Correction to: Closing the gap between 19F and 18F chemistry

Ajenjo, Javier; Destro, Gianluca; Cornelissen, Bart; Gouverneur, Véronique

doi:10.1186/s41181-021-00152-x

Cited by 2 publications

(3 citation statements)

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“…Fluorine-18 can be introduced into macromolecules by means of several methods, the most frequent of which is via nucleophilic substitution on highly reactive leaving groups. This method occurs in “harsh” reaction conditions, often requiring temperature > 80 °C, and can’t be sustainable for fluorine-18 introduction into biologically active macromolecules, due to their inherent structural thermal sensitivity (Ajenjo et al 2021 ).…”

Section: Introductionmentioning

confidence: 99%

“…NODA, DOTA, NOTA) and non-cyclic (e.g. HBED) chelators (Ajenjo et al 2021 ; Al-Momani et al 2017 ; Malik et al 2015 ; Boschi et al 2016 ; Schmitt and Moreau 2023 ), although the best results were obtained with macrocyclic chelators such as NODA (pentadentate 1,4,7-triazacyclononane-1,4-diacetic acid) or NOTA (hexadentate ligand 1,4,7-triazacyclononane-1,4,7-triacetic acid). Indeed, they proved to chelate [ 18 F]AlF 2+ complex with high yields and stability in solution and in vivo (Schmitt and Moreau 2023 ; Liu et al 2019 ; Wang et al 2022 ).…”

Section: Introductionmentioning

confidence: 99%

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Automated radiosynthesis and preclinical evaluation of two new PSMA-617 derivatives radiolabelled via [18F]AlF2+ method

Iannone,

Valtorta,

Stucchi

et al. 2024

EJNMMI radiopharm. chem.

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Background In the last decade the development of new PSMA-ligand based radiopharmaceuticals for the imaging and therapy of prostate cancer has been a highly active and important area of research. The most promising derivative in terms of interaction with the antigen and clinical properties has been found to be “PSMA-617”, and its lutetium-177 radiolabelled version has recently been approved by EU and USA regulatory agencies for therapeutic purposes. For the above reasons, the development of new derivatives of PSMA-617 radiolabelled with fluorine-18 may still be of great interest. This paper proposes the comparison of two different PSMA-617 derivatives functionalized with NODA and RESCA chelators, respectively, radiolabelled via [18F]AlF2+ complexation. Results The organic synthesis of two PSMA-617 derivatives and their radiolabelling via [18F]AlF2+ complexation resulted to proceed efficiently and successfully. Moreover, stability in solution and in plasma has been evaluated. The whole radiosynthesis procedure has been fully automated, and the final products have been obtained with radiochemical yield and purity potentially suitable for clinical studies. The biodistribution of the two derivatives was performed both in prostate cancer and glioma tumour models. Compared with the reference [18F]F-PSMA-1007 and [18F]F-PSMA-617-RESCA, [18F]F-PSMA-617-NODA derivative showed a higher uptake in both tumors, faster clearance in non-target organs, and lower uptake in salivary glands. Conclusion PSMA-617 NODA and RESCA derivatives were radiolabelled successfully via [18F]AlF2+ chelation, the former being more stable in solution and human plasma. Moreover, preclinical biodistribution studies showed that [18F]F-PSMA-617-NODA might be of potential interest for clinical applications.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Automated radiosynthesis and preclinical evaluation of two new PSMA-617 derivatives radiolabelled via [18F]AlF2+ method

Iannone,

Valtorta,

Stucchi

et al. 2024

EJNMMI radiopharm. chem.

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“…1). Our group recently reported the radiosynthesis of [ 18 F]olaparib [21], [ 18 F]AZD2461 [22] and [ 18 F]rucaparib [23,24], demonstrating the strength of copper mediated radiofluorination as a useful methodology to overcome the challenge of C-18 F bond formation [25,26] and that radiolabelled versions of PARP inhibitors can prove to be useful PET imaging agents. [27][28] Here, we present the synthesis, radiosynthesis and preclinical evaluation of iodine-123 labelled rucaparib analogue, 8-[ 123 I]iodo-5-(4-((methylamino)methyl)phenyl)-2,3,4,6-tetrahydro-1H-azepino [5,4,3cd]indol-1-one, [ 123 I]GD1, as a potential radiotracer for RLT, via copper mediated radioiodination building on our previous work with [ 18 F]rucaparib.…”

Section: Introductionmentioning

confidence: 99%

A radioiodinated rucaparib analogue as an Auger electron emitter for cancer therapy.

Destro

Chen

Chang

et al. 2022

Preprint

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Introduction: Radioligand therapy (RLT) is an expanding field that has shown great potential in the fight against cancer. Radionuclides that can be carried by selective ligands such as antibodies, peptides, and small molecules targeting cancerous cells have demonstrated a clear improvement in the move towards precision medicine. Poly (ADP-ribose) polymerase (PARP) is a family of enzymes involved in DNA damage repair signalling pathway, with PARP inhibitors olaparib, talazoparib, niraparib, veliparib, and rucaparib having FDA approval for cancer therapy in routine clinical use. Based on our previous work with the radiolabelled PARP inhibitor [18F]rucaparib, we replaced the fluorine-18 moiety, used for PET imaging, with iodine-123, a radionuclide used for SPECT imaging and Auger electron therapy, resulting in 8-[123I]iodo-5-(4-((methylamino)methyl)phenyl)-2,3,4,6-tetrahydro-1H-azepino[5,4,3-cd]indol-1-one, ([123I]GD1), as a potential radiopharmaceutical for RLT. Methods: [123I]GD1 was synthesised via copper-mediated radioiodination from a selected boronic esters precursor. In vitro uptake, retention, blocking, and effects on clonogenic survival with [123I]GD1 treatment were tested in a panel of cancer cell lines. The enzymatic inhibition of PARP by GD1 was also tested in a cell-free system. The biodistribution of [123I]GD1 was investigated by SPECT/CT in mice following intravenous administration. Results: Cell-free enzymatic inhibition and in vitro blocking experiments confirmed a modest ability of GD1 to inhibit PARP-1, IC50= 239 nM. In vitro uptake of [123I]GD1 in different cell lines was dose-dependent, and the radiolabelled compound was retained in cells for more than 2 h. Significantly reduced clonogenic survival was observed in vitro after exposure of cells for 1 h with as low as 50 kBq of [123I]GD1. The biodistribution of [123I]GD1 was further characterized in vivo showing both renal and hepatobiliary clearance pathways with a biphasic blood clearance. Conclusion: We present the development of a new theragnostic agent based on the rucaparib scaffold and its evaluation in in vitro and in vivo models. The data reported show that [123I]GD1 may have the potential to be used as a theragnostic agent.

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Correction to: Closing the gap between 19F and 18F chemistry

Cited by 2 publications

References 1 publication

Automated radiosynthesis and preclinical evaluation of two new PSMA-617 derivatives radiolabelled via [18F]AlF2+ method

Automated radiosynthesis and preclinical evaluation of two new PSMA-617 derivatives radiolabelled via [18F]AlF2+ method

A radioiodinated rucaparib analogue as an Auger electron emitter for cancer therapy.

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