Molecular recognition of ω-amino acids by thiazolobenzocrown receptors: a GABA-selective ionophore

Yi, Young Rae; Kim, Ki-Soo; Helal, Aasif; Kim, Hong-Seok

doi:10.1080/10610278.2012.726731

Cited by 6 publications

(4 citation statements)

References 48 publications

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“…In separate work, thiazolobenzocrown receptors were also reported to act as GABA-selective ionophores. 213 De Mendoza and co-workers described the preparation and binding properties of a ditopic receptor 134 bearing a monoaza [18]crown-6 for ammonium cation recognition and a guanidine group for carboxylate anion complexation. 214 In this system, an aromatic planar surface (the naphthalene ring) was included in the structural design so as to enhance the affinity for aromatic amino acids via π−π donor−acceptor interactions.…”

Section: Zwitterionsmentioning

confidence: 99%

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Macrocycles as Ion Pair Receptors

et al. 2019

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Cation and anion recognition have both played central roles in the development of supramolecular chemistry. Much of the associated research has focused on the development of receptors for individual cations or anions, as well as their applications in different areas. Rarely is complexation of the counterions considered. In contrast, ion pair recognition chemistry, emerging from cation and anion coordination chemistry, is a specific research field where co-complexation of both anions and cations, so-called ion pairs, is the center of focus. Systems used for the purpose, known as ion pair receptors, are typically di-or polytopic hosts that contain recognition sites for both cations and anions and which permit the concurrent binding of multiple ions. The field of ion pair recognition has blossomed during the past decades. Several smaller reviews on the topic were published roughly 5 years ago. They provided a summary of synthetic progress and detailed the various limiting ion recognition modes displayed by both acyclic and macrocyclic ion pair receptors known at the time. The present review is designed to provide a comprehensive and up-to-date overview of the chemistry of macrocycle-based ion pair receptors. We specifically focus on the relationship between structure and ion pair recognition, as well as applications of ion pair receptors in sensor development, cation and anion extraction, ion transport, and logic gate construction. CONTENTS 3.4.

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Section: Zwitterionsmentioning

confidence: 99%

“…Compared with the constituent cationic ammonium substrates, the association constants for zwitterionic amino acids displayed by 133 were increased by a factor of 2.5. In separate work, thiazolobenzocrown receptors were also reported to act as GABA-selective ionophores …”

Section: Recognition With Macrocyclic Ion Pair Receptorsmentioning

confidence: 99%

Macrocycles as Ion Pair Receptors

et al. 2019

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“…Given the fact that, pregabalin as an amino acid derivative with amino, carboxylic groups and hydrophobic moiety, must to be taken into consideration to be recognized, attention will be turned toward a multitopic receptor approach [33,34].…”

Section: Performance Characteristics Of Pregabalin Selective Sensorsmentioning

confidence: 99%

Potentiometric sensing platform for selective determination of Pregabalin in pharmaceutical formulations

El-Naby¹

2019

Open J Anal Bioanal Chem

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Pregabalin is a structural analogue of, but functionally unrelated to, the naturally occurring neurotransmitter -aminobutyric acid (GABA) with potent analgesic, anticonvulsant and anxiolytic activity.The abuse potential of pregabalin is a well-documented with high risk of addiction that may be fatal with overdoses particularly, among opiate addicts and polydrug use dependency syndrome, consequently, it is very pertinent to determine pregabalin in a sensitive and selective manner. Herein, for the fi rst time the use of β-cyclodextrin:phosphomolybdic acid organic-inorganic hybrid material as a neutral ionophore in polymeric membrane based selective sensors for the determination of pregabalin in its pharmaceutical formulations has been reported. The fabricated sensors yielded an excellent performance, with a linear range from 1.0×10 6 to 1.0×10 1 M pregabalin, a response slope closer to the ideal Nernstian value; 59.6 mV per decade as well as a detection limit was 6.0×10 7 M and very short response time of about 5 s for high concentrations. The most interesting feature of the sensors is their remarkably selective recognition for pregabalin compared with opioids and this is an important issue that is suited to practical applications. The sensors were effectively used for the determination of pregabalin in pharmaceutical formulations with a recovery of 100.97%±0.17. On comparison with β-cyclodextrin, the proposed sensors exhibited the best performance characteristics.

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“…Since the pioneering research on the application of chiral recognition reported by Cram and coworkers, great number of chiral macrocyclic and complex structured ligands have been synthesized and studied for enantiomeric recognition of racemic compounds (Nakashima et al, 2000;Lu et al, 2010;Lee et al, 2010;Deniz et al, 2011;Park et al, 2012;Sipos et al, 2012;Bako et al, 2012;Howard et al, 2013;Yi et al, 2013;Tsioupi et al, 2013;Paik et al, 2013;Guo et al, 2013;Liu et al, 2014;Şeker et al, 2014) However, in recent years non-cyclic ligands have begun to be used in enantiomeric recognition studies (Peri et al, 1998;Liu et al, 2001;Wang et al, 2007;Ballistreri et al, 2010;Aral et al, 2013;Kormos et al, 2013;Ulatowski and Jurczak, 2014;Pal et al, 2015;Forte et al, 2015;Pal et al, 2016). Still there are limited papers have been reported on the using non-cyclic ligands as chiral receptor for enantiomeric recognition of the racemic compounds.…”

Section: Introductionmentioning

confidence: 99%