Radiofluorination of PSMA-HBED via Al18F2+ Chelation and Biological Evaluations In Vitro

@article{Malik2015RadiofluorinationOP,
  title={Radiofluorination of PSMA-HBED via Al18F2+ Chelation and Biological Evaluations In Vitro},
  author={Noeen Malik and Benjamin Baur and Gordon Winter and Sven Norbert Reske and A. Beer and Christoph Solbach},
  journal={Molecular Imaging and Biology},
  year={2015},
  volume={17},
  pages={777-785}
}
PurposeGa-68-labeled prostate-specific membrane antigen (PSMA) ligands have been used clinically for positron emission tomography (PET) imaging of prostate cancer. However, F-18-labeled compounds offer several advantages, including the potential for delayed imaging, high starting activities enabling multidose preparation, and improved spatial resolution in PET. For F-18 labeling of peptides conjugated with a suitable chelator, a fast and feasible method is the use of [Al18F]2+. In the present… Expand
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In case of prostate cancer (PCa), Prostate Specific Membrane Antigen (PSMA) is shown to be a very valuable target for application by various ligands in clinical diagnosis and there are various compounds labeled with gallium-68 and fluorine-18. Expand
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  • E. Al-Momani, I. Israel, S. Samnick
  • Medicine
  • Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine
  • 2017
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Synthesis of an Al18F radiofluorinated GLU-UREA-LYS(AHX)-HBED-CC PSMA ligand in an automated synthesis platform
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References

SHOWING 1-10 OF 32 REFERENCES
Radiofluorination using aluminum-fluoride (Al18F)
TLDR
Because fluorine binds to aluminum, a procedure where the Al18F complex could be captured by a chelate, thereby greatly simplifying the way that imaging agents can be fluorinated for PET imaging is developed. Expand
Tetrafluorophenolate of HBED-CC: a versatile conjugation agent for 68Ga-labeled small recombinant antibodies
TLDR
The coupling of about one HBED-CC per antibody proved to be sufficient for efficient 68Ga labeling, pointing to the successful application of 68Ga for molecular imaging with small recombinant proteins. Expand
Comment on Afshar-Oromieh et al.: PET imaging with a [68Ga]gallium-labelled PSMA ligand for the diagnosis of prostate cancer: biodistribution in humans and first evaluation of tumour lesions
TLDR
In a study comprising 37 patients a discussion of 42 patients in the text needs clarification, the assumption that a prostate involved with prostate cancer and treated with local radiation therapy and androgen deprivation therapy can be regarded as a ‘normal prostate’ is not followed. Expand
One pot radiofluorination of a new potential PSMA ligand [Al18F]NOTA‐DUPA‐Pep
Up to now, many radiolabeled ligands targeting prostate-specific membrane antigen (PSMA) have been synthesized. To carry out radiofluorinations, there have been several approaches mainly involvingExpand
A Novel Facile Method of Labeling Octreotide with 18F-Fluorine
TLDR
NotA-octreotide could be labeled rapidly and efficiently with 18F using a 2-step, 1-pot method and was stable in vivo and showed rapid accretion in somatostatin receptor subtype 2–expressing AR42J tumors in nude mice. Expand
Radiosynthesis of a new PSMA targeting ligand ([18F]FPy-DUPA-Pep).
Due to the specificity of expression of PSMA (prostate specific membrane antigen) particularly in prostate cancer cells (e.g. LNCaP), numerous PSMA ligands have been synthesized until now. In theExpand
First Experience of 18F-Alfatide in Lung Cancer Patients Using a New Lyophilized Kit for Rapid Radiofluorination
TLDR
A simple lyophilized kit for labeling PRGD2 peptide (18F-AlF-NOTA-PRGD2, denoted as 18F-alfatide) using a fluoride–aluminum complex that significantly simplified the labeling procedure is developed and can be produced with excellent radiochemical yield and purity via a simple, 1-step, lyophile kit. Expand
PET imaging with a [68Ga]gallium-labelled PSMA ligand for the diagnosis of prostate cancer: biodistribution in humans and first evaluation of tumour lesions
TLDR
The biodistribution of the novel 68Ga-PSMA tracer and its ability to detect PC lesions was analysed in 37 patients to suggest that this novel tracer can detect PC relapses and metastases with high contrast. Expand
Design, synthesis, and preclinical evaluation of prostate-specific membrane antigen targeted (99m)Tc-radioimaging agents.
TLDR
Collectively, these high affinity, PSMA-specific radioimaging agents demonstrate significant potential for use in localizing prostate cancer masses, monitoring response to therapy, detecting prostate cancer recurrence following surgery, and selecting patients for subsequent PSma-targeted chemotherapy. Expand
New lyophilized kit for rapid radiofluorination of peptides.
TLDR
It is indicated that (18)F-labeled peptides can be reproducibly prepared as stable Al-F complexes with good radiochemical yield and high specific activity using a simple, one-step, lyophilized kit followed by a rapid purification by SPE that provides the (18]F-peptide ready for patient injection within 30 min. Expand
...
1
2
3
4
...