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001025522 245__ $$a8-Bicycloalkyl-CPFPX derivatives as potent and selective tools for in vivo imaging of the A1 adenosine receptor
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001025522 520__ $$aImaging of the A1 adenosine receptor (A1R) by positron emission tomography (PET) with 8-cyclopentyl-3-(3-[18F]fluoropropyl)-1-propyl-xanthine ([18F]CPFPX) has been widely used in preclinical and clinical studies.However, this radioligand suffers from rapid peripheral metabolism and subsequent accumulation of radiometabolites in the vascular compartment. In the present work, we prepared four derivatives of CPFPX byreplacement of the cyclopentyl group with norbornane moieties. These derivatives were evaluated by competition binding studies, microsomal stability assays and LC-MS analysis of microsomal metabolites. In addition, the18F-labeled isotopologue of 8-(1-norbornyl)-3-(3-fluoropropyl)-1-propylxanthine (1-NBX) as the most promising candidate was prepared by radiofluorination of the corresponding tosylate precursor and the resulting radioligand([18F]1-NBX) was evaluated by permeability assays with Caco-2 cells and in vitro autoradiography in rat brain slices. Our results demonstrate that 1-NBX exhibits significantly improved A1R affinity and selectivity whencompared to CPFPX and that it does not give rise to lipophilic metabolites expected to cross the blood-brain-barrier in microsomal assays. Furthermore, [18F]1-NBX showed a high passive permeability (Pc = 6.9 ± 2.9 × 10
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001025522 7001_ $$0P:(DE-Juel1)156407$$aSchneider, Daniela$$b1$$ufzj
001025522 7001_ $$0P:(DE-Juel1)131810$$aBier, Dirk$$b2$$ufzj
001025522 7001_ $$0P:(DE-Juel1)131847$$aSchulze, Annette$$b3$$ufzj
001025522 7001_ $$0P:(DE-Juel1)175142$$aNeumaier, Felix$$b4$$ufzj
001025522 7001_ $$0P:(DE-Juel1)166419$$aNeumaier, Bernd$$b5$$eCorresponding author$$ufzj
001025522 7001_ $$0P:(DE-Juel1)131824$$aHolschbach, Marcus$$b6$$ufzj
001025522 773__ $$0PERI:(DE-600)2005170-0$$a10.1016/j.ejmech.2024.116380$$gVol. 271, p. 116380 -$$p116380$$tEuropean journal of medicinal chemistry$$v271$$x0009-4374$$y2024
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