Recent Advances in Synthetic Methods for Radioiodination

Dubost, Emmanuelle; McErlain, Holly; Babin, Victor; Sutherland, Andrew; Cailly, Thomas

doi:10.1021/acs.joc.0c00644

Cited by 48 publications

(49 citation statements)

References 57 publications

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“…The process of electrophilic substitution in the direct labeling method involved two processes, mono and diodinated, which resulted in 2 forms. The I + is attached at the ortho position because it is supported by the presence of a hydroxy group (-OH) with large electron-withdrawing properties [ 21 , 22 ]. Estradiol labeled with the complexes by electrophilic substitution was presented in ( Figure 2 ).…”

Section: Discussionmentioning

confidence: 99%

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Synthesis, stability, and cellular uptake of 131I-estradiol against MCF7 and T-47D human cell lines as a radioligand for binding assay

Daruwati

Gwiharto

Kurniawan

et al. 2021

Heliyon

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Estradiol is a steroid hormone that works as an agonist estrogen receptor (ER). This compound is widely used as a ligand and bind specifically to the ERα. Radioligand binding assay is an in vitro method for drug development from natural products by synthesizing estradiol through radiolabeling using the radioiodination method. Synthesis of 131 I-estradiol was perfomed by direct method using chloramine T as an oxidizer and by indirect labeling using 131 I-histamine. The purity of chemical was determined by thin-layer chromatography and paper electrophoresis, as well as its stability for 30 days of storage in refrigerator, freezer and room temperature. The cellular uptake test of the radioligands from both methods was carried out with MCF7 and T-47D cell lines at 60 min. The results exhibited that 131 I-estradiol was succesfully obtained with radiochemical purity greater than 95% and more stable in the refrigerator until 21 days than freezer and room temperature. 131 I-estradiol and 131 I-his-estradiol were internalized higher in T-47D cells than MCF7 cells (44.34 ± 5.93% vs. 17.27 ± 1.71% and 45.34 ± 6.42% vs. 4.92 ± 1.59%, respectively). Furthermore, the radioligands can be used to binding assay in determining the agonist or antagonist to ER of new drugs development.

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Section: Discussionmentioning

confidence: 99%

“…The advantages of RBA are measure at low receptor concentrations, selective and sensitive [ 14 ]. Estradiol is a compound that can be easily to radiolabel and developed using 125/131 Iodine or Tritium ( 3 H) [ 15 ]. This radioligand is paired with ER and must be compatible and have the same action or agonist with the receptor [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, stability, and cellular uptake of 131I-estradiol against MCF7 and T-47D human cell lines as a radioligand for binding assay

Daruwati

Gwiharto

Kurniawan

et al. 2021

Heliyon

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“…Due to the low-energy radiation and the long half-life, iodine-125 is the most suitable isotope to serve as a surrogate of all the other iodine radionuclides in pre-clinical research and drugs development. Labelling with iodine-125 normally involves incorporation of the radionuclide into tyrosyl- or histidyl-like residues belonging to the molecular structure of interest [ 54 ].…”

Section: Radiohalogenated Curcumin Derivativesmentioning

confidence: 99%

Applications of Radiolabelled Curcumin and Its Derivatives in Medicinal Chemistry

Mari

Carrozza

Ferrari

et al. 2021

IJMS

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Curcumin is a natural occurring molecule that has aroused much interest among researchers over the years due to its pleiotropic set of biological properties. In the nuclear medicine field, radiolabelled curcumin and curcumin derivatives have been studied as potential radiotracers for the early diagnosis of Alzheimer’s disease and cancer. In the present review, the synthetic pathways, labelling methods and the preclinical investigations involving these radioactive compounds are treated. The studies entailed chemical modifications for enhancing curcumin stability, as well as its functionalisation for the labelling with several radiohalogens or metal radionuclides (fluorine-18, technetium-99m, gallium-68, etc.). Although some drawbacks have yet to be addressed, and none of the radiolabelled curcuminoids have so far achieved clinical application, the studies performed hitherto provide useful insights and lay the foundation for further developments.

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“…Recently, radioiodination of a variety of aromatic compounds was found to proceed in high yield under mild conditions starting from aryl boronic acids or pinacol boronic esters using [Cu(OTf) 2 (py) 4 ] as well [67,68,83,84].…”

Section: Radioiodinationmentioning

confidence: 99%

Radiolabeled Silicon-Rhodamines as Bimodal PET/SPECT-NIR Imaging Agents

et al. 2021

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Radiolabeled fluorescent dyes are decisive for bimodal imaging as well as highly in demand for nuclear- and optical imaging. Silicon-rhodamines (SiRs) show unique near-infrared (NIR) optical properties, large quantum yields and extinction coefficients as well as high photostability. Here, we describe the synthesis, characterization and radiolabeling of novel NIR absorbing and emitting fluorophores from the silicon-rhodamine family for use in optical imaging (OI) combined with positron emission tomography (PET) or single photon emission computed tomography (SPECT), respectively. The presented photostable SiRs were characterized using NMR-, UV-Vis-NIR-spectroscopy and mass spectrometry. Moreover, the radiolabeling conditions using fluorine-18 or iodine-123 were extensively explored. After optimization, the radiofluorinated NIR imaging agents were obtained with radiochemical conversions (RCC) up to 70% and isolated radiochemical yields (RCY) up to 54% at molar activities of g.t. 70 GBq/µmol. Radioiodination delivered RCCs over 92% and allowed to isolate the 123I-labeled product in RCY of 54% at a molar activity of g.t. 7.6 TBq/µmol. The radiofluorinated SiRs exhibit in vitro stabilities g.t. 70% after two hours in human serum. The first described radiolabeled SiRs are a promising step toward their further development as multimodal PET/SPECT-NIR imaging agents for planning and subsequent imaging-guided oncological surgery.

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Recent Advances in Synthetic Methods for Radioiodination

Cited by 48 publications

References 57 publications

Synthesis, stability, and cellular uptake of 131I-estradiol against MCF7 and T-47D human cell lines as a radioligand for binding assay

Synthesis, stability, and cellular uptake of 131I-estradiol against MCF7 and T-47D human cell lines as a radioligand for binding assay

Applications of Radiolabelled Curcumin and Its Derivatives in Medicinal Chemistry

Radiolabeled Silicon-Rhodamines as Bimodal PET/SPECT-NIR Imaging Agents

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