Xie, Sheng-Xue and Petrache, Georgiana and Schneider, Erich and Ye, Qi-Zhuang and Bernhardt, Günther and Seifert, Roland and Buschauer, Armin (2006) Synthesis and pharmacological characterization of novel fluorescent histamine H2-receptor ligands derived from aminopotentidine. Bioorganic & Medicinal Chemistry Letters 16 (15), pp. 3886-3890.
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In an effort to develop a non-radioactive alternative to the [3H]tiotidine and [125I]iodoaminopotentidine binding assays for the histamine H2-receptor (H2R), primary amines related to aminopotentidine were prepared and coupled with the succinimidyl esters of the bulky fluorescent dyes S0536 and BODIPY 650/665-X. The primary amines exhibited different degrees of antagonistic potency at the human and guinea pig H2R. Surprisingly, one compound (5) coupled to the cyanine dye S0536 acted as potent partial agonist/antagonist at the H2R (KB approximately 50 nM; EC50 approximately 100-150 nM). Compounds coupled to the BODIPY dye exhibited moderately high H2R-affinity, too. Thus, the H2R accommodates bulky fluorophores, probably through interaction with extracellular receptor domains. The compounds presented herein provide a starting point for the optimization of fluorescent H2R ligands with respect to affinity and fluorescence as valuable tools to analyze the molecular mechanisms of H2R activation.
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical/Medicinal Chemistry II (Prof. Buschauer)|
|Projects:||GRK 760, Graduiertenkolleg Medizinische Chemie|
|Keywords:||Fluorescent probes; Cyanine; BODIPY; Histamine H2-receptor agonist; GTPase assay|
|Subjects:||500 Science > 570 Life sciences|
600 Technology > 610 Medical sciences Medicine
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Yes|
|Owner:||Prof. Armin Buschauer|
|Deposited On:||21 Feb 2008 08:30|
|Last Modified:||05 Aug 2009 13:42|