650 results match your criteria Journal of Labelled Compounds and Radiopharmaceuticals[Journal]


F-Labeled benzylpiperazine derivatives as highly selective ligands for imaging σ receptor with positron emission tomography.

J Labelled Comp Radiopharm 2019 Apr 16. Epub 2019 Apr 16.

Key Laboratory of Radiopharmaceuticals (Beijing Normal University), Ministry of Education, College of Chemistry, Beijing Normal University, Beijing, China.

We report the design, synthesis and evaluation of a new series of benzylpiperazine derivatives as selective σ receptor ligands. All seven ligands possessed low nanomolar affinity for σ receptors (K (σ ) = 0.31-4. Read More

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http://dx.doi.org/10.1002/jlcr.3738DOI Listing

Targeted Cu-labeled gold nanoparticles for dual imaging with positron emission tomography and optical imaging.

J Labelled Comp Radiopharm 2019 Apr 12. Epub 2019 Apr 12.

Molecular Imaging and Radiochemistry, Department of Clinical Radiology and Nuclear Medicine, Medical Faculty Mannheim of Heidelberg University, Mannheim, Germany.

Gold nanoparticles (AuNPs) have been used for many years in cancer treatment mainly for brachytherapy, but in the last 15 years the focus has shifted to the development of ultra-small target-specific AuNPs with homogeneous size and, ultimately, tailored shapes for use in various imaging modalities such as CT, Raman, or photoacoustic imaging. Here, we report on the development of tumor-specific AuNPs as diagnostic tools intended for the dual detection of prostate cancer via optical imaging (OI) and positron emission tomography (PET). The AuNPs were decorated with a near-infrared dye and NODAGA chelator for complexation with radiometals. Read More

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http://doi.wiley.com/10.1002/jlcr.3736
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http://dx.doi.org/10.1002/jlcr.3736DOI Listing
April 2019
2 Reads

Designing Tracers for PET Imaging of the Urokinase-type Plasminogen Activator Receptor from a Cyclic uPA-derived Peptide - First in Vitro Evaluations.

J Labelled Comp Radiopharm 2019 Apr 10. Epub 2019 Apr 10.

Division of Radiopharmaceutical Chemistry, German Cancer Research Center (DKFZ), Heidelberg, Germany.

The treatment of cancer remains a major challenge, especially after tumour cell dissemination and metastases formation. Expression of the urokinase-type plasminogen activation system including urokinase (uPA) and its receptor (uPAR) has been associated with the complex process of cell migration, a tumour's invasive potential as well as a reduced overall- and disease-free survival of patients with solid cancers and haematological disorders. A cyclic peptide cyclo[21,29][d-Cys ,Cys ]-uPA was designed from the growth factor-like domain (GFD) of urokinase whose binding to uPAR was found to inhibit tumour growth and spread of human ovarian cancer cells in mice. Read More

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http://dx.doi.org/10.1002/jlcr.3735DOI Listing
April 2019
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Facile radiolabeling optimization process via design of experiments and an intelligent optimization algorithm: Application for omeprazole radioiodination.

J Labelled Comp Radiopharm 2019 Apr 10. Epub 2019 Apr 10.

Radioactive Waste Management Department, Hot Labs. Center, Atomic Energy Authority, Cairo, Egypt.

The major uses of radiopharmaceuticals (RP) in clinical areas are diagnosis and/or therapy. The present study aimed to utilize the application of fractional factorial design analysis (FFDA) coupled with particle swarm optimization algorithm (PSO) to assess the optimization of RP production process. In this regard, omeprazole (OMP) which is gastric parietal cell proton pump inhibitor (PPI) was radiolabeled with iodine-125 ( I) isotope in order to be used as a radiotracer for stomach imaging. Read More

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http://dx.doi.org/10.1002/jlcr.3734DOI Listing
April 2019
2 Reads

Comparative evaluation of the new GRPR-antagonist In-SB9 and In-AMBA in prostate cancer models - Implications of in vivo stability.

J Labelled Comp Radiopharm 2019 Apr 8. Epub 2019 Apr 8.

Molecular Radiopharmacy, INRASTES, NCSR "Demokritos", Athens, Greece.

Gastrin-releasing peptide receptors (GRPRs) are overexpressed in prostate cancer, representing attractive targets for diagnosis and therapy with bombesin (BBN)-like radioligands. GRPR-antagonists have lately attracted much attention owing to inherent biosafety and attractive pharmacokinetics. We herein present the GRPR-antagonist SB9 structurally resembling the known BBN-based agonist AMBA (SB9 = [Leu NHEt-desMet ]AMBA). Read More

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http://dx.doi.org/10.1002/jlcr.3733DOI Listing

Fine-tuning of the automated [ F]PSMA-1007 radiosynthesis.

J Labelled Comp Radiopharm 2019 Apr 3. Epub 2019 Apr 3.

Cyclotron/Radiochemistry/MicroPET Unit, Hadassah Hebrew University Hospital, Hadassah Medical Organization, Jerusalem, Israel.

Radiolabeled prostate-specific membrane antigen (PSMA) targeting PET-tracers have become desirable radiopharmaceuticals for the imaging of prostate cancer (PC). Recently, the PET radiotracer [ F]PSMA-1007 was introduced as an alternative to [ Ga]Ga-PSMA-11, for staging and diagnosing biochemically recurrent PC. We incorporated a one-step procedure for [ F]PSMA-1007 radiosynthesis, using both Synthra RNplus and GE TRACERlab FxFN automated modules, in accordance with the recently described radiolabeling procedure. Read More

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http://dx.doi.org/10.1002/jlcr.3732DOI Listing
April 2019
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Synthesis, H-labelling and in vitro evaluation of a substituted dipiperidine alcohol as a potential ligand for chemokine receptor 2.

J Labelled Comp Radiopharm 2019 Apr 1. Epub 2019 Apr 1.

Early Chemical Development, Pharmaceutical Science, IMED Biotech Unit, AstraZeneca, Gothenburg, Sweden.

The immune system is implicated in the pathology of neurodegenerative disorders. The chemokine receptor 2 (CCR2) is one of the key targets involved in the activation of the immune system. A suitable ligand for CCR2 could be a useful tool to study immune activation in central nervous system (CNS) disorders. Read More

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http://dx.doi.org/10.1002/jlcr.3731DOI Listing
April 2019
3 Reads

Implementation of a new separation method to produce qualitatively improved Cu.

J Labelled Comp Radiopharm 2019 Mar 27. Epub 2019 Mar 27.

Center for Radiopharmaceutical Sciences ETH-PSI-USZ, Paul Scherrer Institute, Villigen, Switzerland.

Background: Cu (T = 12.7 h) is an important radionuclide for diagnostic purposes and used for positron emission tomography (PET). A previous method utilized at Paul Scherrer Institute (PSI) proved to be unreliable and, while a method using anion exchange chromatography is a popular choice worldwide, it was felt a different approach was required to obtain a robust chemical separation method. Read More

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http://dx.doi.org/10.1002/jlcr.3730DOI Listing

Radiochemical and radiopharmacological characterization of a Cu-labeled α-MSH analog conjugated with different chelators.

J Labelled Comp Radiopharm 2019 Mar 26. Epub 2019 Mar 26.

Helmholtz-Zentrum Dresden-Rossendorf, Institute of Radiopharmaceutical Cancer Research, Dresden, Germany.

Radiolabeled α-melanocyte stimulating hormone (α-MSH) derivatives have a high potential for diagnosis and treatment of melanoma, due to high specificity and binding affinity to the melanocortin-1 receptor (MC1R). Hence, the α-MSH-derived peptide NAP-NS1 with a β-Ala linker (ε-Ahx-β-Ala-Nle-Asp-His-D-Phe-Arg-Trp-Gly-NH ) was conjugated to different chelators: either to NOTA (p-SCN-Bn-1,4,7-triazacyclononane-1,4,7-triacetic acid), to a hexadentate bispidine carbonate derivative (dimethyl-9-(((4-nitrophenoxy)carbonyl)oxy)-2,4-di (pyridin-2-yl)-3,7-bis (pyridin-2-ylmethyl)-3,7-diazabicyclo[3.3. Read More

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http://dx.doi.org/10.1002/jlcr.3728DOI Listing

Synthesis and preliminary radiopharmacological characterisation of an C-labelled azadipeptide nitrile as potential PET tracer for imaging of cysteine cathepsins.

J Labelled Comp Radiopharm 2019 Mar 26. Epub 2019 Mar 26.

Institute of Radiopharmaceutical Cancer Research, Helmholtz-Zentrum Dresden-Rossendorf, Dresden, Germany.

An O-methyltyrosine-containing azadipeptide nitrile was synthesised and investigated for its inhibitory activity towards cathepsins L, S, K and B. Labelling with carbon-11 was accomplished by reaction of the corresponding phenolic precursor with [ C]methyl iodide starting from cyclotron-produced [ C]methane. Radiopharmacological evaluation of the resulting radiotracer in a mouse xenograft model derived from a mammary tumour cell line by small animal PET imaging indicates tumour targeting with complex pharmacokinetics. Read More

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http://dx.doi.org/10.1002/jlcr.3729DOI Listing
March 2019
2 Reads

Theranostic CAR T cell Targeting, a brief review.

J Labelled Comp Radiopharm 2019 Mar 19. Epub 2019 Mar 19.

Helmholtz-Zentrum Dresden-Rossendorf (HZDR), Institute of Radiopharmaceutical Cancer Research, Dresden, Germany.

More than hundred years ago Paul Ehrlich postulated that our immune system should be able to recognize tumor cells. Just recently the development of check point inhibitors, bispecific antibodies (bsAbs) and T cells genetically modified to express chimeric antigen receptors (CARs) underlines the true power of our immune system. T cells genetically modified with CARs can lead to complete remission of malignant hematologic diseases. Read More

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http://dx.doi.org/10.1002/jlcr.3727DOI Listing
March 2019
1 Read

Synthesis of Stable Isotope Labeled Chloroquine, Amodiaquine and Their Metabolites.

J Labelled Comp Radiopharm 2019 Mar 18. Epub 2019 Mar 18.

Bioenergy and Biome Sciences, Group-B11, Bioscience Division, Los Alamos National Laboratory, Los Alamos, NM.

Anti-malaria drugs chloroquine, amodiaquine and their metabolites were stable isotope labeled with C and N starting from uniformly C labeled benzene and N labeled potassium nitrate to give M+7 isotopomers. Chloroquine, and its metabolites were prepared from 7-chloro-1,2,3,4-tetrahydroquinolin-4-one through addition to the carbonyl with the corresponding amines; and the amodiaquine and its metabolites were prepared from 4,7-dichloroquinoline in a selective aryl-halogen exchange with the corresponding amines. Read More

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http://dx.doi.org/10.1002/jlcr.3721DOI Listing
March 2019
1.187 Impact Factor

Initial experience in synthesis of (2S,4R)-4-[ F]fluoroglutamine for clinical application.

J Labelled Comp Radiopharm 2019 Mar 12. Epub 2019 Mar 12.

Beijing Institute of Brain Disorders, Capital Medical University, Beijing, China.

We report initial experience in synthesis of (2S,4R)-4-[ F]fluoroglutamine, [ F]FGln, which has been used as a tool for monitoring glutamine metabolism in cancer patients. [ F]FGln was prepared by a fully automated PET-MF-2V-IT-I synthesizer under GMP-compliant conditions for routine clinical studies. The total radiosynthesis time was about 65 minutes, the decay-corrected radiochemical yield was 18. Read More

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http://dx.doi.org/10.1002/jlcr.3719DOI Listing
March 2019
7 Reads

Synthesis and pharmacological evaluation of fluorinated benzo[7]annulen-7-amines as GluN2B-selective NMDA receptor antagonists.

J Labelled Comp Radiopharm 2019 Mar 8. Epub 2019 Mar 8.

Institut für Pharmazeutische und Medizinische Chemie der Universität Münster, Münster, Germany.

Due to their neuroprotective potential, GluN2B-selective ligands are of great interest for the treatment of various neurological and neurodegenerative disorders. Fluorinated benzo[7]annulen-7-amines, capable for PET, were synthesized by combining fluorinated phenylalkylamines with differently substituted ketones. Relationships between substitution pattern and GluN2B affinity as well as selectivity towards σ and σ receptors were investigated. Read More

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http://dx.doi.org/10.1002/jlcr.3718DOI Listing
March 2019
1 Read
1.187 Impact Factor

Radiosynthesis of the norepinephrine transporter tracer [ F]NS12137 via copper-mediated F-labelling.

J Labelled Comp Radiopharm 2019 Mar 6. Epub 2019 Mar 6.

Radiopharmaceutical Chemistry Laboratory, Turku PET Centre, University of Turku, Turku, Finland.

[ F]NS12137 (exo-3-[(6-[ F]fluoro-2-pyridyl)oxy]8-azabicyclo[3.2.1]octane) is a highly selective norepinephrine transporter (NET) tracer. Read More

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http://dx.doi.org/10.1002/jlcr.3717DOI Listing
March 2019
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Synthesis of deuterium-labelled amlexanox and its metabolic stability against mouse, rat, and human microsomes.

J Labelled Comp Radiopharm 2019 Mar 3. Epub 2019 Mar 3.

Department of Medicinal Chemistry, University of Michigan, Ann Arbor, Michigan, USA.

As part of a program toward making analogues of amlexanox (1), currently under clinical investigation for the treatment of type 2 diabetes and obesity, we have synthesized derivative 5 in which deuterium has been introduced into two sites of metabolism on the C-7 isopropyl function of amlexanox. The synthesis of 5 was completed in an efficient three-step process utilizing reduction of key olefin 7b to 8 by Wilkinson's catalyst to provide specific incorporation of di-deuterium across the double bond. Compound 5 displayed nearly equivalent potency to amlexanox (IC , 1. Read More

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http://doi.wiley.com/10.1002/jlcr.3716
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http://dx.doi.org/10.1002/jlcr.3716DOI Listing
March 2019
8 Reads
1.187 Impact Factor

Synthesis and biological evaluation of deuterated sofosbuvir analogs as HCV NS5B inhibitors with enhanced pharmacokinetic properties.

J Labelled Comp Radiopharm 2019 Mar 3. Epub 2019 Mar 3.

Jiangsu Key Laboratory of Targeted Antiviral Research, Chia Tai Tianqing Pharmaceutical Group Co., LTD, Nanjing, Jiangsu Province, China.

A series of deuterated sofosbuvir analogs were designed and prepared with the aim of improving their pharmacokinetic properties. The devised synthetic routes allow for site-selective deuterium incorporation with high levels of isotopic purity. As expected, the deuterated analogs (37-44) are as efficacious as sofosbuvir when tested in vitro inhibition of viral replication (replicon) assays. Read More

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http://dx.doi.org/10.1002/jlcr.3715DOI Listing
March 2019
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Synthesis of Di-docosahexaenoyl (C22:6)-bis (monoacyl-glycerol) phosphate in unlabeled and C-13 labeled forms for use as a biomarker of drug induced phospholipidosis.

J Labelled Comp Radiopharm 2019 Feb 21. Epub 2019 Feb 21.

Early Chemical Development, Pharmaceutical Sciences, IMED Biotech Unit, AstraZeneca, Göteborg, Sweden.

Di-docosahexaenoyl (C22:6)-bis (monoacylglycerol) phosphate (BMP) has been identified as a promising biomarker for drug-induced phospholipidosis (DIPL). Both unlabeled and stable isotope labeled versions of BMP were desired for use as internal standards. Isopropylideneglycerol was converted to 4-methoxyphenyldiphenylmethyl-3-PMB-glycerol in three steps. Read More

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http://dx.doi.org/10.1002/jlcr.3714DOI Listing
February 2019
1 Read
1.187 Impact Factor

Clinical translation of theranostic radiopharmaceuticals: Current regulatory status and recent examples.

J Labelled Comp Radiopharm 2019 Feb 11. Epub 2019 Feb 11.

Department of Nuclear Medicine, Medical University Innsbruck, Innsbruck, Austria.

With the development of ever more radiopharmaceuticals suitable for theranostic applications, translation of novel compounds from the preclinical stage towards clinical application becomes a bottleneck for the advances in Nuclear Medicine. This review article summarizes the current regulatory framework for clinical trials with radiopharmaceuticals in the European Union, provides a general overview of the documentation required, and addresses quality, safety, and clinical aspects to be considered. By using a recent successful example of translating a theranostic peptide radioligand, namely In-CP04, which targets receptors expressed in medullary thyroid carcinoma, the pathway from the preclinical development over establishing the required pharmaceutical documentation to designing and submitting a clinical trial is reviewed. Read More

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http://dx.doi.org/10.1002/jlcr.3712DOI Listing
February 2019
4 Reads

A simple and efficient automated cGMP-compliant radiosynthesis of [ C]metomidate using solid phase extraction cartridge purification.

J Labelled Comp Radiopharm 2019 Apr 27;62(4):190-197. Epub 2019 Feb 27.

Wolfson Brain Imaging Centre, Department of Clinical Neurosciences, University of Cambridge, Addenbrooke's Hospital, Cambridge, CB2 0QQ, UK.

[ C]metomidate ([ C]MTO) is a radiotracer widely used to detect disorders of adrenocortical origin by positron emission tomography (PET) imaging. [ C]MTO PET/computed tomography (PET/CT) is considered a sensitive and specific noninvasive alternative to adrenal vein sampling (AVS) in the management of primary hyperaldosteronism (PHA). Herein, we report a reliable automated procedure for the routine manufacturing of [ C]MTO in current good manufacturing practice (cGMP) conditions on the commercial Synthra MeI Loop Vessel synthesizer. Read More

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http://dx.doi.org/10.1002/jlcr.3711DOI Listing
April 2019
6 Reads
1.187 Impact Factor

Automated production of [ Ga]Ga-DOTANOC and [ Ga]Ga-PSMA-11 using a TRACERlab FX synthesis module.

J Labelled Comp Radiopharm 2019 Mar 5;62(3):146-153. Epub 2019 Feb 5.

Departamento de Radiología y Medicina Física. Centro de Investigaciones Médico-Sanitarias, Universidad de Málaga, Málaga, Spain.

The interest in gallium-68 labelled positron-emission tomography probes continues to increase around the world. However, one of the barriers for routine clinical use is the cost of the automated synthesis units for relatively simple labelling procedures. Herein, we describe the adaptation of a TRACERlab FX synthesis module for the automated production of gallium-68 radiopharmaceuticals using a cation-exchange cartridge for postprocessing of the Ge/ Ga generator eluate. Read More

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http://doi.wiley.com/10.1002/jlcr.3706
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http://dx.doi.org/10.1002/jlcr.3706DOI Listing
March 2019
8 Reads

New Tc(CO) -radiolabeled arylpiperazine pharmacophore as potent 5HT serotonin receptor radiotracer: Docking studies, chemical synthesis, radiolabeling, and biological evaluation.

J Labelled Comp Radiopharm 2019 Apr 12;62(4):166-177. Epub 2019 Mar 12.

Department of Nuclear Medicine, School of Medicine, Rajaie Cardiovascular, Medical & Research Center, Iran University of Medical Sciences, Tehran, Iran.

In spite of previous efforts, there is lack of a radiotracer for imaging the 5HT receptor density in human brain, which is involved in several neurological brain disorders. The aim of this study was to prepare a new derivative of 1-(2-methoxyphenyl)piperazine (MPP) as a main chemical structure of 5HT receptor antagonist with 3-carbon linker and radiolabeled by [ Tc][Tc(CO) (H O) ] precursor. Docking studies before chemical synthesis showed similar fashion of interaction for both WAY100635 (potent 5HT receptor antagonist) and new designed ligand, despite of addition of Tc(CO) group in the structure of new ligand. Read More

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http://dx.doi.org/10.1002/jlcr.3709DOI Listing
April 2019
1 Read

Ce-141-labeled DOTMP: A theranostic option in management of pain due to skeletal metastases.

J Labelled Comp Radiopharm 2019 Apr 27;62(4):178-189. Epub 2019 Feb 27.

Radiopharmaceuticals Division, Bhabha Atomic Research Centre, Mumbai, India.

Owing to its favorable radioactive decay characteristics (T  = 32.51 d, E [max] = 434.6 keV [70. Read More

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http://dx.doi.org/10.1002/jlcr.3710DOI Listing
April 2019
2 Reads
1.187 Impact Factor

Preparation of Lu-labeled Nimotuzumab for radioimmunotherapy of EGFR-positive cancers: Comparison of DOTA and CHX-A″-DTPA as bifunctional chelators.

J Labelled Comp Radiopharm 2019 Apr 17;62(4):158-165. Epub 2019 Feb 17.

Radiopharmaceuticals Division, Bhabha Atomic Research Centre, Mumbai, India.

This study was aimed at evaluating the role of bifunctional chelators DOTA-NCS and CHX-A″-DTPA-NCS used for conjugating Lu with Nimotuzumab on the radiochemical yields, purity, in vitro stability, and specificity of the radioimmunoconjugates to EGFR. Two immunoconjugates were prepared wherein Nimotuzumab was conjugated with the acyclic ligand p-NCS-Bn-CHX-A″-DTPA and macrocyclic ligand p-NCS-Bn-DOTA. These were radiolabeled with Lu, purified on PD-10 column, and characterized by SE-HPLC. Read More

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http://dx.doi.org/10.1002/jlcr.3707DOI Listing
April 2019
1 Read
1.187 Impact Factor

Access to F-labelled isoxazoles by ruthenium-promoted 1,3-dipolar cycloaddition of 4-[ F]fluoro-N-hydroxybenzimidoyl chloride with alkynes.

J Labelled Comp Radiopharm 2019 Jan 20. Epub 2019 Jan 20.

Institute of Radiopharmaceutical Cancer Research, Helmholtz-Zentrum Dresden-Rossendorf, Dresden, Germany.

4-[ F]Fluoro-N-hydroxybenzimidoyl chloride ( FBIC), an F-labelled aromatic nitrile oxide, was developed as building block for Ru-promoted 1,3-dipolar cycloaddition with alkynes. FBIC is obtained in a one-pot synthesis in up to 84% radiochemical yield (RCY) starting from [ F]fluoride with 4-[ F]fluorobenzaldehyde ( FBA) and 4-[ F]fluorobenzaldehyde oxime ( FBAO) as intermediates, by reaction of FBAO with N-chlorosuccinimide (NCS). FBIC was found to be a suitable and stable synthon to give access to F-labelled 3,4-diarylsubstituted isoxazoles by [Cp*RuCl(cod)]-catalysed 1,3-dipolar cycloaddition with various alkynes. Read More

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http://dx.doi.org/10.1002/jlcr.3708DOI Listing
January 2019
3 Reads

An azeotropic drying-free approach for copper-mediated radiofluorination without addition of base.

J Labelled Comp Radiopharm 2019 Mar 20;62(3):139-145. Epub 2019 Feb 20.

Imaging Probe Development Center, National Heart, Lung, and Blood Institute, National Institutes of Health, Rockville, Maryland.

Copper-mediated radiofluorination provides a quick and versatile approach for F-labeling of arenes and heteroarenes. However, this method is known to be base sensitive, which has been a barrier for preparative scale radiosynthesis. In this report, we provide an approach for copper-mediated radiofluorination without azeotropic drying or adding a base. Read More

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http://dx.doi.org/10.1002/jlcr.3705DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6428597PMC
March 2019
2 Reads

Efficient gallium-68 radiolabeling reaction of DOTA derivatives using a resonant-type microwave reactor.

J Labelled Comp Radiopharm 2019 Mar 16;62(3):132-138. Epub 2019 Jan 16.

Department of Analytical and Bioinorganic Chemistry, Kyoto Pharmaceutical University, Kyoto, Japan.

Gallium-68 ( Ga, t  = 68 min) can be easily obtained from a Ge/ Ga generator, and several such systems are commercially available. The use of positron emission tomography (PET) imaging using Ga-labeled radiopharmaceuticals is expected to increase in both preclinical and clinical settings. However, the chelation between a Ga cation and the bifunctional macrocyclic chelates that are used for labeling bioactive substances, such as 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA), requires a relatively long reaction time and high temperature to achieve a high radiochemical yield. Read More

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http://doi.wiley.com/10.1002/jlcr.3704
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http://dx.doi.org/10.1002/jlcr.3704DOI Listing
March 2019
3 Reads

Synthesis of [ N ] purine labeled cytokinin glycosides derived from zeatins and topolins with 9-β-d, 7-β-d-glucopyranosyl, or 9-β-d-ribofuranosyl group.

J Labelled Comp Radiopharm 2019 Mar 16;62(3):118-125. Epub 2019 Jan 16.

Department of Organic Chemistry, Faculty of Science, Palacký University, Olomouc, Czech Republic.

Synthesis of [ N ] purine labeled cytokinine glycosides derived from zeatins and topolins containing a 9-β-d, 7-β-d-glucopyranosyl, or 9-β-d-ribofuranosyl group is described. These N -substituted adenine derivatives are intended as internal analytic standards for phytohormone analysis. All labeled compounds were prepared from 6-chloro[ N ]purine (1). Read More

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http://dx.doi.org/10.1002/jlcr.3702DOI Listing
March 2019
2 Reads

Total synthesis of C , N-imidacloprid with three stable isotopes in the pyridine ring.

J Labelled Comp Radiopharm 2019 Mar 16;62(3):126-131. Epub 2019 Jan 16.

Institute for Prevention and Occupational Medicine of the German Social Accident Insurances, Institute of the Ruhr-University Bochum (IPA), Bochum, Germany.

Imidacloprid (IC) is an important crop-protecting insecticide worldwide and commonly used for seed treatment. However, only few data are available on human toxicity of IC. Having in view the metabolic studies at low doses in humans and residue analysis of IC in food and consumer products, we elaborated the synthesis and prepared C , N-IC with three stable isotopes of the "heavy" atoms in positions 1, 2, and 3 of the pyridine ring. Read More

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http://doi.wiley.com/10.1002/jlcr.3703
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http://dx.doi.org/10.1002/jlcr.3703DOI Listing
March 2019
2 Reads

[ F]FPyZIDE: A versatile prosthetic reagent for the fluorine-18 radiolabeling of biologics via copper-catalyzed or strain-promoted alkyne-azide cycloadditions.

J Labelled Comp Radiopharm 2019 Feb 2;62(2):95-108. Epub 2019 Jan 2.

IMIV, Service Hospitalier Frédéric Joliot, CEA, Inserm, Université Paris Sud, CNRS, Université Paris-Saclay, Orsay, France.

Methods for the radiolabeling of biologics with fluorine-18 have been of interest for several decades. A common approach consists in the preparation of a prosthetic reagent, a small molecule bearing a fluorine-18 that is conjugated with the macromolecule to an appropriate function. Click chemistry, and more particularly cycloadditions, is an interesting approach to radiolabel molecules thanks to mild reaction conditions, high yields, low by-products formation, and strong orthogonality. Read More

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http://dx.doi.org/10.1002/jlcr.3701DOI Listing
February 2019
3 Reads

Synthesis of C-labeled ubiquinone and ubiquinol via Pd -mediated rapid C-[ C]methylation using [ C]methyl iodide and 39-demethyl-39-(pinacolboryl)ubiquinone.

J Labelled Comp Radiopharm 2019 Feb 8;62(2):86-94. Epub 2019 Jan 8.

Laboratory for Labeling Chemistry, RIKEN Center for Biosystems Dynamics Research, Kobe, Japan.

To enable positron emission tomography (PET) imaging of the in vivo kinetics of ubiquinone and ubiquinol, which is referred to as coenzyme Q , their C-radiolabeled counterparts were synthesized herein. C-Labeled ubiquinone [ C]-1 was realized by Pd-mediated rapid C-[ C]methylation of [ C]CH I with 39-demethyl-39-(pinacolboryl)ubiquinone, prepared by Ru-catalyzed olefin metathesis of unradiolabeled ubiquinone with 2-(pinacolboryl)propene. Subsequent reduction of [ C]-1 using Na S O yielded C-labeled ubiquinol [ C]-2. Read More

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http://dx.doi.org/10.1002/jlcr.3700DOI Listing
February 2019
6 Reads

Synthesis of C-labelled sulfated N-acetyl-d-lactosamines to aid in the diagnosis of mucopolysaccharidosis diseases.

J Labelled Comp Radiopharm 2019 Feb 11;62(2):67-76. Epub 2018 Dec 11.

Ferrier Research Institute, Victoria University of Wellington, Lower Hutt, New Zealand.

Morquio A syndrome is an autosomal mucopolysaccharide storage disorder that leads to accumulation of keratan sulfate. Diagnosis of this disease can be aided by measuring the levels of keratan sulfate in the urine. This requires the liquid chromatography tandem mass spectrometry (LCMS/MS) measurement of sulfated N-acetyl-d-lactosamines in the urine after cleavage of the keratan sulfate with keratanase II. Read More

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http://dx.doi.org/10.1002/jlcr.3697DOI Listing
February 2019
2 Reads

A versatile synthetic route to the preparation of N heterocycles.

J Labelled Comp Radiopharm 2018 Dec 11. Epub 2018 Dec 11.

International Tomography Center SB RAS, Novosibirsk, Russia.

A robust medium-scale (approximately 3 g) synthetic method for N labeling of pyridine ( N-Py) is reported based on the Zincke reaction. N enrichment in excess of 81% was achieved with approximately 33% yield. N-Py serves as a standard substrate in a wide range of studies employing a hyperpolarization technique for efficient polarization transfer from parahydrogen to heteronuclei; this technique, called SABRE (signal amplification by reversible exchange), employs a simultaneous chemical exchange of parahydrogen and a to-be-hyperpolarized substrate (e. Read More

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http://doi.wiley.com/10.1002/jlcr.3699
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http://dx.doi.org/10.1002/jlcr.3699DOI Listing
December 2018
16 Reads

Synthesis of highly potent lymphocyte function-associated antigen-1 antagonists labeled with carbon-14 and with stable isotopes, part 3.

J Labelled Comp Radiopharm 2019 Feb 12;62(2):77-85. Epub 2018 Dec 12.

Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc, Ridgefield, CT, USA.

The drug candidates (2) and (3) are highly potent LFA-1 inhibitors. They were efficiently prepared labeled with carbon-14 using a palladium-catalyzed carboxylation of an iodo-precursor (5) and sodium formate- C to afford acid [ C]-(6), which was coupled via an amide bond to chiral amines (7) and (8) in 52% and 48% overall yield, respectively, and with specific activities higher than 56 mCi/mmol and radiochemical purities of 99%. For stable isotopes synthesis, the amine [ H ]-(7) was synthesized in three steps from 2-cyanopyridine- H using Kulinkovich-Szymonik aminocyclopropanation, followed by coupling to L-alanine-2,3,3,3- H -N-t-BOC, and then removal of the BOC-protecting group. Read More

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http://dx.doi.org/10.1002/jlcr.3698DOI Listing
February 2019
18 Reads

An efficient method for synthesizing dimethylsulfonio- S-propionate hydrochloride from S.

J Labelled Comp Radiopharm 2019 Jan 12;62(1):52-58. Epub 2018 Dec 12.

Department of Microbiology, University of Georgia, Athens, Georgia, USA.

Dimethylsulfoniopropionate (DMSP, (2-carboxyethyl)dimethylsulfonium) is a highly abundant compound in marine environments. As a precursor to the climatically active gas, dimethylsulfide (DMS), DMSP connects the marine and terrestrial sulfur cycles. However, the fate of DMSP in microbial biomass is not well understood as only a few studies have performed isotopic labeling experiments. Read More

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http://doi.wiley.com/10.1002/jlcr.3696
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http://dx.doi.org/10.1002/jlcr.3696DOI Listing
January 2019
18 Reads

Radiolabeling, quality control, biodistribution, and imaging studies of Lu-ibandronate.

J Labelled Comp Radiopharm 2019 Jan 28;62(1):43-51. Epub 2018 Nov 28.

Department of Nuclear Medicine, Affiliated Hospital of Southwest Medical University, Luzhou, China.

The purposes of this study were as follows: (1) to radiolabel ibandronic acid (IBA, a third-generation bisphosphonate) with Lu, investigating optimal labeling conditions, and (2) to analyze biodistribution and imaging properties of intravenous Lu-ibandronate ( Lu-IBA) administered in animals. Lu-labeled methylene diphosphonate ( Lu-MDP) served as a comparator agent. Differing proportions of IBA solution and LuCl solution were combined to determine an optimal ratio for radiolabeling purposes, varying pH, temperature, and time to establish ideal reactivity conditions. Read More

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http://doi.wiley.com/10.1002/jlcr.3694
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http://dx.doi.org/10.1002/jlcr.3694DOI Listing
January 2019
23 Reads

A simplified radiosynthesis of [ F]MK-6240 for tau PET imaging.

J Labelled Comp Radiopharm 2019 Feb 19;62(2):109-114. Epub 2018 Dec 19.

Montreal Neurological Institute, McGill University, Montreal, Quebec, Canada.

[ F]MK-6240 (6-(fluoro)-3-(1H-pyrrolo[2,3-c]pyridin-1-yl)isoquinolin-5-amine) is a highly selective PET radiotracer for the in vivo imaging of neurofibrillary tangles (NFTs). [ F]MK-6240 was synthesized in one step from its bis-Boc protected precursor N-[(tert-butoxy)carbonyl]-N-(6-nitro-3-[1H-pyrrolo[2,3-c]pyridin-1-yl]isoquinolin-5-yl) carbamate in DMSO using [ F] fluoride with TEA HCO with step-wise heating up to 150°C, resulting in an isolated radiochemical yield of 9.8% ± 1. Read More

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http://doi.wiley.com/10.1002/jlcr.3695
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http://dx.doi.org/10.1002/jlcr.3695DOI Listing
February 2019
32 Reads

Evaluation of [ F]2FP3 in pigs and non-human primates.

J Labelled Comp Radiopharm 2019 Jan 6;62(1):34-42. Epub 2018 Dec 6.

Neurobiology Research Unit and Center for Integrated Molecular Brain Imaging, Copenhagen University Hospital, Rigshospitalet, Copenhagen, Denmark.

So far, no suitable 5-HT R radioligand exists for clinical positron emission tomography (PET) imaging. [ F]2FP3 was first tested in vivo in cats, and the results were promising for further evaluations. Here, we evaluate the radioligand in pigs and non-human primates (NHPs). Read More

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http://doi.wiley.com/10.1002/jlcr.3692
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http://dx.doi.org/10.1002/jlcr.3692DOI Listing
January 2019
13 Reads

Synthesis and characterization of C-labeled benzyl amidine derivatives as PET radioligands for GluN2B subunit of the NMDA receptors.

J Labelled Comp Radiopharm 2018 Dec 18;61(14):1095-1105. Epub 2018 Nov 18.

Department of Biophysical Chemistry, Kobe Pharmaceutical University, Kobe, Japan.

GluN2B-containing NMDA receptors (NMDARs) play fundamental roles in learning and memory, although they are also associated with various brain disorders. In this study, we synthesized and evaluated three C-labeled N-benzyl amidine derivatives 2-[ C]methoxybenzyl) cinnamamidine ([ C]CBA), N-(2-[ C]methoxybenzyl)-2-naphthamidine ([ C]NBA), and N-(2-[ C]methoxybenzyl)quinoline-3-carboxamidine ([ C]QBA) as PET radioligands for these receptors. The C-benzyl amidines were synthesized via conventional methylation of corresponding des-methyl precursors with [ C]CH I. Read More

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http://doi.wiley.com/10.1002/jlcr.3691
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http://dx.doi.org/10.1002/jlcr.3691DOI Listing
December 2018
7 Reads

Jörg Steinbach-A highly motivated radiopharmaceutical scientist.

J Labelled Comp Radiopharm 2018 Oct 29. Epub 2018 Oct 29.

Emeritus, Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology (ETH), Zürich, Switzerland.

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http://dx.doi.org/10.1002/jlcr.3689DOI Listing
October 2018
4 Reads

Identification of unexpected unlabeled N,N-dimethylamide formation in the synthesis of deuterated fragment of ribociclib by a HATU-mediated coupling reaction.

J Labelled Comp Radiopharm 2019 Feb 22;62(2):62-66. Epub 2018 Nov 22.

Jiangsu Key Laboratory of Targeted Antiviral Research, Chia Tai Tianqing Pharmaceutical Group Co., LTD, Nanjing, China.

Starting from N,N-dimethylamine and D O, deuterated fragment of ribociclib was synthesized for use as a mass spectroscopy internal standard. Furthermore, systematic studies on D (unlabeled material) formation during the amidation reaction were performed, leading to the identification of a coupling reagent, HATU (O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate), as main cause. Finally, an alternative route was designed using EDCI/HOBT as coupling reagents to produce the desired deuterated compound without D residue. Read More

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http://doi.wiley.com/10.1002/jlcr.3690
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http://dx.doi.org/10.1002/jlcr.3690DOI Listing
February 2019
6 Reads

Radiosynthesis of O-(1-[ F]fluoropropan-2-yl)-O-(4-nitrophenyl)methylphosphonate: A novel PET tracer surrogate of sarin.

J Labelled Comp Radiopharm 2018 Dec 4;61(14):1089-1094. Epub 2018 Nov 4.

Department of Radiology and Biomedical Imaging, University of California, San Francisco, San Francisco, CA, USA.

O-(1-Fluoropropan-2-yl)-O-(4-nitrophenyl) methylphosphonate is a reactive organophosphate ester (OP) developed as a surrogate of the chemical warfare agent sarin that forms a similar covalent adduct at the active site serine of acetylcholinesterase. The radiolabeled O-(1-[ F]fluoropropan-2-yl)-O-(4-nitrophenyl) methylphosphonate ([ F] fluorosarin surrogate) has not been previously prepared. In this paper, we report the first radiosynthesis of this tracer from the reaction of bis-(4-nitrophenyl) methylphosphonate with 1-[ F]fluoro-2-propanol in the presence of DBU. Read More

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http://doi.wiley.com/10.1002/jlcr.3688
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http://dx.doi.org/10.1002/jlcr.3688DOI Listing
December 2018
12 Reads

Radiosynthesis of an F-fluoroglycosylated aminoferrocene for in-vivo imaging of reactive oxygen species activity by PET.

J Labelled Comp Radiopharm 2018 Dec 18;61(14):1081-1088. Epub 2018 Oct 18.

Department of Nuclear Medicine, Molecular Imaging and Radiochemistry, Friedrich-Alexander University Erlangen-Nürnberg (FAU), Erlangen, Germany.

The imaging of reactive oxygen species (ROS) at the molecular level with high sensitivity and specificity by positron emission tomography (PET) could be of enormous interest to increase our knowledge about ROS activity and signalling, especially in tumours. The aim of this research was to optimise the click chemistry-based radiosynthesis of an F-labelled aminoferrocene glycoconjugate that was derived from an N-alkylaminoferrocene lead structure known to have anticancer activity in vitro. Applying the solvent system phosphate buffer/THF (12/5), Cu(OAc) and sodium ascorbate as reducing agent at 60°C, the alkyne 1 reacted with the F-labelled glycosyl azide [ F]2 in the presence of carrier 3 (47μM) to obtain carrier-added [ F]4 in a radiochemical yield of 85%. Read More

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http://doi.wiley.com/10.1002/jlcr.3687
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http://dx.doi.org/10.1002/jlcr.3687DOI Listing
December 2018
8 Reads

Improved, one-pot synthesis of 6-[ F]fluorodopamine and quality control testing for use in patients with neuroblastoma.

J Labelled Comp Radiopharm 2018 Dec 22;61(14):1069-1080. Epub 2018 Oct 22.

Division of Nuclear Medicine, Department of Diagnostic Imaging, St. Jude Children's Research Hospital, Memphis, Tennessee, USA.

6-[ F]Fluorodopamine ([ F]F-DA) is taken into cells via the norepinephrine transporter (NET). Recent [ F]F-DA positron emission tomography-computed tomography (PET-CT) imaging of adult neuroendocrine tumors shows a dramatic improvement in sensitivity over the standard-of-care, meta-iodobenzylguanidine (MIBG) single-photon emission computed tomography (SPECT)-CT. A new precursor (ALPdopamine™) allows no-carrier-added synthesis resulting in high-molar activity [ F]F-DA. Read More

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http://doi.wiley.com/10.1002/jlcr.3685
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http://dx.doi.org/10.1002/jlcr.3685DOI Listing
December 2018
10 Reads

A [ C] CO dispensing system for rapid screening of carbonylation reactions.

J Labelled Comp Radiopharm 2018 Dec 25;61(14):1110-1114. Epub 2018 Oct 25.

Molecular Imaging Program at Stanford (MIPS), Department of Radiology, Stanford University, School of Medicine, Stanford, California, USA.

[ C] CO is a highly versatile synthon that allows for labeling at carbonyl positions of many molecules by means of transition metal-mediated carbonylation reactions. The intrinsic complexity of carbonylation reactions often requires tedious screening of reaction conditions for obtaining satisfying yields. Herein, a [ C] CO dispending system for performing multiple reactions with a single batch of cyclotron-produced [ C]CO is described. Read More

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http://dx.doi.org/10.1002/jlcr.3686DOI Listing
December 2018
2 Reads

New trends and methods for carbon isotope chemistry.

J Labelled Comp Radiopharm 2018 Nov 29;61(13):920-921. Epub 2018 Oct 29.

Integrated Drug Discovery, Isotope Chemistry, Sanofi, Frankfurt, Germany.

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http://dx.doi.org/10.1002/jlcr.3684DOI Listing
November 2018
11 Reads

Radioiodination and biological distribution of a new s-triazine derivative for tumor uptake evaluation.

J Labelled Comp Radiopharm 2018 Dec 9;61(14):1058-1068. Epub 2018 Oct 9.

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Helwan University, Cairo, Egypt.

A newly synthesized s-triazine derivative 1,1',1″-(((1,3,5-triazine-2,4,6-triyl) tris (azanediyl)) tris (benzene-4,1-diyl))tris (ethan-1-one), (1), was synthesized as a part of an ongoing research for development of novel s-triazine-based radiopharmaceuticals. In-vitro cell viability assay against different human cancer cell lines showed very promising inhibitory activity of the synthesized compound. This finding encouraged the radioiodination of 1 to study the degree of its localization in tumor site for evaluating the possibility of its use as a tumor imaging agent. Read More

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http://dx.doi.org/10.1002/jlcr.3682DOI Listing
December 2018
4 Reads

Synthesis and biodistribution studies of Tc labeled fatty acid derivatives prepared via "Click approach" for potential use in cardiac imaging.

J Labelled Comp Radiopharm 2018 Dec 30;61(14):1048-1057. Epub 2018 Sep 30.

Homi Bhabha National Institute (HBNI), Mumbai, India.

I-Iodophenylpentadecanoic acid (IPPA) is a metabolic agent used in nuclear medicine for diagnosis of myocardial defects. Efforts are underway worldwide to develop a Tc substitute of the above radiopharmaceutical for the aforementioned application. Herein, we report synthesis and biodistribution studies of Tc labeled fatty acids (8, 11, and 15 carbons) obtained via "click chemistry" for its potential use in myocardial imaging. Read More

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http://dx.doi.org/10.1002/jlcr.3681DOI Listing
December 2018
4 Reads
1.190 Impact Factor

New radical methods for the potential synthesis of carbon-13 and carbon-14 labeled complex products.

Authors:
Brad D Maxwell

J Labelled Comp Radiopharm 2018 Dec 11;61(14):1024-1035. Epub 2018 Oct 11.

Vertex Pharmaceuticals Incorporated, Boston, MA, USA.

The isotopic labeling of molecules for agrichemical and pharmaceutical uses is becoming more challenging as molecules become larger, involve more stereochemistry, and as intellectual property rights become more complex. As such, isotope chemists need to continually add new isotopic methods to their armamentarium to successfully label complex molecules with carbon-13 and carbon-14. Recently, there has been a surge in the use of radicals to form new carbon-carbon bonds and for the incorporation of functional groups which can be used to incorporate isotopically labeled carbons. Read More

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http://doi.wiley.com/10.1002/jlcr.3680
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http://dx.doi.org/10.1002/jlcr.3680DOI Listing
December 2018
5 Reads

Synthesis of deuterium-labeled 2-quinoxalinecarboxylic acid and 3-methylquinoxaline-2-carboxylic acid from deuterium aniline.

J Labelled Comp Radiopharm 2018 Dec 2;61(14):1043-1047. Epub 2018 Sep 2.

Animal and Plant and Food Inspection and Quarantine Technical Center, Shanghai Exit and Entry Inspection and Quarantine Bureau, Shanghai, China.

An efficient and simple synthetic route of deuterium-labeled 2-quinoxalinecarboxylic acid-d (QCA-d ) and 3-methylquinoxaline-2-carboxylic acid-d (MQCA-d ) is presented with 99.9% and 99.6% isotopic enrichment using aniline-d as labeled starting material. Read More

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http://dx.doi.org/10.1002/jlcr.3679DOI Listing
December 2018
3 Reads