The chiral interfaces fabricated by <scp>d</scp>/<scp>l</scp>-alanine-pillar[5]arenes for selectively adsorbing ctDNA

Zhang, Jin; Wang, Zhenjun; Lv, Shuxin; Zeng, Xiangfei; Sun, Yao; Li, Haibing; Zhang, Ruiping

doi:10.1039/c8cc09696a

Cited by 34 publications

(23 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We have demonstrated that the chirality of pillar[n]arene derivatives could be manipulated by external stimuli, including temperature, redox, light, and pressure ( Yao et al, 2017 ; Xiao et al, 2020 ; Yao et al, 2021a ; Yao et al, 2021b ). The synthetic approaches for obtaining chiral pillar[5]arenes include introducing chiral or bulky groups on the openings, fusing a side ring onto one subunit, or threading with an axle to block the interconversion between S p and R p conformers ( Ogoshi et al, 2011 ; Chen et al, 2013 ; Strutt et al, 2014b ; Shurpik et al, 2016 ; Li Q. et al, 2019 ; Ma et al, 2019 ; Zhang et al, 2019 ). However, pillar[5]arenes’ planar-chiral S p and R p enantiomers need to be separated by HPLC enantio-resolution of the racemic mixture to study their chiroptical properties.…”

Section: Introductionmentioning

confidence: 99%

Solvent-Driven Chirality Switching of a Pillar[4]arene[1]quinone Having a Chiral Amine-Substituted Quinone Subunit

Liu

Yao

et al. 2021

Front. Chem.

View full text Add to dashboard Cite

Several new chiral pillar[4]arene[1]quinone derivatives were synthesized by reacting pillar[4]arene[1]quinone (EtP4Q1), containing four 1,4-diethoxybenzene units and one benzoquinone unit, with various chiral amines via Michael addition. Due to the direct introduction of chiral substituents on the rim of pillar[n]arene and the close location of the chiral center to the rim of EtP4Q1, the newly prepared compounds showed unique chiroptical properties without complicated chiral resolution processes, and unprecedented high anisotropy factor of up to −0.018 at the charge transfer absorption band was observed. Intriguingly, the benzene sidearm attached pillar[4]arene[1]quinone derivative 1a showed solvent- and complexation-driven chirality inversion. This work provides a promising potential for absolute asymmetric synthesis of pillararene-based derivatives.

show abstract

Section: Introductionmentioning

confidence: 99%

Solvent-Driven Chirality Switching of a Pillar[4]arene[1]quinone Having a Chiral Amine-Substituted Quinone Subunit

Liu

Yao

et al. 2021

Front. Chem.

View full text Add to dashboard Cite

show abstract

“…Amino acids are the main building blocks of many enzymes, proteins and peptides, and play important role in metabolic processes. Consequently, functionalization of macrocyclic compounds by amino acid fragments allows the creation of derivatives with antimicrobial activity, use them as artificial ion channels, for targeted drug delivery, or as cholinesterase inhibitors [ 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 36 , 37 ]. In this regard, the design of synthetic macrocyclic receptors containing amino acid residues is fascinating task for modern organic and supramolecular chemistry.…”

Section: Resultsmentioning

confidence: 99%

“…Introduction of chiral amino acid fragments into the macrocycle’s structure makes it possible to create novel water-soluble receptors based on them. A number of pillararenes containing alanine (Ala) [ 24 , 25 , 26 ], phenylalanine (Phe) [ 27 ], arginine (Arg) [ 28 ], tryptophan (Trp) [ 29 ], glycine (Gly) [ 30 , 31 ] and diglycine (Gly-Gly) [ 32 ] fragments have been reported in the literature. These compounds have been applied in various fields: from the binding of alkali metal cations and dyes to targeted drug delivery and use as ion channels.…”

Section: Introductionmentioning

confidence: 99%

Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes

Nazarova

Shurpik

Padnya

et al. 2020

IJMS

View full text Add to dashboard Cite

Novel water-soluble multifunctional pillar[5]arenes containing amide-ammonium-amino acid moiety were synthesized. The compounds demonstrated a superior ability to bind (1S)-(+)-10-camphorsulfonic acid (S-CSA) and methyl orange dye depending on the nature of the substituent, resulting in the formation one-to-one complexes with both guests. The formation of host-guest complexes was confirmed by ultraviolet (UV), circular dichroism (CD) and 1H NMR spectroscopy. This work demonstrates the first case of using S-CSA as a chiral template for the non-covalent self-assembly of architectures based on pillar[5]arenes. It was shown that pillar[5]arenes with glycine or L-alanine fragments formed aggregates with average hydrodynamic diameters (d) of 165 and 238 nm, respectively. It was established that the addition of S-CSA to the L-alanine-containing derivative led to the formation of micron-sized aggregates with d of 713 nm. This study may advance the design novel stereoselective catalysts and transmembrane amino acid channels.

show abstract

“…The kinetic adsorption process of lysozyme was studied through Electrochemical Impedance Spectroscopy. The adsorption of lysozyme can hinder the electron transfer at the gold interface, and the higher the adsorption amount, the larger the impedance . Therefore, the kinetic adsorption process of lysozyme can be studied through EIS.…”

Section: Figurementioning

confidence: 99%

“…The adsorption of lysozyme can hinder the electron transfer at the gold interface, and the higher the adsorption amount, the larger the impedance. [15] Therefore, the kinetic adsorption process of lysozyme can be studied through EIS. As shown in Figure 4a, the impedance of all interfaces increases with the increase of Figure 3.…”

mentioning

confidence: 99%

Phenethylamine@Pillar[5]arene Biointerface for Highly Enantioselective Adsorption of Protein

Yan

Zhu

et al. 2020

Chemistry An Asian Journal

Self Cite

View full text Add to dashboard Cite

In the life system, the biointerface plays an important role in cell adsorption, platelet adsorption and activation. Therefore, the study of protein adsorption on the biointerface is of great significance for understanding life phenomena and treatment in vitro. In this paper, a chiral biointerface was constructed by the virtue of host‐guest interaction between a water‐soluble pillar[5]arene (WP5) and phenethylamine (PEA) over a gold surface for adsorption of lysozyme proteins. From the experimental results it was identified that the host‐guest biointerface has a high adsorption capacity and strong chiral selectivity. Furthermotre, it was identified that the host‐guest interaction plays the decisive role in the enhancement of chirality of the interface, which was much beneficial for increasing protein adsorption and amplifying the capacity of chiral discrimination. Therefore, this work provides a new idea for the construction of biointerface materials with high protein adsorption capacity and high chiral selectivity through supramolecular interaction, which will have potential applications in the fields of biosensors, biocatalysts, biomaterials.

show abstract

The chiral interfaces fabricated by d/l-alanine-pillar[5]arenes for selectively adsorbing ctDNA

Cited by 34 publications

References 39 publications

Solvent-Driven Chirality Switching of a Pillar[4]arene[1]quinone Having a Chiral Amine-Substituted Quinone Subunit

Solvent-Driven Chirality Switching of a Pillar[4]arene[1]quinone Having a Chiral Amine-Substituted Quinone Subunit

Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes

Phenethylamine@Pillar[5]arene Biointerface for Highly Enantioselective Adsorption of Protein

Contact Info

Product

Resources

About