the process, noncovalent interactions within each molecule may be broken or formed.The requirement to balance all the variables involved in this recognition process makes the design of successful synthetic receptors a signifi cant challenge.A frequently explored shortcut that facilitates receptor design is to incorporate rigidity in order to avoid as much as possible changes in conformation that are diffi cult to predict. In addition, a rigid preorganized receptor will decrease the cost of unfavorable reorganization energy. However, high -affi nity perfectly rigid receptors are not easy to achieve in practice since minor errors in design that demand readjustment from the receptor can be energetically very expensive [1] . Indeed, nature does not use rigidity to improve affi nity, but it still produces receptors with affi nities that are on average much better than the best synthetic receptors prepared to date. A recent survey of the binding effi ciency of synthetic and biological hosts by Houk et al. indicates that synthetic systems are typically several orders of magnitude less effi cient in binding small molecules than their biological counterparts [2] .Guest binding by natural receptors such as proteins is reinforced by intrareceptor interactions, which require conformational rearrangements of parts of the receptor that are very similar to the conformational rearrangement necessary to interact with the guest. Consequently the interactions that contribute to guest binding extend beyond the immediate binding site well into the protein structure [3] . Synthetic receptors that operate by the same principle will need to be able to Dynamic Combinatorial Chemistry. Edited by Joost N. H. Reek and Sijbren Otto

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“…Electrospray ionisation mass spectrometry was used for identifycation of non-covalent complexes. In present work, we have used mass spectrometry with electrospray ionization (ESI-MS) techniques to investigate guest-host compositions [8][9][10] in CTV complexes in samples processed with subcritical water at different temperatures. The existence of a guesthost complex can be confirmed by the presence of the peak of the host-guest complex in mass spectrum.…”

Section: Introductionmentioning

confidence: 99%

Mass Spectrometry Study of Non-Covalent Complexes of Bioflavonoids with Cyclotriveratrylene Synthesized in Subcritical Water

Lekar¹,

Borisenko²,

Vetrova³

et al. 2013

AJAC

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Mass spectrometry was used for studying of non-covalent complexes of bioflavonoids with cyclotriveratrylene (CVT). The complexes of cyclotriveratrylene (CVT) with the bioflavonoids (quercetin or dihydroquercetin) have been synthesized in subcritical water. The complexe formation was carried out at different temperatures of subcritical water (from 120˚C to 230˚C). The structure of the inclusion compounds was confirmed by the data of ESI MS spectroscopy. The mass spectrometry results showed the presence of mixed adducts of CTV monomer, dimer, trimer and tetramer with quercetin and dihydroquercetin. Composition of the CTV complexes with the bioflavonoids, which were obtained in subcritical water medium and by traditional method, was compared.

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Electrospray mass spectrometry and supramolecular complexes: quantifying the metal ion binding properties of cholic acid derivatives

Cited by 35 publications

References 17 publications

Bile Acids as Building Blocks of Supramolecular Hosts

Bile Acids as Building Blocks of Supramolecular Hosts

Development of Synthetic Receptors using Dynamic Combinatorial Chemistry

Mass Spectrometry Study of Non-Covalent Complexes of Bioflavonoids with Cyclotriveratrylene Synthesized in Subcritical Water

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