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


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

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

Dept. of Nuclear Medicine, Medical University 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

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

J Labelled Comp Radiopharm 2019 Jan 28. Epub 2019 Jan 28.

Wolfson Brain Imaging Centre, Department of Clinical Neurosciences, University of Cambridge, Addenbrooke's Hospital, Cambridge, United Kingdom.

[ 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
January 2019
1 Read
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 Jan 22. Epub 2019 Jan 22.

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

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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
January 2019
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New Tc-(CO) -radiolabeld arylpiperazine pharmacophore as potent 5-HT serotonin receptor radiotracer: Docking studies, chemical synthesis, radiolabeling and biological evaluation.

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

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-carbons linker and radio-labeled 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
January 2019

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

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

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
January 2019
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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 Jan 20. Epub 2019 Jan 20.

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

Objective: 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.

Methods: 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
January 2019
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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
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An azeotropic drying-free approach for copper-mediated radiofluorination without addition of base.

J Labelled Comp Radiopharm 2019 Jan 15. Epub 2019 Jan 15.

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

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
January 2019

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

J Labelled Comp Radiopharm 2019 Jan 2. Epub 2019 Jan 2.

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
January 2019
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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 2018 Dec 28. Epub 2018 Dec 28.

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
December 2018

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

J Labelled Comp Radiopharm 2018 Dec 27. Epub 2018 Dec 27.

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
December 2018
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[ 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 2018 Dec 17. Epub 2018 Dec 17.

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
December 2018
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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 2018 Dec 16. Epub 2018 Dec 16.

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
December 2018
1 Read

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

J Labelled Comp Radiopharm 2018 Nov 22. Epub 2018 Nov 22.

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
November 2018

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

J Labelled Comp Radiopharm 2018 Nov 22. Epub 2018 Nov 22.

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
November 2018
9 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
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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
15 Reads

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

J Labelled Comp Radiopharm 2018 Nov 13. Epub 2018 Nov 13.

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
November 2018
25 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
3 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
4 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
1 Read

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 2018 Oct 29. Epub 2018 Oct 29.

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

Starting from N,N-dimethylamine and D O, deuterated fragment of ribociclib was synthesized for use as an mass spectroscopy (MS) 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
October 2018
5 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
7 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
2 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
2 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

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
1 Read

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
2 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
2 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
2 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
2 Reads

Synthesis of deuterium-labeled crizotinib, a potent and selective dual inhibitor of mesenchymal-epithelial transition factor (c-MET) kinase and anaplastic lymphoma kinase (ALK).

J Labelled Comp Radiopharm 2018 Dec 9;61(14):1036-1042. Epub 2018 Sep 9.

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

To more accurately and rapidly achieve quantitative detection of clinical crizotinib samples, stable isotope labeled crizotinib was required as an internal standard. We have developed a method to prepare racemic [D ] crizotinib using a base-catalyzed H/D exchange of both nitroso compound 2 and the acetophenone compound 6 with D O and NaBD reduction of 7 as the key steps to introduce the 9 deuterium atoms. Starting with 4-hydroxypiperidine, 14-step synthesis furnished the desired racemic [D ] crizotinib 18. Read More

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http://dx.doi.org/10.1002/jlcr.3678DOI Listing
December 2018
2 Reads
1.190 Impact Factor

Preparation of a radiolabeled GnRH-I analogue derivative with In as a new anti-proliferative agent.

J Labelled Comp Radiopharm 2018 Oct 4;61(12):903-911. Epub 2018 Sep 4.

Radiation Application Research School, Nuclear Science and Technology Research Institute (NSTRI), Tehran, Iran.

The new GnRH-Ιanalogue developed in this paper was based on the D-Trp -GnRH-Ι-scaffold, and its potency was increased by the replacement Gly-NH by NH-NH binding to the Gly at position 10. Triptorelin-Hydrazide analogue was synthesized using solid phase. For In labeling, synthesized peptide was followed by conjugation with DOTA using pSCN-Bn-DOTA. Read More

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http://doi.wiley.com/10.1002/jlcr.3677
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http://dx.doi.org/10.1002/jlcr.3677DOI Listing
October 2018
16 Reads

Tritiation of azido-labeled diiodo cabazitaxel (Jevtana) and docetaxel (Taxotere) derivatives to generate H-photoaffinity probes.

J Labelled Comp Radiopharm 2018 Oct 30;61(12):895-902. Epub 2018 Aug 30.

SANOFI R&D, Integrated Drug Discovery, Sanofi-Aventis Deutschland GmbH, Frankfurt am Main, Germany.

Radiolabelled azidophenyl analogues can make powerful photoaffinity probes for the identification of molecular targets. We describe our efforts to prepare tritiated azidophenyl analogues of the taxols cabazitaxel and docetaxel. Late-stage tritiation by isotope exchange with diiodo precursors resulted in reduction of the azide moiety, which could only be overcome by addition of high excess of a sacrificial azide. Read More

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http://dx.doi.org/10.1002/jlcr.3675DOI Listing
October 2018
2 Reads

Radiosynthesis and validation of [Carboxy- C]4-Aminobenzoic acid ([ C]PABA), a PET radiotracer for imaging bacterial infections.

J Labelled Comp Radiopharm 2019 Jan 29;62(1):28-33. Epub 2018 Aug 29.

Division of Nuclear Medicine and Molecular Imaging, Department of Radiology, Baltimore, Maryland, USA.

In this practitioner protocol, the radiochemical synthesis of [ C] PABA is described in detail, and a quality control summary of three validation productions is presented. The results indicate that the radiotracer product can be produced in good radiochemical yield (14% at end-of-synthesis (EOS)) at high specific activity (molar activity 11 Ci/μmole EOS; 407 GBq/μmole) and high chemical and radiochemical purity as a sterile, pyrogen-free solution suitable for injection conforming to current Good Manufacturing Practice (cGMP) requirements. Read More

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http://dx.doi.org/10.1002/jlcr.3674DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6338486PMC
January 2019
18 Reads

Development of single vial kits for preparation of Ga-labelled hexavalent lactoside for PET imaging of asialoglycoprotein receptor.

J Labelled Comp Radiopharm 2018 Oct 3;61(12):885-894. Epub 2018 Sep 3.

Isotope Application Division, Institute of Nuclear Energy Research, Taoyuan City, Taiwan (ROC).

The aim of this study was to formulate and evaluate the freeze-dried kit of NOTA-hexavalent lactoside (NOTA-HL) for the preparation of Ga-labeled glycoligand for PET imaging of the asialoglycoprotein receptor (ASGPR). GaCl was obtained from a commercial Ge/ Ga generator. Single-vial kits of HL were formulated. Read More

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http://dx.doi.org/10.1002/jlcr.3673DOI Listing
October 2018
19 Reads
1.190 Impact Factor

Two new convenient syntheses of 14C-squalene from turbinaric acid.

J Labelled Comp Radiopharm 2018 Oct 10;61(12):878-884. Epub 2018 Sep 10.

Isotope Chemistry, Integrated Drug Discovery, Sanofi-Aventis R&D, Vitry-sur-Seine, France.

Carbon-14 labeled (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene, also known as squalene, was synthesized as a tool for pharmacokinetic studies. Two simple and efficient labeling approaches were developed to give [2- C]-squalene and [3- C]-squalene from a halogenated precursor derived from turbinaric acid. They were obtained in 13. Read More

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http://dx.doi.org/10.1002/jlcr.3672DOI Listing
October 2018
11 Reads

An efficient synthesis of trace amine-associated receptor agonist [1- C]tyramine.

J Labelled Comp Radiopharm 2019 Jan 31;62(1):24-27. Epub 2018 Jul 31.

Custom Synthesis, PerkinElmer Health Sciences Inc., Waltham, MA, USA.

The 2-step synthesis of [1- C]tyramine hydrochloride is described with the product being characterized by TLC, HPLC, and UV spectroscopy. Several methods are provided to purify [1- C]tyramine hydrochloride, and its storage and stability are also discussed. Read More

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http://dx.doi.org/10.1002/jlcr.3671DOI Listing
January 2019
2 Reads

Synthesis of carbon-14 labeled ketamine and norketamine.

J Labelled Comp Radiopharm 2018 Sep 29;61(11):864-868. Epub 2018 Jul 29.

Isotope Chemistry and Biotransformations, Janssen Research & Development, Johnson & Johnson, Spring House, Pennsylvania.

Ketamine is a well-known general anesthetic that inhibits cerebral NMDA receptors. Norketamine is a major circulating metabolite of this drug. A nasal spray formulation of esketamine, the S enantiomer of ketamine, is under development for the management of treatment-resistant depression. Read More

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http://dx.doi.org/10.1002/jlcr.3669DOI Listing
September 2018
7 Reads

Indium-111 labeling of high-density lipoprotein-mimicking phospholipid-styrene maleic acid copolymer complexes and its biodistribution in mice.

J Labelled Comp Radiopharm 2018 Sep 20;61(11):857-863. Epub 2018 Jul 20.

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

Discoidal lipid nanoparticles mimicking native high-density lipoproteins (HDL) are promising delivery vehicles of drugs and/or imaging agents. However, little is known about the in vivo biodistribution of such discoidal lipid nanoparticles compared to liposomes, clinically available spherical lipid nanoparticles. Recently, it has been reported that synthetic polymers instead of apolipoproteins can be complexed with phospholipid to form discoidal nanoparticles. Read More

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http://doi.wiley.com/10.1002/jlcr.3668
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http://dx.doi.org/10.1002/jlcr.3668DOI Listing
September 2018
6 Reads

Recent developments in heterocycle labeling with carbon isotopes.

J Labelled Comp Radiopharm 2018 Nov 13;61(13):988-1007. Epub 2018 Jul 13.

CEA-Saclay, JOLIOT, Service de Chimie Bioorganique et de Marquage, Gif sur Yvette, France.

Heterocycles play an essential role in modern pharmaceutical and agrochemical developments, representing a very common structural unit in marketed drugs. Over the 46 new drugs approved in 2017 by the FDA, 25 contain in their structure a heterocyclic core. The development of novel and straightforward labeling strategies for the effective insertion of carbon isotopes into heterocylic scaffolds is an inspiring and vibrant field of research. Read More

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http://dx.doi.org/10.1002/jlcr.3666DOI Listing
November 2018
7 Reads

Synthesis, bioconjugation and stability studies of [ F]ethenesulfonyl fluoride.

J Labelled Comp Radiopharm 2018 Sep 12;61(11):847-856. Epub 2018 Jul 12.

Australian Nuclear Science and Technology Organisation (ANSTO), Lucas Heights, New South Wales, Australia.

Fluorine-18 labelled prosthetic groups (PGs) are often necessary for radiolabelling sensitive biological molecules such as peptides and proteins. Several shortcomings, however, often diminish the final yield of radiotracer. In an attempt to provide higher yielding and operationally efficient tools for radiolabelling biological molecules, we describe herein the first radiochemical synthesis of [ F]ethenesulfonyl fluoride ([ F]ESF) and its Michael conjugation with amino acids and proteins. Read More

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http://dx.doi.org/10.1002/jlcr.3667DOI Listing
September 2018
18 Reads

Radioimmunoimaging and targeting treatment in an immunocompetent murine model of triple-negative breast cancer using radiolabeled anti-programmed death-ligand 1 monoclonal antibody.

J Labelled Comp Radiopharm 2018 Sep 4;61(11):826-836. Epub 2018 Jul 4.

Department of Nuclear Medicine, Peking University First Hospital, Beijing, China.

The overall aim of this study was to evaluate whether iodine-131 radiolabeled monoclonal antibody (mAb) targeting programmed death-ligand 1 (PD-L1) can be used for imaging of PD-L1 expression noninvasively in vivo and playing synergistic effect combined with immunotherapy. Anti-PD-L1 mAb was radiolabeled with iodine-131 ( I-PD-L1 mAb) and was characterized in vitro. Biodistribution and imaging in vivo were performed periodically. Read More

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http://doi.wiley.com/10.1002/jlcr.3650
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http://dx.doi.org/10.1002/jlcr.3650DOI Listing
September 2018
9 Reads

Lu-DOTMP induces G2/M cell cycle arrest and apoptosis in MG63 cell line.

J Labelled Comp Radiopharm 2018 Sep 11;61(11):837-846. Epub 2018 Jul 11.

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

Bone pain is the major manifestation of skeletal metastases. Although various treatment modalities are available for bone pain palliation, use of radiolabeled phosphonates is documented to be more effective. Among radionuclides available for this purpose, lutetium-177 is gaining popularity due to its moderate beta energy, theranostic capability, favorable half-life and convenient production logistics. Read More

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http://doi.wiley.com/10.1002/jlcr.3651
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http://dx.doi.org/10.1002/jlcr.3651DOI Listing
September 2018
3 Reads
1.190 Impact Factor

Automated GMP-production of α-[ C]methyl-L-tryptophan using a tracer production system (TPS).

J Labelled Comp Radiopharm 2018 Dec 26;61(14):1106-1109. Epub 2018 Jun 26.

Department of Medicinal Chemistry, Uppsala University, Uppsala, Sweden.

The radiosynthesis and GMP validation of [ C]AMT for human use are described. Three consecutive batches were produced giving 940-3790 MBq (4%-17% RCY, decay corrected, based on [ C]CO ) of the tracer. The molar activity at the end of synthesis was 19 to 35 GBq/μmol, the radiochemical purity was ≥98%, and the enantiomeric purity was >99%. Read More

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http://dx.doi.org/10.1002/jlcr.3648DOI Listing
December 2018
3 Reads
1.190 Impact Factor

Synthesis of C-labeled 5-aminoimidazole-4-carboxamide-1-β-D-[ C ] ribofuranosyl 5'-monophosphate.

J Labelled Comp Radiopharm 2018 Sep 15;61(11):820-825. Epub 2018 Jul 15.

Center for Drug Discovery, RTI International, NC, United States.

5-Aminoimidazole-4-carboxamide-1-β-D-[ C ] ribofuranosyl 5'-monophosphate ([ C ribose] AICAR-PO H ) (6) has been synthesized from [ C ]adenosine. Incorporation of the mass-label into [ C ribose] AICAR-PO H provides a useful standard to aid in metabolite identification and quantification in monitoring metabolic pathways. A synthetic route to the C-labeled compound has not been previously reported. Read More

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http://dx.doi.org/10.1002/jlcr.3647DOI Listing
September 2018
7 Reads

Synthesis of carbon-14 labeled ZJ0712, a novel strobilurin fungicide.

J Labelled Comp Radiopharm 2018 Sep 6;61(11):812-819. Epub 2018 Jul 6.

Institute of Nuclear-Agricultural Science, Zhejiang University, Hangzhou, China.

ZJ0712, a broad-spectrum fungicidal ingredient of strobilurin, exhibits a high protective and curative activity against plant pathogenic fungi. To support the study on its metabolism, residue, environmental behavior, and fate for safety evaluation, two versions of carbon-14 labeled ZJ0712, methyl (E)-2-(2-((2,5-dimethylphenoxy)methyl)phenyl)-3-methoxy[2- C]acrylate (2) and methyl (E)-2-(2-((2,5-dimethyl[phenyl-U- C ]phenoxy)methyl)phenyl)-3-methoxyacrylate (3), were synthesized from barium [ C]carbonate in 6-step yield of 47% and from 2,5-dimethyl[phenyl-U- C ]phenol in the yield of 91%, respectively. Read More

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http://dx.doi.org/10.1002/jlcr.3646DOI Listing
September 2018
10 Reads

Recent developments in carbonylation chemistry using [ C]CO, [ C]CO, and [ C]CO.

J Labelled Comp Radiopharm 2018 Nov 28;61(13):949-987. Epub 2018 Jun 28.

Carbon Dioxide Activation Center (CADIAC), Interdisciplinary Nanoscience Center (iNANO), Department of Chemistry, Aarhus University, Aarhus C, Denmark.

Carbon monoxide represents the most important C1-building block for the chemical industry, both for the production of bulk and fine chemicals, but also for synthetic fuels. Yet its toxicity and subsequently its cautious handling have limited its applications in medicinal chemistry research and in particular for the synthesis of pharmaceutically relevant molecules. Recent years have nevertheless witnessed a considerable headway on the development of carbon monoxide surrogates and reactor systems, which provide an ideal setting for performing carbonylation chemistry with stoichiometric and substoichiometric carbon monoxide. Read More

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http://dx.doi.org/10.1002/jlcr.3645DOI Listing
November 2018
5 Reads

Synthesis of obeticholic acid, a farnesoid X receptor agonist, and its major metabolites labeled with deuterium.

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

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

Simple and facile methods for the synthesis of deuterium-labeled obeticholic acid and its 2 metabolites, glycine and taurine conjugates of obeticholic acid, are described herein. The 3 deuterated compounds were applicable for use as internal standards in drug development. Read More

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http://dx.doi.org/10.1002/jlcr.3643DOI Listing
May 2018
3 Reads