Biomedizinische Forschungsreagenzien GmbH

Radeberg, Germany

Biomedizinische Forschungsreagenzien GmbH

Radeberg, Germany

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Schoultz B.W.,University of Oslo | Hjornevik T.,University of Oslo | Reed B.J.,University of Oslo | Marton J.,Biomedizinische Forschungsreagenzien GmbH | And 5 more authors.
Journal of Medicinal Chemistry | Year: 2014

We report the synthesis and biological evaluation of a triplet of 6-O- 18F-fluoroethylated derivatives of structurally related orvinols that span across the full range of intrinsic activities, the antagonist diprenorphine, the partial agonist buprenorphine, and the full agonist phenethyl-orvinol. [18F]fluoroethyl-diprenorphine, [ 18F]fluoroethyl-buprenorphine, and [18F]fluoroethyl- phenethyl-orvinol were prepared in high yields and quality from their 6-O-desmethyl-precursors. The results indicate suitable properties of the three 6-O-18F-fluoroethylated derivatives as functional analogues to the native carbon-11 labeled versions with similar pharmacological properties. © 2014 American Chemical Society.


Riss P.J.,University of Cambridge | Hong Y.T.,University of Cambridge | Marton J.,Biomedizinische Forschungsreagenzien GmbH | Caprioli D.,University of Cambridge | And 8 more authors.
Journal of Nuclear Medicine | Year: 2013

We have investigated the opioid receptor (OR) agonist (20R)-4,5-α- epoxy-6-(2-18F-fluoroethoxy)-3-hydroxy-α,17-dimethyl-α- (2- phenyleth-1-yl)-6,14-ethenomorphinan-7-methanol (18F-FE-PEO) as a candidate OR PET ligand. This tracer is attractive because it combines 18F labeling, is suited to the slow kinetics of high-affinity ligands, and has agonist binding, which has been shown to be more sensitive to changes in OR occupation than is antagonist binding. Methods: Agonist potency and off-target binding were investigated in vitro, and autoradiographic studies on rat brain sections were used to assess binding patterns. Quantification of the tracer in vivo was investigated using small-animal PET in rats with blood sampling. Results: 18F-FE-PEO was obtained by direct nucleophilic radiofluorination and subsequent deprotection with a yield of 28% ± 15%, a specific activity of 52-224 MBq/nmol, and a radiochemical purity of more than 97% (90 min from end of bombardment). In vitro studies showed it to be a full agonist ligand, which selectively binds to OR with high affinity, although it is not selective to a single OR subtype (inhibition constant, 0.4-1.6 nM across OR subtypes). Autoradiography binding patterns were consistent with the known distribution of OR, although nondisplaceable signal typically constituted one third of the signal in OR-dense regions. Although metabolites were present in blood (~40% of plasma radioactivity was nonparent 3 h after injection), no significant metabolite fraction was found in brain tissue, aiding PET quantification. A plasma input 2-tissue-compartment model provided good fits to the PET data, and regional distribution volumes from the latter correlated well with those from Logan plot analysis (r2 = 0.98). The cerebellum had the lowest distribution volume, but the time-activity curve data could not be adequately fitted with a 1-tissue-compartment model. Reference tissue models using the cerebellum as the reference region did not provide good fits to the data, so blood-based kinetic analysis is recommended. Conclusion: As the first 18F-labeled OR agonist ligand, 18FFE- PEO is a useful addition to the existing OR ligand portfolio. Copyright © 2013 by the Society of Nuclear Medicine and Molecular Imaging, Inc.


Marton J.,Biomedizinische Forschungsreagenzien GmbH | Glaenzel B.,Biomedizinische Forschungsreagenzien GmbH | Roessler J.,Biomedizinische Forschungsreagenzien GmbH | Roessler J.,TU Dresden | And 3 more authors.
Molecules | Year: 2012

The route selection and development of a convenient synthesis of 4-carboxy-4-anilidopiperidines is described. Previous routes were hampered by the low yield of the target esters as well as the inability to convert the esters to the required free acids. Considerations for large-scale production led to a modified synthesis that utilised a tert-butyl ester of 4-carboxy-4-anilidopiperidines which resulted in a dramatic increase in the overall yield of the target N-propionylated-4-anilidopiperidine-4-carboxylic acids and their corresponding methyl esters. These compounds are now available for use as precursors and reference standards, of particular value for the production of 11C and 18F-labelled 4-carboxy-4- anilidopiperidine radiotracers. © 2012 by the authors.


PubMed | Biomedizinische Forschungsreagenzien GmbH
Type: Journal Article | Journal: Molecules (Basel, Switzerland) | Year: 2012

The route selection and development of a convenient synthesis of 4-carboxy-4-anilidopiperidines is described. Previous routes were hampered by the low yield of the target esters as well as the inability to convert the esters to the required free acids. Considerations for large-scale production led to a modified synthesis that utilised a tert-butyl ester of 4-carboxy-4-anilidopiperidines which resulted in a dramatic increase in the overall yield of the target N-propionylated- 4-anilidopiperidine-4-carboxylic acids and their corresponding methyl esters. These compounds are now available for use as precursors and reference standards, of particular value for the production of 11C and 18F-labelled 4-carboxy-4-anilidopiperidine radiotracers.

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