A Bidentate Terephthalamide Ligand, TAMmeg, as an Entry into Terephthalamide-Containing Therapeutic Iron Chelating Agents

Jurchen, Kristy M. Clarke; Raymond, Kenneth N.

doi:10.1021/ic051287+

Cited by 17 publications

(21 citation statements)

References 31 publications

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“…6 Moreover, ligand properties such as charge and solubility can be more easily modified using TAM units relative to other chelating units described in the literature. 6 c Additionally, unlike previously reported 89 Zr chelators, we incorporated into our ligand scaffolds a pendant arm containing a primary amine, which can be easily functionalized for conjugation to a variety of targeting ligands. These ligands were prepared by condensation of tetraamine and activated di-acid intermediates under high dilution (H.D.)…”

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confidence: 99%

Di-macrocyclic terephthalamide ligands as chelators for the PET radionuclide zirconium-89

et al. 2015

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The development of bifunctional chelators (BFCs) which can stably chelate zirconium-89 (89Zr) while being conjugated to targeting molecules is an area of active research. Herein we report the first octadentate terephthalamide ligands, which are easily radiolabeled with 89Zr and are highly stable in vitro. They represent a novel class of chelators, which are worthy of further development as BFCs for 89Zr.

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confidence: 99%

Di-macrocyclic terephthalamide ligands as chelators for the PET radionuclide zirconium-89

et al. 2015

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“…Herein, upon addition of increased concentration of Fe (III), an increased absorbance at λ 300 nm was observed, and concomitantly, the absorbance peak at λ 450 nm was compromised. It is well established that catecholate units in naturally occurring siderophores are efficient and necessary binding sites for ferric ion; , however, literature also reveals that synthetic siderophores − possessing a phenol substituent adjacent to a sp 2 hybridized nitrogen atom exhibits good iron chelation affinity. Thus, our prepared IL-2 and IL-3 comprising similar binding sites (Figure ) also shows good affinity toward ferric ion selectively as compared with other cations as evidenced by UV–visible absorption spectroscopy.…”

Section: Resultsmentioning

confidence: 99%

Development of Biological Self-Cleaning Wound-Dressing Gauze for the Treatment of Bacterial Infection

Bains

Singh

Kaur

et al. 2018

ACS Sustainable Chem. Eng.

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Microorganisms, dirt, and other air pollutants are major problems in textiles, which can generate an unpleasant odor during their growth. Herein, we have developed some novel antibacterial benzimidazolium-based dipodal ionic liquids that act as iron chelators, and they were loaded onto the wound-dressing gauze to enhance their antimicrobial properties for biomedical applications. The metal binding affinity of the synthesized ionic liquids was evaluated by UV–visible absorption and fluorescence spectroscopy, which reveals its selectivity toward Fe (III) ion. It is well-established that almost all bacteria require Fe (III) for survival and growth. To compete successfully for this essential nutrient, bacteria developed very efficient Fe (III) uptake mechanisms based on high-affinity Fe (III) chelators, so-called siderophores. Thus, keeping this in mind, all the prepared ionic-liquid-based iron chelators have been evaluated for their in vitro antibacterial activity against various pathogenic bacterial strains by colony forming unit (CFU) assay, and the MICs were determined by a broth microdilution method. The mechanism of action has also been explored by atomic force microscopy (AFM) and scanning electron microscopy (SEM), which reveals the bacterial cell wall deformity and cell wall rupturing that may lead to bacteria cell death. The most potent antibacterial compound, IL-3, was also investigated for its cytotoxicity against mammalian HeLa cell line and found to be nontoxic (IC50 > 100 μM). Further, the IL-3-coated wound-dressing gauze has been developed, fully characterized, and investigated against some Gram-positive and Gram-negative bacteria. Moreover, the IL-3-coated gauze was also evaluated for its hemostatic potential, and results reveal that the developed gauze shortens the time period required for blood clotting in comparison to simple dressing gauze and pledget that are commonly used in clinics. Thus, the potential antibacterial and hemostatic results exhibited by developed IL-3-coated gauze make it a useful tool that can be used in wards, ICU, and particularly, by military persons in war front areas.

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“…Thus, 1 contains binding units similar to siderophores, which are the iron chelating compounds secreted by microorganisms to facilitate the active transport of iron [11]. It has been demonstrated that many siderophores and iron chelating agents comprise a phenol substituent adjacent to a sp 2 hybridised nitrogen atom as depicted in structure 2 (Scheme 1) [12][13][14].…”

Section: Resultsmentioning

confidence: 99%

A New Fluorescent Sensor for the Determination of Iron(III) in Semi-Aqueous Solution

Casanueva-Marenco

Fowley²,

Hyland³

et al. 2011

J Fluoresc

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A simple fluorescent sensor 1 has been developed for the recognition of Fe(III) in semi-aqueous solution at pH 7.0. The sensor, containing two Schiff base type receptors directly connected to naphthalene fluorophores, shows a concentration dependent decrease in emission intensity upon Fe(III) addition. The sensor was selective for Fe(III) over other metal ions and can measure Fe(III) ion concentration between 0.05 and 0.12 mM. The binding stoichiometry was established as 1:1 (host: guest) with a binding constant (Logβ) of 4.01. Furthermore, the addition of Fe(III) to a solution of 1 caused a colour change from light yellow to colourless meaning 1 is also capable of detecting Fe(III) by the naked eye.

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A Bidentate Terephthalamide Ligand, TAMmeg, as an Entry into Terephthalamide-Containing Therapeutic Iron Chelating Agents

Cited by 17 publications

References 31 publications

Di-macrocyclic terephthalamide ligands as chelators for the PET radionuclide zirconium-89

Di-macrocyclic terephthalamide ligands as chelators for the PET radionuclide zirconium-89

Development of Biological Self-Cleaning Wound-Dressing Gauze for the Treatment of Bacterial Infection

A New Fluorescent Sensor for the Determination of Iron(III) in Semi-Aqueous Solution

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