Binding of acetylcholine and other quaternary ammonium cations by sulfonated calixarenes. Crystal structure of a [choline-tetrasulfonated calix[4]arene] complex

Lehn, Jean‐Maríe; Méric, Robert; Vigneron, Jean‐Pierre; Césario, Michèle; Guilhem, Jean; Pascard, Claudine; Asfari, Zouhair; Vicens, Jacques

doi:10.1080/10610279508029480

Cited by 148 publications

(132 citation statements)

References 27 publications

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“…Thus, the (13) where m c , m a and m s are the atomic masses of the cations, anions, and solvent respectively. Therefore, the electrochemical impedance, E ( ) I , which is measured, is equal to:…”

Section: Theorymentioning

confidence: 99%

“…Sulfonated calix [n]arenes are consequently versatile water-soluble binding agents able to bind with a significant selectivity a large set of interesting species, whether these latter are molecular or mono-atomic, ionic or neutral, and organic, inorganic or biological [5]. In the case of hexasulfonated calix [6]arenes (C6S) employed in this contribution, let us cite as possible targeted analytes in a non-exhaustive list, UO 2 2+ and some transition metal (Ni 2+ , Zn 2+ , Cu 2+ , Fe 3+ ) [6,7] and lanthanide [8] cations, ferrocene and cobaltocenium derivatives [9][10][11][12], quaternary ammonium cations [13], cationic surfactants [14,15], neutral molecules [16], as well as proteins (such as Bovine Serum Albumine (BSA)), amino-acids, oligo-peptides, drugs, and other small bioactive molecules [17][18] and even iron oxide nanoparticules [19].…”

Section: Introductionmentioning

confidence: 99%

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Correlation between ion-exchange properties and swelling/shrinking processes in hexasulfonated calix[6]arene doped polypyrrole films: ac-electrogravimetry and electrochemical atomic force microscopy investigations

Kim¹,

Gabrielli²,

Pailleret³

et al. 2011

Electrochimica Acta

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. Correlation between ion-exchange properties and swelling/shrinking processes in hexasulfonated calix [6]arene doped polypyrrole films: ac-electrogravimetry and electrochemical atomic force microscopy investigations. Electrochimica Acta, Elsevier, 2011Elsevier, , 56 (10), pp.3516-3525. <10.1016Elsevier, /j.electacta.2010 -00811845> 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 Unexpectedly, within the potential range encompassing this process, K + cations were found to be exchanged for more cathodic potentials whereas H 3 O + are exchanged for more anodic potentials. EC-AFM investigations revealed substantial shrinking and swelling during the oxidation (doping) and reduction (undoping) processes respectively. An obvious correlation can easily be built between these observations: the oxidation of the polymer films provokes an expulsion of the cations, as expected from cation exchanger polymer films, and therefore a decrease of the volume (and thickness) of these films whereas their reduction causes an insertion of cations and an increase of their volume (and thickness). This electromechanical mechanism is amplified by the simultaneous exchange of free water molecules. Suggestions based on these observations, on structural characteristics of polypyrrole films, and on complexation ability of hexasulfonated calix [6]arenes incorporated in the films are discussed to explain i) the change of the identity of the exchanged cations as a function of the potential, ii) the exchange of free water molecules and, iii) the exchange of small amounts of nitrate ions.

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Section: Theorymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Correlation between ion-exchange properties and swelling/shrinking processes in hexasulfonated calix[6]arene doped polypyrrole films: ac-electrogravimetry and electrochemical atomic force microscopy investigations

Kim¹,

Gabrielli²,

Pailleret³

et al. 2011

Electrochimica Acta

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para‐Sulfonated Calixarenes Used as Synthetic Receptors for Complexing Photolabile Cholinergic Ligand

Specht

Ziarelli²,

Bernard³

et al. 2005

Helvetica Chimica Acta

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The water-soluble tetra-, hexa-and octasulfonated calix [4]arenes, calix [6]arenes, and calix [8]arenes 1 -3, respectively, were investigated as potential synthetic receptors for photolabile cholinergic ligand A, a photolytic precursor of choline. Ligand A is a bifunctional molecule carrying a photolabile 2-nitrobenzyl group at one end and a choline moiety at the other end. [4]arene specifically binds the cationic choline moiety, while, at acidic pH, it complexes unselectively both the cationic choline moiety and the aromatic group of A. Our results show that para-sulfonated calixarenes are versatile artificial receptors which bind in various ways to the bifunctional photolabile cholinergic ligand A, depending on their size, geometry, and state of protonation.Introduction. -Molecular recognition is a fundamental biological process that has inspired many chemists to design artificial receptors and enzymes [1]. Among them, the calixarene family is of special importance. Calixarenes are macrocylic molecules consisting of phenolic units connected at the ortho-position by CH 2 bridges. There exist many conformational isomers of calixarenes, and a large number of cavities of different sizes and shapes, which can be involved in molecular recognition processes [2]. Various calixarene-based synthetic receptors have been developed [3], including the watersoluble tetra-, hexa-, and octasulfonated calix [4]arene, calix[6]arene, and calix[8]arenes 1 -3, respectively, which have attracted particular attention because they are able to host the neurotransmitter acetylcholine and related cholinergic ligands, and can, therefore, be used as synthetic cholinergic receptors [4] [5]. The binding of cholinergic ligands to calixarenes is a complex process in which electrostatic forces, hydrophobic effects, and cation-p interactions [6] all play a crucial role. Our interest in developing photolabile cholinergic ligands [7 -11] as possible means to photoregulate the activity of their biological hosts led us to investigate their interactions with calixarenes 1 -3 as model receptors.

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“…[4,5], which play an important role in biochemical processes. Calixarenes can also mimic natural enzyme action [6] and serve as lipophilic containers for the transport of a bioactive guest through cell membranes [7]. One of the most important routes to the synthesis of new bioactive compounds consists of functionalization of the calixarene skeleton with fragments of natural or artificial biologically active compounds [8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Calix[4]arenes bearing α‐amino‐ or α‐hydroxyphosphonic acid fragments at the upper rim

Solovyov

Cherenok

Цымбал

et al. 2001

Heteroatom Chemistry

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Binding of acetylcholine and other quaternary ammonium cations by sulfonated calixarenes. Crystal structure of a [choline-tetrasulfonated calix[4]arene] complex

Cited by 148 publications

References 27 publications

Correlation between ion-exchange properties and swelling/shrinking processes in hexasulfonated calix[6]arene doped polypyrrole films: ac-electrogravimetry and electrochemical atomic force microscopy investigations

Correlation between ion-exchange properties and swelling/shrinking processes in hexasulfonated calix[6]arene doped polypyrrole films: ac-electrogravimetry and electrochemical atomic force microscopy investigations

para‐Sulfonated Calixarenes Used as Synthetic Receptors for Complexing Photolabile Cholinergic Ligand

Calix[4]arenes bearing α‐amino‐ or α‐hydroxyphosphonic acid fragments at the upper rim

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