Synthesis and Characterization of Ligands and their Gadolinium(III) Complexes

Kotek, Jan; Kubíček, Vojtěch; Hermann, Petr; Lukeš, Ivan

doi:10.1002/9781118503652.ch3

The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging 2013

DOI: 10.1002/9781118503652.ch3

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Synthesis and Characterization of Ligands and their Gadolinium(III) Complexes

Jan Kotek¹,

Vojtěch Kubíček²,

Petr Hermann³

et al.

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Cited by 3 publications

(1 citation statement)

References 454 publications

(506 reference statements)

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“…These compounds shorten the relaxation times of water protons, allowing abnormal tissue to appear brighter than the surrounding tissue. The most common contrast agents comprise gadolinium cations chelated by linear or macrocyclic ligands and are employed in approximately 25–30% of all MRI procedures . Gadolinium, however, is not an innocuous element as suggested by several disorders associated with its use. , For instance, the administration of gadolinium-based contrast agents (GBCA) to patients with renal dysfunction has been strongly associated with consequential nephrogenic systemic fibrosis, , and the accumulation of gadolinium has been observed in the brains of healthy individuals who underwent MRI scan with GBCAs. − As a result, the U.S. Food and Drug Administration (FDA) issued a public warning against retention of GBCAs in the body, with special attention to contrast agents based on linear ligands .…”

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confidence: 99%

Rapid Detection of Gadolinium-Based Contrast Agents in Urine with a Chelated Europium Luminescent Probe

Pallares

Tewari

et al. 2020

ACS Sens.

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Gadolinium-based contrast agents are widely used in magnetic resonance imaging procedures to enhance image contrast. Despite their ubiquitous use in clinical settings, gadolinium is not an innocuous element, as suggested by several disorders associated with its use. Therefore, novel analytical technologies capable of tracking contrast agent excretion through urine are necessary for optimizing patient safety after imaging procedures. Here, we describe an assay to detect and quantify contrast agents in urine based on the luminescence quenching of a metal chelate probe, Eu3+–3,4,3-LI(1,2-HOPO), which only requires 10 min incubation before measurement. Gadolinium-based contrast agents prevent the formation of the Eu3+–3,4,3-LI(1,2-HOPO) complex, subsequently decreasing the luminescence of the assay solution. Three commercial contrast agents, Magnevist, Multihance, and Omniscan, were used to demonstrate the analytical concept in synthetic human urine, and subsequent quantification of mouse urine samples. To the best of our knowledge, this is the first assay capable of detecting and quantifying gadolinium-based contrast agents in urine without sample preparation or digestion.

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mentioning

confidence: 99%

Rapid Detection of Gadolinium-Based Contrast Agents in Urine with a Chelated Europium Luminescent Probe

Pallares

Tewari

et al. 2020

ACS Sens.

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The Reactivity of Multidentate Schiff Base Ligands Derived from Bi‐ and Terphenyl Polyamines towards M(II) (M=Ni, Cu, Zn, Cd) and M(III) (M=Co, Y, Lu)

et al. 2021

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Multidentate Schiff base ligands derived from a selection of biphenyl-and terphenyl polyamines were synthesized, and their reactivity towards divalent (Ni, Cu, Zn, Cd) and trivalent (Co, Y, Lu) metals was studied by single-crystal X-ray diffraction analysis, NMR spectroscopy, and UV/Vis spectroscopy for the Cu(II) complexes. Large variations in the resulting complexes were observed based on the relative position of the amine substituents in the parent triamines, as well as the electronic properties of the Schiff base ligand itself. Most notably, Schiff base ligands derived from a m-terphenyl-2,2',2''-triamine were found to coordinate in a tetradentate, pentadentate or hexadentate fashion, depending on the size and the valency of the corresponding metal center.

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MRI Gadolinium‐Based Contrast Media: Meeting Radiological, Clinical, and Environmental Needs

Bendszus,

Laghi,

Munuera

et al. 2024

Magnetic Resonance Imaging

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Gadolinium‐based contrast agents (GBCAs) are routinely used in magnetic resonance imaging (MRI). They are essential for choosing the most appropriate medical or surgical strategy for patients with serious pathologies, particularly in oncologic, inflammatory, and cardiovascular diseases. However, GBCAs have been associated with an increased risk of nephrogenic systemic fibrosis in patients with renal failure, as well as the possibility of deposition in the brain, bones, and other organs, even in patients with normal renal function. Research is underway to reduce the quantity of gadolinium injected, without compromising image quality and diagnosis. The next generation of GBCAs will enable a reduction in the gadolinium dose administered. Gadopiclenol is the first of this new generation of GBCAs, with high relaxivity, thus having the potential to reduce the gadolinium dose while maintaining good in vivo stability due to its macrocyclic structure. High‐stability and high‐relaxivity GBCAs will be one of the solutions for reducing the dose of gadolinium to be administered in clinical practice, while the development of new technologies, including optimization of MRI acquisitions, new contrast mechanisms, and artificial intelligence may help reduce the need for GBCAs. Future solutions may involve a combination of next‐generation GBCAs and image‐processing techniques to optimize diagnosis and treatment planning while minimizing exposure to gadolinium.Level of Evidence5Technical EfficacyStage 3

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Synthesis and Characterization of Ligands and their Gadolinium(III) Complexes

Cited by 3 publications

References 454 publications

Rapid Detection of Gadolinium-Based Contrast Agents in Urine with a Chelated Europium Luminescent Probe

Rapid Detection of Gadolinium-Based Contrast Agents in Urine with a Chelated Europium Luminescent Probe

The Reactivity of Multidentate Schiff Base Ligands Derived from Bi‐ and Terphenyl Polyamines towards M(II) (M=Ni, Cu, Zn, Cd) and M(III) (M=Co, Y, Lu)

MRI Gadolinium‐Based Contrast Media: Meeting Radiological, Clinical, and Environmental Needs

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