Supramolecular hosts as <i>in vivo</i> sequestration agents for pharmaceuticals and toxins

Deng, Chun‐Lin; Murkli, Steven; Isaacs, Lyle

doi:10.1039/d0cs00454e

Cited by 99 publications

(83 citation statements)

References 53 publications

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“…Cucurbit[n]urils (CB[n]) are macrocycles composed of n glycoluril units, that, owing to their outstanding binding properties, are largely applied for the recognition of several organic molecules and biological analytes ( Figure 6 ) [ 44 , 96 , 97 , 98 , 99 , 100 ]. Thanks to their hydrophobic cavity and highly electronegative carbonyl portals, these macrocyclic containers are particularly suitable to bind positively charged and hydrophobic guests.…”

Section: Receptors For 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: Receptors For Amino Acidsmentioning

confidence: 99%

Selective Recognition of Amino Acids and Peptides by Small Supramolecular Receptors

2020

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“…Supramolecular chemistry, in particular, molecular recognition [1,2] , sensing [3][4][5] and transport [6][7][8][9] have promoted extensive research toward new applications. Out of many synthetic receptors, macrocycles with confined inner spaces distinctly demonstrate the hostguest interaction mechanism: a ring-shaped host possessing a cavity can form an inclusion complex with a suitably sized guest compound.…”

Section: Introductionmentioning

confidence: 99%

“…[47][48][49][50][51][52][53] Herein, we report that cycHC [8] encapsulates small neutral electron-rich organic molecules, namely, five-and six-membered heterocycles containing sulfur and oxygen atoms. This binding was characterized by 1 H NMR titration and isothermal titration calorimetry (ITC) in solution, and the structure of complexes was investigated by single crystal X-ray diffraction (SC-XRD), solid-state NMR (ssNMR), and thermogravimetric analysis (TGA). We compared the sorption properties of the homologs cycHC [6] and cycHC [8] and found that cycHC [8] is a promising sorbent material that can be applied for selective removal of S-containing hydrophobic neutral guests from water, such as 1,3-dithiolane and α-lipoic acid.…”

Section: Introductionmentioning

confidence: 99%

“…Figure 4 1. H NMR and ITC titration for cycHC[8] binding with 1,3-dithiolane (aspectra for NMR titration in CD3OD, bbinding isotherm for NMR titration assuming the 1:1 binding model, K = 7.9 ± 0.2 M −1 , craw thermogram for ITC measurement in 1:1 CH3OH:H2O mixture, dbinding isotherm for ITC measurement using the "one set of sites" model).…”

mentioning

confidence: 99%

“…of each guest compound. The association constant for complexation with 1,3-dithiolane was determined by NMR titration 1. H NMR (400 MHz) spectra in solution were recorded on a Bruker Avance III spectrometer.…”

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confidence: 99%

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Cyclohexanohemicucurbit[8]uril forms inclusion complexes with heterocycles and removes sulfuric guests from water via solid-phase extraction

Shalima¹,

Mishra²,

Kaabel³

et al. 2021

Preprint

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Here we report a study on cyclohexanohemicucurbit[8]uril (cycHC[8]) binding of sulfur-, oxygen- and nitrogen-containing heterocycles in both solid state and solution, which is investigated by single crystal X-ray diffraction, NMR spectroscopy, isothermal titration calorimetry, and thermogravimetry. Potential guests include environmental pollutants, hazardous compounds, and bioactive substances. We found that cycHC[8] encapsulates five- and six-membered sulfur- and oxygen-containing unsubstituted heterocycles and can be used as a selective sorption material for the extraction of sulfur-heterocycles from water. Both cycHC[6] and cycHC[8] can remove a substituted heterocycle, α-lipoic acid, from an aqueous solution via the formation of an external complex. The results show that cycHC[<i>n</i>] is a promising reusable sorbent material with the potential to be employed in molecular recognition and highly specific solid-phase extraction of sulfur-heterocycles.

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A Supramolecular Antidote to Macromolecular Toxins Prepared through Coassembly of Macrocyclic Amphiphiles

Pan

Yue

et al. 2021

Advanced Materials

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Poisoning is a leading cause of admission to medical emergency departments and intensive care units. Supramolecular detoxification, which involves injecting supramolecular receptors that bind with toxins to suppress their biological activity, is an emerging strategy for poisoning treatment; it has few requirements and a broad application scope. However, it is still a formidable challenge to design supramolecular therapeutic materials as an antidote to macromolecular toxins, because the large size, flexible conformation, and presence of multiple and diverse binding sites of biomacromolecules hinder their recognition. Herein, a supramolecular antidote to macromolecular toxins is developed through the coassembly of macrocyclic amphiphiles, relying on heteromultivalent recognition between the coassembled components and toxic macromolecules. The coassembly of amphiphilic cyclodextrin and calixarene strongly and selectively captures melittin, a toxin studied herein; this imparts various therapeutic effects such as inhibiting the interactions of melittin with cell membranes, alleviating melittin cytotoxicity and hemolytic toxicity, reducing the mortality rate of melittin-poisoned mice, and mitigating damage to major organs. The use of the proposed antidote overcomes the limitation of supramolecular detoxification applicability to only small-molecular toxins. The antidote can also detoxify other macromolecular toxins as long as selective and strong binding is achieved because of the coassembling tunability.

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Supramolecular hosts as in vivo sequestration agents for pharmaceuticals and toxins

Abstract: Supramolecular hosts can act as in vivo sequestration agents for pharmaceuticals and toxins.

Cited by 99 publications

References 53 publications

Selective Recognition of Amino Acids and Peptides by Small Supramolecular Receptors

Selective Recognition of Amino Acids and Peptides by Small Supramolecular Receptors

Cyclohexanohemicucurbit[8]uril forms inclusion complexes with heterocycles and removes sulfuric guests from water via solid-phase extraction

A Supramolecular Antidote to Macromolecular Toxins Prepared through Coassembly of Macrocyclic Amphiphiles

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