Review: Cyclodextrin Inclusion Complexes Probed by NMR Techniques

Pessine, Francisco Benedito Teixeira; Calderini, Adriana; Alexandrino, Guilherme L.

doi:10.5772/32029

Cited by 56 publications

(90 citation statements)

References 72 publications

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“…Moreover, T 1 values of the 6CN10 hydrogens signals change between the free and the complexed states, indicating a change of 6CN10 dynamics, which suggest the existence of formation of both complexes (1:2 and 1:1 molar ratios) ( Table 1). 35,36 To obtain further information on the complex formation, 2D ROESY experiments were performed in order to evaluate the mode of complexation and spatial arrangement between 6CN10 and HP-β-CD atoms. Intermolecular cross-peaks were observed between imine and aromatic hydrogens of 6CN10 and HP-β-CD hydrogens (Figure 5), corroborating the 1 H NMR data that showed that the major changes in the chemical shifts happened in the imine and aromatic hydrogens of 6CN10 in complex.…”

Section: D and 2dmentioning

confidence: 99%

Improvement of Solubility and Antifungal Activity of a New Aminothiophene Derivative by Complexation with 2-Hydroxypropyl-β-cyclodextrin

Eleamen¹,

Costa²,

Lima-Neto³

et al. 2016

Journal of the Brazilian Chemical Society

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This study aimed to prepare a complex of 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) and 6CN10, a poorly water soluble 2-aminothiophene derivative with antifungal properties, by freeze-drying technique. The complex was characterized by thermal analysis, infrared/Raman spectroscopy, X-ray diffraction and scanning electron microscopy. In addition, we used the data of the phase solubility study, 1 H, and 2D NMR spectroscopy and molecular modeling in order to investigate the interactions between 6CN10 and HP-β-CD. The apparent solubility of 6CN10 with HP-β-CD increased more than 29 fold. The phase solubility assay in water at 25 ºC showed an A P -type curve, with an apparent stability constant K 1:1 and K 1:2 of 96 and 0.1989 M -1 , respectively. The results of IR, NMR and docking indicate that 6CN10 is able to form complexes with HP-β-CD (1:1 and 1:2 stoichiometric ratios), generating the formation of inclusion and preferably, non-inclusion complexes. The antifungal activity against Cryptococcus neoformans demonstrated the superior performance of the complex (46.66 μg mL -1 ) when compared with the free drug (166.66-333.33 μg mL -1 ). The present study provides useful information for the potential application of complexation with low soluble compounds and about the type of complex formation between 6CN10 and HP-β-CD.

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Section: D and 2dmentioning

confidence: 99%

Improvement of Solubility and Antifungal Activity of a New Aminothiophene Derivative by Complexation with 2-Hydroxypropyl-β-cyclodextrin

Eleamen¹,

Costa²,

Lima-Neto³

et al. 2016

Journal of the Brazilian Chemical Society

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“…[37,38] NMR studies of these and other fluoropolymers are very exciting and useful. [39] The presence of three NMR active nuclei, the high natural abundance of both 1 H and 19 F and the unique NMR properties of 19 F produce NMR spectra with an amazing amount of information. Recently, it has been shown that 19 F detected DOSY experiments could be used to distinguish between the resonances of polymer chain-ends and other branching structures in a series of fluoropolymers.…”

Section: Introductionmentioning

confidence: 99%

“…However, several other nuclei serve as excellent candidates for measuring diffusion via DOSY NMR detection. These include 7 Li, 6 Li (with isotopic enrichment), [27][28][29][30] and 19 F. [31,32] Fluoropolymers are very important because of their unique chemical, mechanical and physical properties. [33,34] In particular, copolymers containing vinylidene fluoride (VDF) [35] or 1-chloro-1,2,2-trifluoroethylene (CTFE), [36] have excellent high temperature stability, resistance to oxidation, resistance to chemical attack by a variety of solvents and corrosive chemicals and a variety of useful commercial properties.…”

Section: Introductionmentioning

confidence: 99%

“…It not only aids in spectral dispersion and resonance assignments, but also provides structural information based on the sizes and shapes of structures. [2][3][4][5][6][7][8][9][10][11] It has been widely used to study the molecular weights of polymers, [12][13][14][15][16][17] and for molecular weight and structure studies of supramolecules, [7,[18][19][20] pharmaceuticals [21] and organometallic complexes. [22,23] In addition, with some care, it is possible to measure the molecular weights and sizes of small molecules.…”

Section: Introductionmentioning

confidence: 99%

“…

ABSTRACT A new pulse sequence for obtaining 19 F detected DOSY (diffusion ordered spectroscopy) spectra of fluorinated molecules is presented and used to study fluoropolymers based on vinylidene fluoride and chlorotrifluoroethylene. The performance of 19

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confidence: 99%

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¹⁹F DOSY diffusion‐NMR spectroscopy of fluoropolymers

Wan

Chen

et al. 2016

Magnetic Reson in Chemistry

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A new pulse sequence for obtaining F detected DOSY (diffusion ordered spectroscopy) spectra of fluorinated molecules is presented and used to study fluoropolymers based on vinylidene fluoride and chlorotrifluoroethylene. The performance of F DOSY NMR experiments (and in general any type of NMR experiment) on fluoropolymers creates some unique complications that very often prevent detection of important signals. Factors that create these complications include: (1) the presence of many scalar couplings among H, F and C; (2) the large magnitudes of many F homonuclear couplings (especially J ); (3) the large F chemical shift range; and (4) the low solubility of these materials (which requires that experiments be performed at high temperatures). A systematic study of the various methods for collecting DOSY NMR data, and the adaptation of these methods to obtain F detected DOSY data, has been performed using a mixture of low molecular weight, fluorinated model compounds. The best pulse sequences and optimal experimental conditions have been determined for obtaining F DOSY spectra. The optimum pulse sequences for acquiring F DOSY NMR data have been determined for various circumstances taking into account the spectral dispersion, number and magnitude of couplings present, and experimental temperature. Pulse sequences and experimental parameters for optimizing these experiments for the study of fluoropolymers have been studied. Copyright © 2016 John Wiley & Sons, Ltd.

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Exploring the Potential of Nanogels: From Drug Carriers to Radiopharmaceutical Agents

Kubeil,

Suzuki,

Casulli

et al. 2023

Adv Healthcare Materials

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Nanogels open up access to a wide range of applications and offer among others hopeful approaches for use in the field of biomedicine. This review provides a brief overview of current developments of nanogels in general, particularly in the fields of drug delivery, therapeutic applications, tissue engineering and sensor systems. Specifically, cyclodextrin (CD)‐based nanogels are important because they have exceptional complexation properties and are highly biocompatible. Nanogels as a whole and CD‐based nanogels in particular can be customized in a wide range of sizes and equipped with a desired surface charge as well as containing additional molecules inside and outside, such as dyes, solubility‐mediating groups or even biological vector molecules for pharmaceutical targeting. Currently, biological investigations are mainly carried out in vitro, but more and more in vivo applications are gaining importance. Modern molecular imaging methods are increasingly being used for the latter. Due to an extremely high sensitivity and the possibility of obtaining quantitative data on pharmacokinetic and pharmacodynamic properties, nuclear methods such as single photon emission computed tomography (SPECT) and positron emission tomography (PET) using radiolabeled compounds are particularly suitable here. The use of radiolabeled nanogels for imaging, but also for therapy, is being discussed.This article is protected by copyright. All rights reserved

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Review: Cyclodextrin Inclusion Complexes Probed by NMR Techniques

Cited by 56 publications

References 72 publications

Improvement of Solubility and Antifungal Activity of a New Aminothiophene Derivative by Complexation with 2-Hydroxypropyl-β-cyclodextrin

Improvement of Solubility and Antifungal Activity of a New Aminothiophene Derivative by Complexation with 2-Hydroxypropyl-β-cyclodextrin

¹⁹F DOSY diffusion‐NMR spectroscopy of fluoropolymers

Exploring the Potential of Nanogels: From Drug Carriers to Radiopharmaceutical Agents

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Review: Cyclodextrin Inclusion Complexes Probed by NMR Techniques

Cited by 56 publications

References 72 publications

Improvement of Solubility and Antifungal Activity of a New Aminothiophene Derivative by Complexation with 2-Hydroxypropyl-β-cyclodextrin

Improvement of Solubility and Antifungal Activity of a New Aminothiophene Derivative by Complexation with 2-Hydroxypropyl-β-cyclodextrin

19F DOSY diffusion‐NMR spectroscopy of fluoropolymers

Exploring the Potential of Nanogels: From Drug Carriers to Radiopharmaceutical Agents

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¹⁹F DOSY diffusion‐NMR spectroscopy of fluoropolymers