Molecular Recognition of Alkylammonium, N-Methylpyridinium Cations and Native L-&amp;#945;-Amino Acids by Water Soluble Penta- and Tetra-Sulfonatocalixarenes

Bonaccorso, Carmela; Gentile, Salvatore; Gulino, Fabio Giuseppe; Sciotto, Domenico

doi:10.2174/157017809790442880

Cited by 5 publications

(5 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Readers interested in the fundamentals of the molecular recognition of amino acids by synthetic binders and hosts, e.g. , calix[ n ]arenes (Cx n ), cucurbit[ n ]urils (CB n ), pillar[ n ]arenes, and cyclodextrins (Figure ), are referred to one of the many literature sources that are available. − Within this section, discussed chemosensors are summarized in Table .…”

Section: Amino Acidsmentioning

confidence: 99%

Molecular Probes, Chemosensors, and Nanosensors for Optical Detection of Biorelevant Molecules and Ions in Aqueous Media and Biofluids

et al. 2022

View full text Add to dashboard Cite

Synthetic molecular probes, chemosensors, and nanosensors used in combination with innovative assay protocols hold great potential for the development of robust, low-cost, and fast-responding sensors that are applicable in biofluids (urine, blood, and saliva). Particularly, the development of sensors for metabolites, neurotransmitters, drugs, and inorganic ions is highly desirable due to a lack of suitable biosensors. In addition, the monitoring and analysis of metabolic and signaling networks in cells and organisms by optical probes and chemosensors is becoming increasingly important in molecular biology and medicine. Thus, new perspectives for personalized diagnostics, theranostics, and biochemical/ medical research will be unlocked when standing limitations of artificial binders and receptors are overcome. In this review, we survey synthetic sensing systems that have promising (future) application potential for the detection of small molecules, cations, and anions in aqueous media and biofluids. Special attention was given to sensing systems that provide a readily measurable optical signal through dynamic covalent chemistry, supramolecular host− guest interactions, or nanoparticles featuring plasmonic effects. This review shall also enable the reader to evaluate the current performance of molecular probes, chemosensors, and nanosensors in terms of sensitivity and selectivity with respect to practical requirement, and thereby inspiring new ideas for the development of further advanced systems.

show abstract

Section: Amino Acidsmentioning

confidence: 99%

Molecular Probes, Chemosensors, and Nanosensors for Optical Detection of Biorelevant Molecules and Ions in Aqueous Media and Biofluids

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Steed, Atwood, Clark, and co-workers reported that the calix[5]arene 73 (Figure a) possessed five to seven negative charges, depending on the pH of the aqueous solution, owing to the presence of five sulfonate groups at its upper rim and the potential ionization of one or two phenolic OHs at its lower rim . Later, Sciotto et al reported the molecular recognition properties of the penta-sodium salt of penta-sulfonate calix[5]arene 73 in water (0.1 M phosphate buffer at pD = 7.3) using a series of organic ammonium guests and amino acids . For example, benzyl trimethylammonium 77 + and the hexa-anionic form of calix[5]arene [ 73 -H] 6– formed a 1:1 inclusion complex featuring an association constant K a = 1.0 × 10 4 M –1 .…”

Section: Covalent Receptors Possessing a Concave Hydrophobic Cavitymentioning

confidence: 99%

“…202 Later, Sciotto et al reported the molecular recognition properties of the penta-sodium salt of penta-sulfonate calix [5]arene 73 in water (0.1 M phosphate buffer at pD = 7.3) using a series of organic ammonium guests 219 and amino acids. 220 For example, benzyl trimethylammonium 77 + and the hexa-anionic form of calix [5]arene [73-H] 6− formed a 1:1 inclusion complex featuring an association constant K a = 1.0 × 10 4 M −1 . NMR and molecular modeling studies (MM3) of the 77 + ⊂[73-H] 6− complex suggested that the guest was included in the electron-rich aromatic cavity of the receptor with a tilted orientation (Figure 35).…”

Section: Covalent Receptors Possessing a Concavementioning

confidence: 99%

Molecular Recognition in Water Using Macrocyclic Synthetic Receptors

2021

View full text Add to dashboard Cite

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.

show abstract

“…Calixarenes and their derivatives are rather easy to synthesise and some show remarkable bioactivity . This is also true for sulfonatocalixarenes, which have already been studied extensively with respect to their inclusion properties in aqueous solution (ammonium ions, amino acids, biological buffer components, neutral species) and in the solid state . Studies carried out by Hof and co‐workers found that p ‐tetrasulfonatocalix[4]arene ( 1 ; Scheme ) was able to discriminate between tri‐, di‐, mono‐ and unmethylated lysine with dissociation constants of 27, 62, 250, and 1923 μ m , respectively, and a Kme 0 /Kme 3 selectivity of 71 (NMR spectroscopy, sodium phosphate buffer; Table ) By using FD assays and glycine buffer, even lower dissociation constants (7.7 μ m for trimethyllysine) and higher selectivity (>130) have been observed .…”

Section: Calixarenesmentioning

confidence: 99%

Synthetic Receptors for the Recognition and Discrimination of Post‐Translationally Methylated Lysines

Gruber

2018

ChemBioChem

View full text Add to dashboard Cite

Post-translational modifications (PTMs) describe the chemical alteration of proteins after their biosynthesis in ribosomes. PTMs play important roles in cell biology, including the regulation of gene expression, cell-cell interactions and the development of different diseases. A prominent class of PTMs is the side-chain methylation of lysine. For the analysis and discrimination of differently methylated lysines, antibodies are widely used, although methylated peptide and protein targets are known to be particularly difficult to differentiate by antibody-based affinity reagents; an additional challenge can be batch-to-batch reproducibility. The application of mass spectrometry techniques for methyllysine discrimination requires a complex sample preparation procedure and is not suited for working in cells. The desire to overcome the above-mentioned challenges has promoted the development of synthetic receptor molecules that recognise and bind methyllysines. Such "artificial antibodies" are of interest for a number of applications, for example, as reagents in biochemical assays, for the isolation and purification of post-translationally methylated proteins and for the tracking of signalling pathways. Moreover, they offer new approaches in diagnostics and therapy. This review delivers an overview of the broad field of methyllysine binding and covers a wide range of synthetic receptors used for the recognition of methylated lysines, including calixarenes, resorcinarenes, pillararenes, disulfide cyclophanes, cucurbiturils and acyclic receptors.

show abstract

Molecular Recognition of Alkylammonium, N-Methylpyridinium Cations and Native L-α-Amino Acids by Water Soluble Penta- and Tetra-Sulfonatocalixarenes

Cited by 5 publications

References 0 publications

Molecular Probes, Chemosensors, and Nanosensors for Optical Detection of Biorelevant Molecules and Ions in Aqueous Media and Biofluids

Molecular Probes, Chemosensors, and Nanosensors for Optical Detection of Biorelevant Molecules and Ions in Aqueous Media and Biofluids

Molecular Recognition in Water Using Macrocyclic Synthetic Receptors

Synthetic Receptors for the Recognition and Discrimination of Post‐Translationally Methylated Lysines

Contact Info

Product

Resources

About