Synthesis and Biocompatibility Studies of New Iminodiacetic Acid Derivatives

Markowicz-Piasecka, Magdalena; Dębski, Piotr; Mikiciuk-Olasik, Elżbieta; Sikora, Joanna

doi:10.3390/molecules22122265

Cited by 5 publications

(3 citation statements)

References 38 publications

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“…However, only 99m Tc-IDA (Figure 1A) using SPE-CT is currently the imaging-based hepatocellular function test used to diagnose various hepatobiliary pathologies, including primary biliary cirrhosis, acute hepatitis, and jaundice, among others [47]. For these purposes, many IDA derivatives have been synthesized [48].…”

Section: Probes Based On 99m Tcmentioning

confidence: 99%

Monitoring the hepatobiliary function using image techniques and labeled cholephilic compounds

et al. 2023

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Evaluation of the hepatobiliary function is critical for the clinicians, not only for the diagnosis of a large variety of liver diseases but also in the follow-up and management of some patients, for instance, those with different degrees of cholestasis suffering from a drug-induced liver injury (DILI) or scheduled for liver resection. Currently, the determination of global liver function mainly relies on laboratory tests, clinical scores, and data from images obtained with ultrasonography, computed tomography (CT), or magnetic resonance. Nuclear medicine scanning, displaying either planar or three-dimensional spatial distribution of liver function, is enhanced when using hepatotropic tracers based on classical radioisotopes such as technetium-99m (99mTc) and with higher resolution using metabolized probes such as those based on monosaccharide derivatives labeled with 18F. Other cholephilic compounds, and hence selectively secreted into bile, have been proposed to visualize the correct function of the liver parenchyma and the associated secretory machinery. This review aims to summarize the state-of-the-art regarding the techniques and chemical probes available to monitor liver and gallbladder function, in some cases based on imaging techniques reflecting the dynamic of labeled cholephilic compounds.

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Section: Probes Based On 99m Tcmentioning

confidence: 99%

Monitoring the hepatobiliary function using image techniques and labeled cholephilic compounds

et al. 2023

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“…Furthermore, the other supporting features of ADA, i.e., the presence of multiple hard donor sites, deprotonation under physiological conditions, biologically safe, and high bioavailability, point toward its great potential for application in humans as a Th-decorporating agent. N-substituted iminodiacetic acid ligands are reported to be biologically safe and proposed to have medical application as potential metallo-β-lactamase inhibitors. , …”

Section: Introductionmentioning

confidence: 99%

“…N-substituted iminodiacetic acid ligands are reported to be biologically safe and proposed to have medical application as potential metallo-β-lactamase inhibitors. 47,48 The development of an efficient decorporating agent is a subject of chemical and biological interphase. In order to understand the biological effects of ADA with respect to Th decorporation, it is important to have a priori knowledge of its protonation as well as complexation behavior with Th.…”

Section: Introductionmentioning

confidence: 99%

Combined Thermodynamic, Theoretical, and Biological Study for Investigating N-(2-Acetamido)iminodiacetic Acid as a Potential Thorium Decorporation Agent

Sharma,

Ali,

Kumar

et al. 2023

Inorg. Chem.

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The most effective approach to mitigate the toxic effects of internal exposure of radiometals to humans is metal–ligand (ML) chelation therapy. Thorium (Th)-induced carcinogenesis as well as other health hazards to humans as a result of chronic internal exposure necessitates the development of efficient Th-decorporating agents. In this regard, chemical and biological studies were carried out to evaluate N-(2-Acetamido)iminodiacetic acid (ADA), a comparatively cost-effective, readily available, and biologically safe complexing agent for Th decorporation. In the present work, detailed thermodynamic studies for complexation of ADA with Th(IV) have been carried out to understand Th-ADA interaction, using potentiometry, calorimetry, electrospray ionization mass spectrometry, and theoretical studies, followed by its biological assessment for Th decorporation. Thermodynamic studies revealed the formation of strong Th-ADA complexes, which are enthalpically as well as entropically favored. Interestingly, density functional theory calculations, to obtain a thermodynamically favored mode of coordination, showed the uncommon trend of lower denticity of ADA in ML than in ML2, which has been explained on the basis of stabilization of ML by hydrogen bonding. The same was also reflected in the unusual trend of enthalpy for Th-ADA complexes. Biological experiments using human erythrocytes, whole human blood, and lung cells showed good cytocompatibility and ability of ADA to significantly prevent Th-induced hemolysis. Th removal of ADA from erythrocytes, human blood, and normal lung cells was found to be comparable with that of diethylenetriamine pentaacetate (DTPA), an FDA approved decorporating agent. The present study contributed significant data about Th complexation chemistry of ADA and its Th decorporation efficacy from human erythrocytes, blood, and lung cells.

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Biocompatibility Studies of Gadolinium Complexes with Iminodiacetic Acid Derivatives

Markowicz-Piasecka

Skupień

Mikiciuk-Olasik

et al. 2018

Biol Trace Elem Res

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Apart from using as radiopharmaceuticals, iminodiacetic acid derivatives, after complexation with gadolinium, have been also tested as MRI CAs (magnetic resonance imaging contrast agents) since they show high affinity to hepatocytes and therefore provide high-resolution MRI of the liver. The purpose of this study was to evaluate the biocompatibility of four gadolinium complexes with iminodiacetic acid (IDA) derivatives differing in substituent in aromatic ring by estimating their influence on plasma hemostasis, integrity of erythrocyte membrane, and toxicity towards human umbilical vein endothelial cells (HUVECs). The influence of gadolinium-based CAs on plasma hemostasis was evaluated by measuring PT (prothrombin time), APTT (activated partial tromboplastin time), and TT (thrombin time). The effects of tested compounds on RBCs (Red Blood Cells) were assessed using hemolysis assay and microscopy studies. The influence of gadolinium complexes on the barrier properties of HUVECs was assessed by means of real-time method based on the measurements of the impedance changes of the cells. Gadolinium complexes did not affect significantly PT and TT. APTT measurements revealed significant prolongation in the presence of all tested gadolinium complexes at the concentration higher than 0.5 μmol/mL. Hemolysis assay showed that compounds with alkyl substituents in benzene ring without halogen atom (1-3) do not exert unfavorable effect on the integrity of erythrocyte membrane over the entire concentration range. All gadolinium complexes at 1.0 μmol/mL contribute to the decrease in HUVEC viability and integrity. To conclude, the study describes biocompatibility studies of gadolinium-based CAs, provides additional insight into their potential toxicity associated with systemic administration, and underscores the necessity for further research.

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Synthesis and Biocompatibility Studies of New Iminodiacetic Acid Derivatives

Cited by 5 publications

References 38 publications

Monitoring the hepatobiliary function using image techniques and labeled cholephilic compounds

Monitoring the hepatobiliary function using image techniques and labeled cholephilic compounds

Combined Thermodynamic, Theoretical, and Biological Study for Investigating N-(2-Acetamido)iminodiacetic Acid as a Potential Thorium Decorporation Agent

Biocompatibility Studies of Gadolinium Complexes with Iminodiacetic Acid Derivatives

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