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Novel Rhenium Chelate System Derived from Dimercaptosuccinic Acid for the Selective Labeling of Biomolecules

  • This work is part of an effort to develop chelating agents for stable binding and easy conjugation of Re-188 to biologically interesting structures. Starting from the well-known in vivo stability of [188ReO(DMSA)2]-, we want to exploit this coordination system for the design of 188ReO(V) chelates, which are stable toward reoxidation to perrhenate and toward ligand exchange under all conditions of radiopharmaceutical development. Therefore, a new type of tetradentate ligand has been synthesized by bridging two molecules of N,N'-diisobutyl-2,3-dimercaptosuccinamide with N-(3-aminopropyl)propane-1,3-diamine. The resulting stereoisomeric tetrathiolato S4 ligand of composition (iBu)2N(O)C-C(SH)-C(SH)-C(O)NH-(CH2)3-NH-(CH2)3-NHC(O)-C(SH)-C(SH)-C(O)N(iBu)2 forms anionic five-coordinate oxorhenium(V) complexes by a ligand-exchange reaction of NBu4[ReOCl4] in methanol. In the absence of a base, the compounds were isolated as "betaine", [ReO(S4)], with the protonated nitrogen of the bridgeThis work is part of an effort to develop chelating agents for stable binding and easy conjugation of Re-188 to biologically interesting structures. Starting from the well-known in vivo stability of [188ReO(DMSA)2]-, we want to exploit this coordination system for the design of 188ReO(V) chelates, which are stable toward reoxidation to perrhenate and toward ligand exchange under all conditions of radiopharmaceutical development. Therefore, a new type of tetradentate ligand has been synthesized by bridging two molecules of N,N'-diisobutyl-2,3-dimercaptosuccinamide with N-(3-aminopropyl)propane-1,3-diamine. The resulting stereoisomeric tetrathiolato S4 ligand of composition (iBu)2N(O)C-C(SH)-C(SH)-C(O)NH-(CH2)3-NH-(CH2)3-NHC(O)-C(SH)-C(SH)-C(O)N(iBu)2 forms anionic five-coordinate oxorhenium(V) complexes by a ligand-exchange reaction of NBu4[ReOCl4] in methanol. In the absence of a base, the compounds were isolated as "betaine", [ReO(S4)], with the protonated nitrogen of the bridge serving as an internal "counterion". Two representatives have been fully characterized in both the solid and solution states and found to adopt the expected square-pyramidal coordination geometry. The equatorial plane is formed by four thiolate sulfur atoms, whereas the oxygen occupies the apical position. The orientation of the metal oxo group is exo in relation to the carbamido groups in both isomers. Both complexes are stereoisomeric regarding the junction of the triamine chain.zeige mehrzeige weniger

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Metadaten
Autor*innen:T.K. Heinrich, Werner Kraus, H.-J. Pietzsch, C. Smuda, H. Spies
Dokumenttyp:Zeitschriftenartikel
Veröffentlichungsform:Verlagsliteratur
Sprache:Englisch
Titel des übergeordneten Werkes (Englisch):Inorganic Chemistry
Jahr der Erstveröffentlichung:2005
Verlag:American Chemical Society
Verlagsort:Washington, DC
Jahrgang/Band:44
Ausgabe/Heft:26
Erste Seite:9930
Letzte Seite:9937
DOI:10.1021/ic051148s
ISSN:0020-1669
ISSN:1520-510X
Verfügbarkeit des Dokuments:Physisches Exemplar in der Bibliothek der BAM vorhanden ("Hardcopy Access")
Bibliotheksstandort:Sonderstandort: Publica-Schrank
Datum der Freischaltung:19.02.2016
Referierte Publikation:Ja
Datum der Eintragung als referierte Publikation:06.07.2006
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