Synthesis of Bromoundecyl Resorc[4]arenes and Applications of the Cone Stereoisomer as Selector for Liquid Chromatography

Corradi, Silvia; Mazzoccanti, Giulia; Ghirga, Francesca; Quaglio, Deborah; Nevola, Laura; Massera, Chiara; Ugozzoli, Franco; Giannini, Giuseppe; Ciogli, Alessia; D’Acquarica, Ilaria

doi:10.1021/acs.joc.8b00488

Cited by 5 publications

(4 citation statements)

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“…6,9 Importantly, they are chemically stable, structurally preorganized, easy to functionalize, and available in high purity and substantial quantities. 10,11 Recently, we designed and synthesized several resorc [4]arenes as supramolecular artificial linkers for oriented antibody immobilization. 12 In this previous work, we demonstrated that a gold surface plasmon resonance sensor chip surface modification by suitably functionalized resorc [4]arene macrocycles represents a potentially powerful system to improve sensitivity, providing new insight into sensor development.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Most immobilizing approaches − lead to a random orientation of Abs, resulting in lower binding site density and immunoaffinity. In this context, supramolecular chemistry has emerged as a suitable surface modification tool to allow the preorganization of artificial receptors and improve the functional properties of self-assembled monolayers (SAMs). − Among the large pool of supramolecular macrocycles available, resorc[4]arenes, belonging to the family of calixarenes, are characterized by a unique three-dimensional surface that can be functionalized at both the upper and lower rims with several functional groups to tailor their recognition properties toward a specific class of analytes. , Importantly, they are chemically stable, structurally preorganized, easy to functionalize, and available in high purity and substantial quantities. , Recently, we designed and synthesized several resorc[4]arenes as supramolecular artificial linkers for oriented antibody immobilization . In this previous work, we demonstrated that a gold surface plasmon resonance sensor chip surface modification by suitably functionalized resorc[4]arene macrocycles represents a potentially powerful system to improve sensitivity, providing new insight into sensor development .…”

Section: Introductionmentioning

confidence: 99%

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Resorc[4]arene-Modified Gold-Decorated Magnetic Nanoparticles for Immunosensor Development

et al. 2023

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In recent years, several efforts have been made to develop selective, sensitive, fast response, and miniaturized immunosensors with improved performance for the monitoring and screening of analytes in several matrices, significantly expanding the use of this technology in a broad range of applications. However, one of the main technical challenges in developing immunosensors is overcoming the complexity of binding antibodies (Abs) to the sensor surface. Most immobilizing approaches lead to a random orientation of Abs, resulting in lower binding site density and immunoaffinity. In this context, supramolecular chemistry has emerged as a suitable surface modification tool to achieve the preorganization of artificial receptors and to improve the functional properties of self-assembled monolayers. Herein, a supramolecular chemistry/nanotechnology-based platform was conceived to develop sensitive label-free electrochemical immunosensors, by using a resorcarene macrocycle as an artificial linker for the oriented antibody immobilization. To this aim, a water-soluble bifunctional resorc[4]arene architecture (RW) was rationally designed and synthesized to anchor gold-coated magnetic nanoparticles (Au@MNPs) and to maximize the amount of the active immobilized antibody (Ab) in the proper "end-on" orientation. The resulting supramolecular chemistry-modified nanoparticles, RW@Au@MNPs, were deposited onto graphite screen printed electrodes which were then employed to immobilize three different Abs. Furthermore, an immunosensor for atrazine (ATZ) analysis was realized and characterized by the differential pulse voltammetry technique to demonstrate the validity of the developed biosensing platform as a proof of concept for electrochemical immunosensors. The RW-based immunosensor improved Ab ATZ loading on Au@MNPs and sensitivity toward ATZ by almost 1.5 times compared to the random platform. Particularly, the electrochemical characterization of the developed immunosensor displays a linearity range toward ATZ within 0.05−1.5 ng/mL, a limit of detection of 0.011 ng/ml, and good reproducibility and stability. The immunosensor was tested by analyzing spiked fortified water samples with a mean recovery ranging from 95.7 to 108.4%. The overall good analytical performances of this immunodevice suggest its application for the screening and monitoring of ATZ in real matrices. Therefore, the results highlighted the successful application of the resorc[4]arene-based sensor design strategy for developing sensitive electrochemical immunosensors with improved analytical performance and simplifying the Ab immobilization procedure.

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Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Resorc[4]arene-Modified Gold-Decorated Magnetic Nanoparticles for Immunosensor Development

et al. 2023

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“…Within the calixarene family, resorcinol-derived cyclic oligomers, namely resorc[4]arenes, endowed with cavities of molecular dimension, behave as an efficient artificial receptor [ 14 , 25 , 26 ]. The synthetic modularity and different complexation properties of the resorcarene-based macrocycles make them a promising building block for the design and synthesis of more sophisticated supramolecular architectures [ 27 , 28 , 29 , 30 , 31 ]. Efficient solubilizing agents were designed and developed by using several resorc[4]arenes [ 15 , 32 , 33 ].…”

Section: Introductionmentioning

confidence: 99%

Exploring the Assembly of Resorc[4]arenes for the Construction of Supramolecular Nano-Aggregates

Buonsenso

Ghirga

Romeo

et al. 2021

IJMS

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Many biologically active compounds feature low solubility in aqueous media and, thus, poor bioavailability. The formation of the host-guest complex by using calixarene-based macrocycles (i.e., resorcinol-derived cyclic oligomers) with a good solubility profile can improve solubilization of hydrophobic drugs. Herein, we explore the ability of resorc[4]arenes to self-assemble in polar solutions, to form supramolecular aggregates, and to promote water-solubility of an isoflavone endowed with anti-cancer activity, namely Glabrescione B (GlaB). Accordingly, we synthesized several architectures featuring a different pattern of substitution on the upper rim including functional groups able to undergo acid dissociation (i.e., carboxyl and hydroxyl groups). The aggregation phenomenon of the amphiphilic resorc[4]arenes has been investigated in a THF/water solution by UV–visible spectroscopy, at different pH values. Based on their ionization properties, we demonstrated that the supramolecular assembly of resorc[4]arene-based systems can be modulated at given pH values, and thus promoting the solubility of GlaB.

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“…[24,25] The choice of the groups attached at the upper rim plays a pivotal role determining the shape, the rigidity and the complexation properties, whereas the functionalization of the lower rim is functional to surface anchoring. [26][27][28][29][30] Efficient sensor devices were designed and developed by using several resorcarene-based cavitands. [22] However, to date, limited use has been made of resorc [4]arene derivatives as an artificial linker for the site-directed antibody immobilization, giving rise to advanced immunosensors.…”

Section: Introductionmentioning

confidence: 99%

Site‐Directed Antibody Immobilization by Resorc[4]arene‐Based Immunosensors

Quaglio

Mangiardi

Venditti

et al. 2020

Chemistry A European J

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One of the main problems in the development of immunosensors is to overcome the complexity of binding antibody to the sensor surface. Most of immobilizing methods lead to a random orientation of antibodies with a lower binding site density and immunoaffinity. In order to control the orientation of antibody immobilization, several resorc[4]arene derivatives were designed and synthesized. After the spectroscopic characterization of resorc[4]arene self-assembled monolayers (SAMs) onto gold films, the surface coverage and the orientation of insulin antibody (Ab-Ins) were assessed by Surface Plasmon Resonance (SPR) technique and compared with a random immobilization method. Experimental results combined with theoretical studies confirmed the dipole-dipole interaction as an important factor in antibody orientation and demonstrated the importance of the upper rim functionalization of resorcarenes. Accordingly, resorcarene 5 showed a major binding force towards Ab-Ins thanks to the H-bond interactions with the amine protein groups. Based on these findings, the resorcarene-based immunosensor is a powerful system with improved sensitivity providing new insight into sensors development.

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Synthesis of Bromoundecyl Resorc[4]arenes and Applications of the Cone Stereoisomer as Selector for Liquid Chromatography

Cited by 5 publications

References 60 publications

Resorc[4]arene-Modified Gold-Decorated Magnetic Nanoparticles for Immunosensor Development

Resorc[4]arene-Modified Gold-Decorated Magnetic Nanoparticles for Immunosensor Development

Exploring the Assembly of Resorc[4]arenes for the Construction of Supramolecular Nano-Aggregates

Site‐Directed Antibody Immobilization by Resorc[4]arene‐Based Immunosensors

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