Synthesis and evaluation of 5, 7-dichloro-4-(3-$$4-[4-(2-[18F] fluoroethyl)-piperazin-1-yl]-phenyl$$-ureido)-1, 2, 3, 4-tetrahydroquinoline-2-carboxylic acid as a potential NMDA ligand to study glutamatergic neurotransmission in vivo

Publikationstyp:
Zeitschriftenaufsatz
Metadaten:
Autoren
  • M Piel
  • R Schirrmacher
  • S Höhnemann
  • W Hamkens
  • B Kohl
  • M Jansen
  • U Schmitt
  • H Lüddens
  • G Dannhardt
  • F Rösch
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000183803700006&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1002/jlcr.682
eISSN
1099-1344
Externe Identifier
  • Clarivate Analytics Document Solution ID: 694YU
ISSN
0362-4803
Ausgabe der Veröffentlichung
7
Zeitschrift
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS
Schlüsselwörter
  • glutamate
  • NMDA receptor
  • glycine binding site
  • F-18-fluoroalkylation
Paginierung
645 - 659
Datum der Veröffentlichung
2003
Status
Published
Titel
Synthesis and evaluation of 5,7-dichloro-4-(3-{4-[4-(2-[<SUP>18</SUP>F]fluoroethyl)-piperazin-1-yl]-phenyl}-ureido)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid as a potential NMDA ligand to study glutamatergic neurotransmission in vivo
Sub types
  • Article
Ausgabe der Zeitschrift
46

Datenquelle: Web of Science (Lite)

Andere Metadatenquellen:
Abstract
<jats:title>Abstract</jats:title><jats:p>The neurotransmitter glutamate is thought to be crucially involved in a huge number of neurological and psychiatric disorders, such as Morbus Parkinson, Alzheimer's disease and schizophrenia. Aiming at an improved diagnostic tool for PET a new [<jats:sup>18</jats:sup>F]fluorine labelled NMDA receptor ligand was developed that may potentially allow the <jats:italic>in vivo</jats:italic> visualization of glutama‐tergic neurotransmission. The <jats:sup>19</jats:sup>F‐analogue <jats:italic>trans</jats:italic>‐5,7‐dichloro‐4‐(3‐{4‐[4‐(2‐fluoroethyl)‐piperazin‐1‐yl]‐phenyl}‐ureido)‐1,2,3,4‐tetrahydro quinoline‐2‐carboxylic acid was synthesised to determine the binding affinity, lipophilicity and biodistribution of the ligand. This substance exhibits a <jats:italic>K</jats:italic><jats:sub><jats:italic>i</jats:italic></jats:sub> of 12 nM for the glycine binding site using [<jats:sup>3</jats:sup>H]MDL‐105,519 assays on pig cortical membranes. A logD of 1.3 was determined for this compound according to the OECD guidelines employing the HPLC method. Radiosynthesis of this ligand was achieved by labelling the precursor <jats:italic>trans</jats:italic>‐5,7‐dichloro‐4‐[3‐(4‐piperazin‐1‐yl‐phenyl)‐ureido]‐1,2,3,4‐tetrahydroquinoline‐2‐carboxylic acid methyl ester with 2‐[<jats:sup>18</jats:sup>F]fluoroethyltosylate and subsequent cleaving of the methyl ester moiety, resulting in an overall decay corrected yield of 35% of the final product <jats:italic>trans</jats:italic>‐5,7‐dichloro‐4‐(3‐{4‐[4‐(2‐[<jats:sup>18</jats:sup>F]fluoroethyl)‐piperazin‐1‐yl]‐phenyl}‐ureido)‐1,2,3,4‐tetrahydroquinoline‐2‐carboxylic acid. The biodistribution kinetics of this compound were determined with Sprague Dawley rats <jats:italic>ex vivo</jats:italic> for brain, liver, kidney, and bone. The ligand showed a maximum brain uptake 30 min.p.i. of about 0.1% ID/g. Copyright © 2003 John Wiley &amp; Sons, Ltd.</jats:p>
Autoren
  • Markus Piel
  • Ralf Schirrmacher
  • Sabine Höhnemann
  • Wilhelm Hamkens
  • Beate Kohl
  • Michaela Jansen
  • Ullrich Schmitt
  • Hartmut Lüddens
  • Gerd Dannhardt
  • Frank Rösch
DOI
10.1002/jlcr.682
eISSN
1099-1344
ISSN
0362-4803
Ausgabe der Veröffentlichung
7
Zeitschrift
Journal of Labelled Compounds and Radiopharmaceuticals
Sprache
en
Online publication date
2003
Paginierung
645 - 659
Datum der Veröffentlichung
2003
Status
Published
Herausgeber
Wiley
Herausgeber URL
http://dx.doi.org/10.1002/jlcr.682
Datum der Datenerfassung
2023
Titel
Synthesis and evaluation of 5,7‐dichloro‐4‐(3‐{4‐[4‐(2‐[<sup>18</sup>F]fluoroethyl)‐piperazin‐1‐yl]‐phenyl}‐ureido)‐1,2,3,4‐tetrahydroquinoline‐2‐carboxylic acid as a potential NMDA ligand to study glutamatergic neurotransmission in vivo
Ausgabe der Zeitschrift
46

Datenquelle: Crossref

Autoren
  • Markus Piel
  • Ralf Schirrmacher
  • Sabine Höhnemann
  • Wilhelm Hamkens
  • Beate Kohl
  • Michaela Jansen
  • Ullrich Schmitt
  • Hartmut Lüddens
  • Gerd Dannhardt
  • Frank Rösch
Zeitschrift
Journal of Labelled Compounds and Radiopharmaceuticals: The Official Journal of the International Isotope Society
Artikelnummer
7
Paginierung
645 - 659
Datum der Veröffentlichung
2003
Herausgeber
John Wiley & Sons, Ltd. Chichester, UK
Datum der Datenerfassung
2021
Titel
Synthesis and evaluation of 5, 7-dichloro-4-(3-$$4-[4-(2-[18F] fluoroethyl)-piperazin-1-yl]-phenyl$$-ureido)-1, 2, 3, 4-tetrahydroquinoline-2-carboxylic acid as a potential NMDA ligand to study glutamatergic neurotransmission in vivo
Sub types
  • article
Ausgabe der Zeitschrift
46

Datenquelle: Manual

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