000865320 001__ 865320
000865320 005__ 20210130003015.0
000865320 0247_ $$2doi$$a10.1055/s-0039-1683491
000865320 037__ $$aFZJ-2019-04822
000865320 041__ $$aGerman
000865320 1001_ $$0P:(DE-Juel1)178654$$aKolks, N.$$b0$$eCorresponding author$$ufzj
000865320 1112_ $$a57. Jahrestagung der Deutschen Gesellschaft für Nuklearmedizin$$cBremen$$d2019-04-03 - 2019-04-06$$gNuklearMedizin 2019$$wGermany
000865320 245__ $$aSynthesis of N-methyl- and 5-HO-[18F]fluorotryptophans
000865320 260__ $$c2019
000865320 3367_ $$033$$2EndNote$$aConference Paper
000865320 3367_ $$2DataCite$$aOther
000865320 3367_ $$2BibTeX$$aINPROCEEDINGS
000865320 3367_ $$2DRIVER$$aconferenceObject
000865320 3367_ $$2ORCID$$aLECTURE_SPEECH
000865320 3367_ $$0PUB:(DE-HGF)6$$2PUB:(DE-HGF)$$aConference Presentation$$bconf$$mconf$$s1569411725_25780$$xAfter Call
000865320 520__ $$aZiel/Aim:Tryptophan (Trp) metabolism is altered in numerous pathological processes. 7-[F-18]FTrp developed in our group is a promising PET-tracer for imaging of Trp metabolism but is unable to distinguish between the two pathways of Trp metabolization. The aim of this project was the development of procedures for the preparation of NinMe-6- and 5-HO-7-[F-18]FTrp as PET-probes suitable for selective visualization of the kynurenine or serotonin pathway.Methodik/Methods:Precursor for the radiosynthesis of NinMe-6-[F-18]FTrp, (S,S)-BPB-Ni-NinMe-6-Bpin-Trp, was synthesized starting from 6-bromoindole. Miyaura borylation, followed by a Mannich reaction and quaternization with MeI furnished N,N,N-(6-Bpin-NinMe-indolyl)methyltrimethylammonium iodide. Alkylation of (S)-BPB-Ni-Gly with the latter and Nin-methylation afforded the desired precursor. Boc-7-Bpin-5-AcO-Trp-OtBu was prepared via Ir-catalyzed 2,7-diborylation of Boc-5-AcO-Trp-OtBu, accessible from 5-OH-Trp in three reaction steps, followed by selective 2-deborylation using Bi(OAc)3. Both precursors were radiolabeled according to the protocol of alcohol-enhanced Cu-mediated F-18-fluorination. The decomposition of the labeled precursors under acidic conditions afforded the F-18-labeled amino acids NinMe-6- and 5-HO-7-[F-18]FTrp.Ergebnisse/Results:(S,S)-BPB-Ni-NinMe-6-Bpin-Trp was obtained in a total yield of 13% after 5 steps and Boc-7-BPin-5-AcO-Trp-OtBu in a 12% yield after 5 steps. (S,S)-BPB-Ni-NinMe-6-[F-18]FTrp was produced in RCCs of up to 90%, decomposed to Nin-Me-6-[F-18]FTrp and isolated by HPLC in RCY of 10 – 15%. Boc-5-OAc-7-Bpin-Trp-OtBu was labeled with an RCC of 25% and after deprotection 5-HO-7-[F-18]FTrp was obtained similarly to NinMe-6-[F-18]FTrp but in lower RCY.Schlussfolgerungen/Conclusions:Nin-Me-6- and 5-HO-7-[F-18]FTrp represent promising PET-probes for the delineation of kynurenine and serotonin pathways of Trp metabolism. Both probes were successfully prepared using alcohol-enhanced Cu-mediated radiofluorination.
000865320 536__ $$0G:(DE-HGF)POF3-573$$a573 - Neuroimaging (POF3-573)$$cPOF3-573$$fPOF III$$x0
000865320 588__ $$aDataset connected to CrossRef Conference
000865320 7001_ $$0P:(DE-HGF)0$$aZlatopolskiy, BD$$b1
000865320 7001_ $$0P:(DE-HGF)0$$aUrusova, EA$$b2
000865320 7001_ $$0P:(DE-Juel1)166419$$aNeumaier, B.$$b3$$ufzj
000865320 773__ $$a10.1055/s-0039-1683491
000865320 909CO $$ooai:juser.fz-juelich.de:865320$$pVDB
000865320 9101_ $$0I:(DE-588b)5008462-8$$6P:(DE-Juel1)178654$$aForschungszentrum Jülich$$b0$$kFZJ
000865320 9101_ $$0I:(DE-588b)5008462-8$$6P:(DE-Juel1)166419$$aForschungszentrum Jülich$$b3$$kFZJ
000865320 9131_ $$0G:(DE-HGF)POF3-573$$1G:(DE-HGF)POF3-570$$2G:(DE-HGF)POF3-500$$3G:(DE-HGF)POF3$$4G:(DE-HGF)POF$$aDE-HGF$$bKey Technologies$$lDecoding the Human Brain$$vNeuroimaging$$x0
000865320 9141_ $$y2019
000865320 920__ $$lyes
000865320 9201_ $$0I:(DE-Juel1)INM-5-20090406$$kINM-5$$lNuklearchemie$$x0
000865320 980__ $$aconf
000865320 980__ $$aVDB
000865320 980__ $$aI:(DE-Juel1)INM-5-20090406
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