A gallium complex with a new tripodal tris-hydroxypyridinone for potential nuclear diagnostic imaging: solution and in vivo studies of 67Ga-labeled species

Chaves, Sı́lvia; Mendonça, Ana Catarina Fernandes; Marques, Sérgio M.; Prata, Maria João; Santos, Ana Catarina; Martins, André F.; Geraldes, Carlos F. G. C.; Santos, M. Amélia

doi:10.1016/j.jinorgbio.2010.09.012

Cited by 46 publications

(25 citation statements)

References 28 publications

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“…The signal that appeared at 9.7 ppm was assigned to the -HC= group and presence of aromatic ring was confirmed from a multiplet found in the range 6.0-7.0 ppm. Singlets obtained between 7.0 and 8.2 ppm correspond to the -OH groups of the aromatic ring [42]. In 13 C NMR spectra, the peak obtained at 164 ppm confirmed the presence of imine group in the ligand and signals near 53 and 55 ppm ensured the presence of methylene groups.…”

Section: Synthesis and Characterization Of Trenolmentioning

confidence: 87%

A Novel Tris(2-aminoethyl)amine Based Tripodal Ligand: Synthesis and Solution Coordination Studies with Trivalent Iron and Chromium

Baral

Gupta

Akbar

et al. 2016

Journal of Applied Chemistry

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A novel tris(2-aminoethyl)amine (TREN) based tripodal ligand TRENOL (L) has been synthesized and characterized by elemental analysis and UV-VIS, IR, 1H, and 13C NMR spectroscopic methods. The coordination behaviour of the ligand with H+ and trivalent metal ions, Fe(III) and Cr(III), was investigated in aqueous medium at 0.1 M KCl at 25±1°C by potentiometric and spectrophotometric studies. Tripodal ligand showed seven protonation constants in the adopted pH range 2–11 and its electronic spectra exhibited three bands at 216, 323, and 423 nm. Ligand formed various metal complex species of the type MLH5, MLH4, MLH3, MLH, and ML with trivalent metal ions. The determined values of the formation constants (for ML species) of the ligand with Fe(III) and Cr(III) were 24.19 and 18.64, respectively. Molecular modeling studies revealed that the metal complexes formed distorted octahedral geometry. Besides, ligand showed fluorescence at 496 nm when excited at 289 nm. The fluorescence behaviour of the ligand in the presence of Fe(III) ions showed noticeable quenching in comparison to the other metal ions at physiological pH (7.4). So, as per the outcomes of the present study, TRENOL has the potential to be used as the iron detector in environmental, agricultural, and medical fields.

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Section: Synthesis and Characterization Of Trenolmentioning

confidence: 87%

A Novel Tris(2-aminoethyl)amine Based Tripodal Ligand: Synthesis and Solution Coordination Studies with Trivalent Iron and Chromium

Baral

Gupta

Akbar

et al. 2016

Journal of Applied Chemistry

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“…There have been just few publications reporting on open-chain chelators and not all of them demonstrated desired properties. 67 Ga-labelled tripodal 3-hydroxy-4-pyridinone (1, NTP (PrHP) 3 , Figure 4) showed in vivo stability and fast renal excretion in healthy rats 114. Similar chelator, tripodaltris(hydroxypyridinone) (YM103), was functionalized with maleimide for the conjugation to proteins via Cys 115.…”

Section: Chemistry Of 68ga-based Imaging Agentsmentioning

confidence: 99%

Prospective of ⁶⁸Ga-Radiopharmaceutical Development

Velikyan¹

2014

Theranostics

274

249

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Positron Emission Tomography (PET) experienced accelerated development and has become an established method for medical research and clinical routine diagnostics on patient individualized basis. Development and availability of new radiopharmaceuticals specific for particular diseases is one of the driving forces of the expansion of clinical PET. The future development of the 68Ga-radiopharmaceuticals must be put in the context of several aspects such as role of PET in nuclear medicine, unmet medical needs, identification of new biomarkers, targets and corresponding ligands, production and availability of 68Ga, automation of the radiopharmaceutical production, progress of positron emission tomography technologies and image analysis methodologies for improved quantitation accuracy, PET radiopharmaceutical regulations as well as advances in radiopharmaceutical chemistry. The review presents the prospects of the 68Ga-based radiopharmaceutical development on the basis of the current status of these aspects as well as wide range and variety of imaging agents.

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“…The development of HOPO based chelators for nuclear imaging application is not new and several examples of chelators for 67 Ga or 68 Ga complexation have been reported over the recent years. 7,8,31 In line with these reported applications, bifunctional HOPO based chelators for 89 Zr complexation have recently been developed and studied in vivo with varying degrees of success. 30,32,33 The most stable to date, p -SCN-Bn-HOPO which is based on the 1,2-HOPO subunit, released a significantly lower fraction of the 89 Zr activity to the bone in comparison with the same antibody radiolabeled using DFB-SCN.…”

Section: Introductionmentioning

confidence: 99%

Investigation of the complexation of ^natZr(iv) and ⁸⁹Zr(iv) by hydroxypyridinones for the development of chelators for PET imaging applications

et al. 2017

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Three hydroxypyridinones (HOPOs) positional isomers - 1,2-HOPO (L1H) and its water soluble analogue (L1′H), 3,2-HOPO (L2H) and 3,4-HOPO (L3H)- have been investigated for the complexation of Zr(IV). Potentiometric and UV-Vis spectrometric studies show a higher thermodynamic stability for the formation of Zr(L1′)4 in comparison with Zr(L2)4 and Zr(L3)4 as well as a higher kinetic inertness in competition studies with EDTA or Fe3+ at radiotracer concentration with 89Zr. Besides the low pKa of L1H or L1′H (pKa = 5.01) in comparison with L2H and L3H (pKa = 8.83 and 9.55, respectively), the higher stability of Zr(L1′)4 can be attributed in part to the presence of the amide group next to the chelating oxygen that induces intramolecular H-bond and amide/π interactions that were observed by X-ray crystallography and confirmed by quantum chemical calculations. The data presented here indicates that the 1,2-HOPO L1′ exhibits the best characteristics for Zr(IV) complexation. However, 2,3-HOPO and 3,4-HOPO patterns, if appropriately tuned, for instance with the addition of an amide group as in the 1,2-HOPO ligand, may also become interesting alternatives for the design of Zr(IV) chelators with improved characteristics for application in nuclear imaging with 89Zr.

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A gallium complex with a new tripodal tris-hydroxypyridinone for potential nuclear diagnostic imaging: solution and in vivo studies of 67Ga-labeled species

Cited by 46 publications

References 28 publications

A Novel Tris(2-aminoethyl)amine Based Tripodal Ligand: Synthesis and Solution Coordination Studies with Trivalent Iron and Chromium

A Novel Tris(2-aminoethyl)amine Based Tripodal Ligand: Synthesis and Solution Coordination Studies with Trivalent Iron and Chromium

Prospective of ⁶⁸Ga-Radiopharmaceutical Development

Investigation of the complexation of ^natZr(iv) and ⁸⁹Zr(iv) by hydroxypyridinones for the development of chelators for PET imaging applications

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A gallium complex with a new tripodal tris-hydroxypyridinone for potential nuclear diagnostic imaging: solution and in vivo studies of 67Ga-labeled species

Cited by 46 publications

References 28 publications

A Novel Tris(2-aminoethyl)amine Based Tripodal Ligand: Synthesis and Solution Coordination Studies with Trivalent Iron and Chromium

A Novel Tris(2-aminoethyl)amine Based Tripodal Ligand: Synthesis and Solution Coordination Studies with Trivalent Iron and Chromium

Prospective of 68Ga-Radiopharmaceutical Development

Investigation of the complexation of natZr(iv) and 89Zr(iv) by hydroxypyridinones for the development of chelators for PET imaging applications

Contact Info

Product

Resources

About

Prospective of ⁶⁸Ga-Radiopharmaceutical Development

Investigation of the complexation of ^natZr(iv) and ⁸⁹Zr(iv) by hydroxypyridinones for the development of chelators for PET imaging applications