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dc.contributor.authorVan der Walt, M.M.
dc.contributor.authorTerre'Blanche, G.
dc.date.accessioned2017-03-20T08:35:33Z
dc.date.available2017-03-20T08:35:33Z
dc.date.issued2017
dc.identifier.citationVan der Walt, M.M. & Terre'Blanche, G. 2017. Selected C8 two-chain linkers enhance the adenosine A1/A2A receptor affinity and selectivity of caffeine. European journal of medicinal chemistry, 125:652-656. [https://www.journals.elsevier.com/european-journal-of-medicinal-chemistry/]en_US
dc.identifier.issn0223-5234
dc.identifier.issn1768-3254 (Online)
dc.identifier.urihttp://hdl.handle.net/10394/20886
dc.identifier.urihttp://dx.doi.org/10.1016/j.ejmech.2016.09.072
dc.identifier.urihttp://www.sciencedirect.com/science/article/pii/S022352341630808X
dc.description.abstractRecent research exploring C8 substitution on the caffeine core identified 8-(2-phenylethyl)-1,3,7-trimethylxanthine as a non-selective adenosine receptor antagonist. To elaborate further, we included various C8 two-chain-length linkers to enhance adenosine receptor affinity. The results indicated that the unsubstituted benzyloxy linker (1e A1Ki = 1.52 μM) displayed the highest affinity for the A1 adenosine receptor and the para-chloro-substituted phenoxymethyl (1d A2AKi = 1.33 μM) linker the best A2A adenosine receptor affinity. The position of the oxygen revealed that the phenoxymethyl linker favoured A1 adenosine receptor selectivity over the benzyloxy linker and, by introducing a para-chloro substituent, A2A adenosine receptor selectivity was obtained. Selected compounds (1c, 1e) behaved as A1 adenosine receptor antagonists in GTP shift assays and therefore represent selective and non-selective A1 and A2A adenosine receptor antagonists that may have potential for treating neurological disordersen_US
dc.language.isoenen_US
dc.publisherElsevieren_US
dc.subjectCaffeineen_US
dc.subjectAdenosine A2A receptor antagonisten_US
dc.subjectAdenosine A1 receptor antagonisten_US
dc.subject1,3,7-trimethylxanthineen_US
dc.subjectParkinson's diseaseen_US
dc.titleSelected C8 two-chain linkers enhance the adenosine A1/A2A receptor affinity and selectivity of caffeineen_US
dc.typeArticleen_US
dc.contributor.researchID13035134 - Van der Walt, Mietha Magdalena
dc.contributor.researchID10206280 - Terre'Blanche, Gisella


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