Facile synthesis of per(6-O-tert-butyldimethylsilyl)-α-, β-, and γ-cyclodextrin as protected intermediates for the functionalization of the secondary face of the macrocycles

Benkovics, Gábor; Cutrone, Giovanna; Béni, Szabolcs; Vargas‐Berenguel, Antonio; Casas‐Solvas, Juan M.

doi:10.1038/s41596-020-00443-8

Cited by 7 publications

(2 citation statements)

References 84 publications

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“…Entrapment elements such as per-6-thio-β-cyclodextrin (β–CD-SH, 95%) and γ-cyclodextrin (γ–CD, 97%) were provided by AraChem (Tilburg, The Netherlands) and Biosynth Carbosynth (Bratislava, Slovakia), respectively. Note that γ–CD was thiolated synthetically [ 25 ], obtaining per-6-thio-γ-cyclodextrin (γ–CD-SH) as the desired reagent in situ.…”

Section: Methodsmentioning

confidence: 99%

Amperometric Inkjet-Printed Thyroxine Sensor Based on Customized Graphene and Tunned Cyclodextrins as the Preconcentration Element

Ortiz-Aguayo,

Paré,

Gabriel

et al. 2024

Nanomaterials

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The determination of thyroid hormones has practical clinical significance for the diagnosis of hyperthyroidism and hypothyroidism diseases. Considering this aspect, a wide range of analytical methods for the detection of analytes, including immunoassay, chemiluminescence, mass spectroscopy and high-performance liquid chromatography, among others, has been developed. This type of analysis provides feasible results. Nevertheless, it requires qualified staff, special facilities and is time-consuming. For this reason, this paper relies on the fabrication of an electrochemical device developed with inkjet printing technology for the free detection of Thyroxine (T4). To manufacture our electrochemical device, several aspects were considered from the use of materials that amplify electrical signals, to finding a supramolecular scaffold that possess affinity towards the target analyte and the need of preconcentrating the analyte on the electrode’s surface. For this task, printed devices were modified with a hybrid nanomaterial consisting of reduced graphene oxide (rGO) tuned with Au nanoparticles (Au–NPs) and an entrapment agent and different thiolated cyclodextrins (x–CD-SH) as carrying agents. Analytes were preconcentrated via supramolecular chemistry due to the formation of an inclusion complex between the cyclodextrin and hormones. Morphological and electrochemical characterization of the final device was carried out to ensure the proper workability of the electrode, achieving excellent response, sensitivity and limit of detection (LOD).

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Section: Methodsmentioning

confidence: 99%

Amperometric Inkjet-Printed Thyroxine Sensor Based on Customized Graphene and Tunned Cyclodextrins as the Preconcentration Element

Ortiz-Aguayo,

Paré,

Gabriel

et al. 2024

Nanomaterials

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“…Native cyclodextrins were first regioselectively silylated on the primary side and then exhaustively acetylated on the secondary side. The synthesis of the per(6- O -tert-butyldimethylsilyl)-α-, β- and γ-cyclodextrin derivatives was achieved according to a previously developed procedure [ 28 ].…”

Section: Methodsmentioning

confidence: 99%

Silylated-Acetylated Cyclodextrins as Chiral Sensors for the Enantiodiscrimination of Fluorinated Anesthetics

et al. 2023

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Silylated-acetylated cyclodextrin (CD) derivatives have recently been investigated, via nuclear magnetic resonance (NMR) spectroscopy, as chiral sensors for substrates that are endowed and devoid of fluorine atoms, and the importance of Si-F interaction in the discrimination phenomena has been assessed. Here, the contributions of both superficial interactions and inclusion processes were further evaluated by extending the records to other chiral fluorinated substrates of interest for pharmaceutical applications. Non-equivalences were measured for both the 1H and 19F resonances in equimolar mixtures with the CDs; the promising results also supported the use of chiral sensors in sub-stoichiometric amounts. Finally, the occurrence of inclusion processes was evaluated by analyzing the intermolecular dipolar interactions by means of ROESY (Rotating-frame Overhauser Enhancement Spectroscopy) experiments. The study confirmed that the γCD derivative is the best chiral solvating agent for the fluorinated substrates investigated, likely due to the higher number of silyl moieties that can be involved in Si-F interactions. The contribution of inclusion processes to the enantiodiscrimination was also confirmed by comparison with the α- and β-analogues. Overall, the CD derivatives proved to be able to discriminate fluorinated substrates even when used in sub-stoichiometric amounts.

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2021–2022

Harvey

2024

Mass Spectrometry Reviews

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The use of matrix‐assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of carbohydrates and glycoconjugates is a well‐established technique and this review is the 12th update of the original article published in 1999 and brings coverage of the literature to the end of 2022. As with previous review, this review also includes a few papers that describe methods appropriate to analysis by MALDI, such as sample preparation, even though the ionization method is not MALDI. The review follows the same format as previous reviews. It is divided into three sections: (1) general aspects such as theory of the MALDI process, matrices, derivatization, MALDI imaging, fragmentation, quantification and the use of computer software for structural identification. (2) Applications to various structural types such as oligo‐ and polysaccharides, glycoproteins, glycolipids, glycosides and biopharmaceuticals, and (3) other general areas such as medicine, industrial processes, natural products and glycan synthesis where MALDI is extensively used. Much of the material relating to applications is presented in tabular form. MALDI is still an ideal technique for carbohydrate analysis, particularly in its ability to produce single ions from each analyte and advancements in the technique and range of applications show little sign of diminishing.

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Facile synthesis of per(6-O-tert-butyldimethylsilyl)-α-, β-, and γ-cyclodextrin as protected intermediates for the functionalization of the secondary face of the macrocycles

Cited by 7 publications

References 84 publications

Amperometric Inkjet-Printed Thyroxine Sensor Based on Customized Graphene and Tunned Cyclodextrins as the Preconcentration Element

Amperometric Inkjet-Printed Thyroxine Sensor Based on Customized Graphene and Tunned Cyclodextrins as the Preconcentration Element

Silylated-Acetylated Cyclodextrins as Chiral Sensors for the Enantiodiscrimination of Fluorinated Anesthetics

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2021–2022

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