Interactions in iodinated contrast media solutions

Giannini, Giovanna; Cuppo, Fábio Luiz Sant'Anna; Fontanive, Luca; D’Amelio, Nicola; Cesàro, Attilio; Maiocchi, Alessandro; Uggeri, Fulvio

doi:10.1007/s10973-010-1090-4

Cited by 4 publications

(7 citation statements)

References 21 publications

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“…However, if the transformation rate is slow enough, the syn and anti forms in solution must be considered as distinct thermodynamic species, therefore, the saturation molality may depend on the solution population of the conformation (syn or anti) of the corresponding crystalline solid. An additional anomaly arises from the sign of the heat of dilution, 32 which shows a slightly hydrophobic character of iopamidol with consequences on its temperature dependence properties in water.…”

Section: Some Thermodynamic Considerationsmentioning

confidence: 99%

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Myelography Iodinated Contrast Media. 2. Conformational Versatility of Iopamidol in the Solid State

et al. 2017

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The phenomenon of polymorphism is of great relevance in pharmaceutics, since different polymorphs have different physicochemical properties, e.g., solubility, hence, bioavailability. Coupling diffractometric and spectroscopic experiments with thermodynamic analysis and computational work opens to a methodological approach which provides information on both structure and dynamics in the solid as well as in solution. The present work reports on the conformational changes in crystalline iopamidol, which is characterized by atropisomerism, a phenomenon that influences both the solution properties and the distinct crystal phases. The conformation of iopamidol is discussed for three different crystal phases. In the anhydrous and monohydrate crystal forms, iopamidol molecules display a syn conformation of the long branches stemming out from the triiodobenzene ring, while in the pentahydrate phase the anti conformation is found. IR and Raman spectroscopic studies carried out on the three crystal forms, jointly with quantum chemical computations, revealed that the markedly different spectral features can be specifically attributed to the different molecular conformations. Our results on the conformational versatility of iopamidol in different crystalline phases, linking structural and spectroscopic evidence for the solution state and the solid forms, provide a definite protocol for grasping the signals that can be taken as conformational markers. This is the first step for understanding the crystallization mechanism occurring in supersaturated solution of iopamidol molecules.

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Section: Some Thermodynamic Considerationsmentioning

confidence: 99%

“… a All data refer to 25 °C. b Reference . c Data fitting from literature data (ref ). d Reference . e The properties of the amorphous are approximated by the dependence of the glass transition temperature with composition or not available. …”

Section: Some Thermodynamic Considerationsmentioning

confidence: 99%

Myelography Iodinated Contrast Media. 2. Conformational Versatility of Iopamidol in the Solid State

et al. 2017

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“…In particular, a preliminary report on the differences in the thermodynamic properties of the compounds iopamidol, iomeprol, and iopromide in aqueous solution has already been reported. 11 ■ RESULTS AND DISCUSSION 1. NMR Assignment of Iomeprol, Iopamidol, and Iopromide.…”

Section: Molecular Pharmaceuticsmentioning

confidence: 99%

“…Thus, the investigation of the conformational energetics of transitions primarily refers not only to the rotations φ1, φ3, and φ5 but also to the conformational freedom of the hydrophilic side chains. As a corollary, because the hydrophilic character of iomeprol appears to be different from that of iopamidol and iopromide, 11 the hydration properties of the three molecules will be treated in more detail elsewhere. 7 Hindered Conformation at the Ring-Linked Bonds.…”

Section: Molecular Pharmaceuticsmentioning

confidence: 99%

“…Literature data on iopamidol and analogues in solution at room temperature have shown that the syn and anti conformers are populated in similar amounts and that their splitting into endo/exo populations exists only when the anilide moiety is a tertiary amide, but no reference was made in this particular work to SYN/ANTI forms. Furthermore, other studies on the physicochemical properties of NICMs do not deal with molecular conformation in aqueous solution, but rather refer to the question of the association equilibria as a function of concentration, studied by osmolality, calorimetry, and densitometry, ,− in order to correlate the free energy, enthalpy, and volume properties of NICM solutions. In particular, a preliminary report on the differences in the thermodynamic properties of the compounds iopamidol, iomeprol, and iopromide in aqueous solution has already been reported …”

Section: Structure and Hindered Rotations In Nicmsmentioning

confidence: 99%

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Myelography Iodinated Contrast Media. I. Unraveling the Atropisomerism Properties in Solution

Fontanive

D’Amelio²,

Cesàro

et al. 2015

Mol. Pharmaceutics

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The present work reports a thorough conformational analysis of iodinated contrast media: iomeprol, iopamidol (the world's most utilized contrast agent), and iopromide. Its main aim is the understanding of the complex structural features of these atropisomeric molecules, characterized by the presence of many conformers with hindered rotations, and of the role of atropisomerism in the physicochemical properties of their aqueous solutions. The problem was tackled by using an extensive analysis of (13)C NMR data on the solutions of whole molecules and of simple precursors in addition to FT-IR investigation and molecular simulations. This analysis demonstrated that out of the many possible atropisomers, only a few are significantly populated, and their relative population is provided. The conformational analysis also indicated that the presence of a sterically hindered amidic bond, allowing a significant population of cis forms (E in iopromide and exo in iomeprol), may be the basis for an increased thermodynamic solubility of concentrated solutions of iomeprol.

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Enhancing the Charge Transport in Solution‐Processed Perylene Di‐imide Transistors via Thermal Annealing of Metastable Disordered Films

Ferlauto

Liscio

Orgiu

et al. 2014

Adv Funct Materials

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The application of replica molding has proven to be a valuable tool in the analysis of different forensic evidences in particular for its ability to extract the toolmarks from complex sample surfaces. A well known problem in the analysis of ballistic evidences is the accurate characterization of the lateral striae of real bullets seized on crime scenes after shots, due primarily to impact deformations and to unpredictable issues related to laboratory illumination setup. To overcome these problems a possible way is to confine over a flat surface all the features still preserving their three dimensionality. This can be achieved by a novel application of replica molding performed onto the relevant lateral portion of the bullet surface.\ud \ud A quasi-two-dimensional negative copy of the original tridimensional indented surface has been thus fabricated. It combines the real tridimensional topography of class characteristics (land and groove impressions) and of individual caracteristics (striae) impressed by rifled barrels on projectiles, moreover with the possibility of quantitative characterization of these features in a planar configuration, that will allow one-shot comparison of the “whole striae landscape” without the typical artifacts arising from the bullet shape and the illumination issue.\ud \ud A detailed analysis has been carried on at the morphological level by standard optical and scanning electron microscopy, while the 3D topography has been characterized by white light optical profilometry.\ud \ud A quantitative characterization of toolmarks of bullets derived from ammunitions shot by guns of large diffusion, as the Beretta 98 FS cal. 9 × 21 mm, has been performed and will be presented ranging between the whole landscape and the sub-μm resolution. To investigate the real potentiality of this technique, the experiment has been extended to highly impact-deformed projectiles

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Interactions in iodinated contrast media solutions

Cited by 4 publications

References 21 publications

Myelography Iodinated Contrast Media. 2. Conformational Versatility of Iopamidol in the Solid State

Myelography Iodinated Contrast Media. 2. Conformational Versatility of Iopamidol in the Solid State

Myelography Iodinated Contrast Media. I. Unraveling the Atropisomerism Properties in Solution

Enhancing the Charge Transport in Solution‐Processed Perylene Di‐imide Transistors via Thermal Annealing of Metastable Disordered Films

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