The effect of urea moiety in amino acid binding by β-cyclodextrin derivatives: A 1000-fold increase in efficacy comparing to native β-cyclodextrin

Stępniak, Paweł; Lainer, Bruno; Chmurski, Kazimierz; Jurczak, Janusz

doi:10.1016/j.carbpol.2017.02.018

Cited by 9 publications

(14 citation statements)

References 43 publications

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“…In terms of protein detection and analytical studies, aromatic amino acids are important because they give proteins the characteristic 280 nm absorption band and are the only amino acids that present fluorescence, specially tryptophan, with a higher quantum yield than the other aromatic amino acids [34]. Many strategies for the recognition of these amino acids are based on hydrophobic, π-π and ion dipole interactions, making use not only of the aromatic group's characteristic properties but also of the bigger size of these amino acids' side chain [35][36][37][38][39][40][41][42][43][44][45].…”

Section: Aromatic Amino Acidsmentioning

confidence: 99%

Selective Recognition of Amino Acids and Peptides by Small Supramolecular Receptors

2020

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To this day, the recognition and high affinity binding of biomolecules in water by synthetic receptors remains challenging, while the necessity for systems for their sensing, transport and modulation persists. This problematic is prevalent for the recognition of peptides, which not only have key roles in many biochemical pathways, as well as having pharmacological and biotechnological applications, but also frequently serve as models for the study of proteins. Taking inspiration in nature and on the interactions that occur between several receptors and peptide sequences, many researchers have developed and applied a variety of different synthetic receptors, as is the case of macrocyclic compounds, molecular imprinted polymers, organometallic cages, among others, to bind amino acids, small peptides and proteins. In this critical review, we present and discuss selected examples of synthetic receptors for amino acids and peptides, with a greater focus on supramolecular receptors, which show great promise for the selective recognition of these biomolecules in physiological conditions. We decided to focus preferentially on small synthetic receptors (leaving out of this review high molecular weight polymeric systems) for which more detailed and accurate molecular level information regarding the main structural and thermodynamic features of the receptor biomolecule assemblies is available.

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Section: Aromatic Amino Acidsmentioning

confidence: 99%

Selective Recognition of Amino Acids and Peptides by Small Supramolecular Receptors

2020

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“…The solubility of prednisolone increased with increasing concentrations of derivatives [74]. Water-soluble amphiphilic anion receptors were successfully designed based on urea-substituted β -CDs, and the final products were stable [75]. Chitosan was used to functionalize β -CD to form a new product that had improved effect against inflammation-related diseases [76].…”

Section: Six-position Displacementmentioning

confidence: 99%

Selective modifications at the different positions of cyclodextrins: a review ofstrategies

Liu¹,

Zhang²,

Tian³

2020

Turk J Chem

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Cyclodextrins (CDs) are natural, nontoxic, and biodegradable macrocyclic oligosaccharides. As supramolecular hosts, CDs have numerous applications in many aspects. However, nonsubstituted CDs have the disadvantages of solubility, unspecific recognition sites, and weak interactions with guest molecules. Therefore, new CD-based derivatives are successfully designed, synthesized, and widely used in various fields. This contribution outlines the research progress in CD derivatives. In particular, this review emphasizes the synthesis and application of CDs modified through functionalization in definite positions, random substitution, and reconstruction of the skeleton. At the end of this review, a summary and future directions are presented.Recently CDs have a wide range of applications in cancer treatment owing to the particularity of their different ring spaces. CDs could increase the solubility of anticancer flavonoids, such as curcumin and quercetin, which are very poorly soluble in water [41,42]. A novel CD complex of curcumin had superior attributes compared with free curcumin for cellular uptake and for antiproliferative and antiinflammatory activities, preferentially aggregating in the pancreas and possessing strong anticancer activity against pancreatic or tubulin surface cancer cells [41,43]. Similarly, the solubility of quercetin could be improved linearly with the increasing molality of CDs at the same temperature [44]. Selective modifications of CDs at definite positions Monosubstitution of CDsWhen natural CDs are unsuitable for a particular application, chemists begin to modify CDs to allow their derivatives to perform their intended function. To pursue an increasingly perfect structure, the idea of monosubstituted CD derivatives was conceived. However, the direct synthesis of single-isomer CD derivatives is challenging [45]. A single substitution has three possible isomers (Figure 2).

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“…Interestingly, the presence of an isopropyl functionality allows the formation of 'active aggregates' which allow the urea functionality to establish interactions isolated from the bulk solvent. [27] Based on this design, the same group studied a series of compounds and found binding affinities for non-polar amino acids from 2300 M À 1 for alanine to 54 800 M À 1 for tryptophan. Importantly, carboxylates lacking the amino group remained not bound.…”

Section: Cyclodextrinsmentioning

confidence: 99%

Molecular Recognition of Zwitterions with Artificial Receptors

Alfonso

Solà

2020

Chemistry An Asian Journal

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Many biomolecules exist as internal ion pairs or zwitterions within a biologically relevant pH range. Despite their importance, the molecular recognition of this type of systems is specially challenging due to their strong solvation in aqueous media, and their trend to form folded or self‐assembled structures by pairing of charges of different sign. In this Minireview, we will discuss the molecular recognition of zwitterions using non‐natural, synthetic receptors. This contribution does not intend to make a full in‐depth revision of the existing research in the field, but a personal overview with selected representative examples from the recent literature.

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The effect of urea moiety in amino acid binding by β-cyclodextrin derivatives: A 1000-fold increase in efficacy comparing to native β-cyclodextrin

Cited by 9 publications

References 43 publications

Selective Recognition of Amino Acids and Peptides by Small Supramolecular Receptors

Selective Recognition of Amino Acids and Peptides by Small Supramolecular Receptors

Selective modifications at the different positions of cyclodextrins: a review ofstrategies

Molecular Recognition of Zwitterions with Artificial Receptors

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