Selective recognition of oxalate in water: effect of pH on binding strength and sensing mechanisms

Mittapalli, Ramana R.; Namashivaya, Siva S. R.; Oshchepkov, Aleksandr S.; Shumilova, Tatiana A.; Rüffer, Tobias; Lang, Heinrich; Kataev, Evgeny A.

doi:10.1039/c7cc06955c

Cited by 17 publications

(11 citation statements)

References 42 publications

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“…On the other hand, structurally simple cyclophanes bearing para -benzene derivatives at the “roof” and “floor” were designed. − As discussed above for cyclophane [ 18 +4H] 4+ , ammonium groups were incorporated to deliver water solubility. The cationic nature of these simple cyclophanes was applied in the binding of organic and inorganic anions such as carboxylate and sulfate, respectively.…”

Section: Cyclic and Oligocyclic Covalent Receptors Featuring A Hydrop...mentioning

confidence: 99%

Molecular Recognition in Water Using Macrocyclic Synthetic Receptors

2021

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Molecular recognition in water using macrocyclic synthetic receptors constitutes a vibrant and timely research area of supramolecular chemistry. Pioneering examples on the topic date back to the 1980s. The investigated model systems and the results derived from them are key for furthering our understanding of the remarkable properties exhibited by proteins: high binding affinity, superior binding selectivity, and extreme catalytic performance. Dissecting the different effects contributing to the proteins' properties is severely limited owing to its complex nature. Molecular recognition in water is also involved in other appreciated areas such as self-assembly, drug discovery, and supramolecular catalysis. The development of all these research areas entails a deep understanding of the molecular recognition events occurring in aqueous media. In this review, we cover the past three decades of molecular recognition studies of neutral and charged, polar and nonpolar organic substrates and ions using selected artificial receptors soluble in water. We briefly discuss the intermolecular forces involved in the reversible binding of the substrates, as well as the hydrophobic and Hofmeister effects operating in aqueous solution. We examine, from an interdisciplinary perspective, the design and development of effective water-soluble synthetic receptors based on cyclic, oligo-cyclic, and concave-shaped architectures. We also include selected examples of self-assembled watersoluble synthetic receptors. The catalytic performance of some of the presented receptors is also described. The latter process also deals with molecular recognition and energetic stabilization, but instead of binding ground-state species, the targets become elusive counterparts: transition states and other high-energy intermediates.

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Section: Cyclic and Oligocyclic Covalent Receptors Featuring A Hydrop...mentioning

confidence: 99%

Molecular Recognition in Water Using Macrocyclic Synthetic Receptors

2021

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“…Since our receptor is highly charged, these interactions can be relatively strong. For instance, such a 1 : 2 binding mode we have observed recently in the solid structure of an oxalate complex …”

Section: Methodsmentioning

confidence: 71%

“…The fluorescence enhancement observed with oxalate is in a good agreement with those results observed for the receptors reported by us previously. [20] This fact indicates that coordination of oxalate induces the protonation of the receptor, i. e. it increases the population of 4-fold protonation state.…”

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confidence: 99%

“…For instance, such a 1 : 2 binding mode we have observed recently in the solid structure of an oxalate complex. [20] Given the fact that oxalate induces the strongest emission enhancement, we tested other dicarboxylates. Interestingly, fumarate demonstrated a slightly higher binding constant as compared to that of oxalate, but similar 1.5-fold fluorescence enhancement ( Figure S8).…”

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confidence: 99%

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Anthracene‐Based Amido−Amine Cage Receptor for Anion Recognition under Neutral Aqueous Conditions

et al. 2019

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A new amido−amine cage receptor, which combines 1,8‐anthracene diacarboxamide subunit and a polyammonium azamacrocycle, is reported. Bearing both the hydrogen bond donor and the acceptor binding sites, the receptor is able to bind phosphate selectively under neutral (pH 7.2) aqueous conditions. The recognition events for phosphate and dicarboxylates are accomplished by a fluorescence enhancement in the anthracene emission. As revealed by experimental and theoretical studies, phosphate and oxalate show different recognition modes. Phosphate demonstrates hydrogen bond acceptor properties, while the coordination of oxalate favours the protonation of the receptor.

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“…[27][28] Using a supramolecular approach, there has been an immense interest in developing efficient chemical sensors for oxalate by colorimetric and fluorescence methods. [29][30][31][32][33][34][35][36][37][38][39][40][41] Previous studies demonstrated that the complexes of certain metal ions including zinc, [32][33] copper, [34][35][36][37][38][39] nickel, [40][41] and calcium [42] can be used as suitable chemosensors for detecting an oxalate anion in solution.…”

Section: Introductionmentioning

confidence: 99%

Molecular Recognition of Biologically Relevant Anions with an Expanded Dinuclear Copper(II) Complex: An Efficient Sensor for Oxalate Anion in Aqueous Solution

et al. 2021

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An expanded dinuclear copper(II) complex (1) derived from a biphenyl‐based hexaazamacrocyle (L) was synthesized and characterized by single crystal X‐ray analysis, exhibiting a boat‐shaped cavity with an elongated CuII⋅⋅⋅CuII distance of 11.01 Å. The dinuclear copper(II) complex was investigated for a verity of biologically relevant anions including carboxylates (oxalate, citrate, tartrate, glutamate, adipate, acetate and benzoate), oxoanions (phosphate, sulphate, perchlorate and nitrate), and halides (fluoride, chloride, bromide and iodide) by competitive fluorescence titrations via indicator displacement assay (IDA) using an external dye (Eosin Y) in water‐methanol solution at neutral pH. The receptor was shown to exhibit strong affinity for oxalate, providing the binding trend: oxalate (log K=6.07)>citrate (log K=5.74)>phosphate (log K=5.02)>tartrate (log K=4.78)>glutamate (log K=4.42)>adipate (log K=4.31)>acetate (log K=4.14)>benzoate (log K=4.01). No interaction was observed for other anions including sulphate, perchlorate, nitrate, fluoride, chloride, bromide and iodide under the identical conditions.

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Selective recognition of oxalate in water: effect of pH on binding strength and sensing mechanisms

Cited by 17 publications

References 42 publications

Molecular Recognition in Water Using Macrocyclic Synthetic Receptors

Molecular Recognition in Water Using Macrocyclic Synthetic Receptors

Anthracene‐Based Amido−Amine Cage Receptor for Anion Recognition under Neutral Aqueous Conditions

Molecular Recognition of Biologically Relevant Anions with an Expanded Dinuclear Copper(II) Complex: An Efficient Sensor for Oxalate Anion in Aqueous Solution

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