Novel rhenium complexes derived from alpha-tropanol as potential ligands for the dopamine transporter.
A series of rhenium complexes was synthesized as model compounds for the corresponding radioactive technetium-99m complexes for preliminary biological investigations. In a '3 + 1' mixed-ligand approach the tropanol molecule was linked with the metal core through a omega-mercaptoester group as monodentate ligand. Bis(thioethyl)sulphide was used as the tridentate dithiol ligand to block the remaining free coordination sites. The omega-mercaptoesters were synthesized via the trityl-protected precursors. Binding tests on the cloned human dopamine transporter revealed moderate binding affinities for some of the prepared compounds. The complexes were characterised by X-ray and the lipophilicity as well as pKa values were determined.
Hoepping
A
A
Forschungszentrum Rossendorf, Institut für Bioanorganische und Radiopharmazeutische Chemie, Dresden. hoepping@fz-rossendorf.de
Brust
P
P
Berger
R
R
Leibnitz
P
P
Spies
H
H
Machill
S
S
Scheller
D
D
Johannsen
B
B
D002352:Carrier Proteins / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D003042:Cocaine / Q000031:analogs & derivatives / Q000378:metabolism; D018360:Crystallography, X-Ray; D050483:Dopamine Plasma Membrane Transport Proteins; D006801:Humans; D008562:Membrane Glycoproteins; D026901:Membrane Transport Proteins; D009419:Nerve Tissue Proteins; D010879:Piperazines / Q000378:metabolism; D012211:Rhenium / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014326:Tropanes / Q000737:chemistry* / Q000378:metabolism*
D002352:Carrier Proteins; D050483:Dopamine Plasma Membrane Transport Proteins; D008562:Membrane Glycoproteins; D026901:Membrane Transport Proteins; D009419:Nerve Tissue Proteins; D010879:Piperazines; D014326:Tropanes; C021279:(1R-(exo,exo))-3-(4-fluorophenyl)-8-methyl-8- azabicyclo(3.2.1)octane-2-carboxylic acid, methyl ester; D012211:Rhenium; C043425:vanoxerine; D003042:Cocaine