Abstract
In spite of their key role in signal transduction, the mechanism of action of adrenergic receptors is still poorly understood. We have imitated the postulated binding pattern of the large membrane protein with a small, rationally designed synthetic host molecule. Experimental evidence is presented for the simultaneous operation of electrostatic attraction, hydrogen bonds, pi stacking, and hydrophobic interactions. By virtue of this combination of weak attractive forces, adrenaline derivatives in water are bound with high shape selectivity for the slim dopamine skeleton. We think that these findings support the postulated cooperative interplay of noncovalent interactions in the natural receptors. In addition, they provide access to a new type of adrenaline sensor. This may be the first step towards an artificial signal-transduction system.
References
Sep 18, 1992·Journal of Medicinal Chemistry·S Trumpp-KallmeyerM Hibert
Jan 1, 1990·Lung·C M Kessler
Jan 13, 1995·The Journal of Biological Chemistry·V V GurevichJ L Benovic
May 1, 1994·Chemical & Pharmaceutical Bulletin·T IshizuS Noguchi
Dec 1, 1995·Naunyn-Schmiedeberg's Archives of Pharmacology·H PorzigK Thalmeier
Jul 18, 1997·Journal of Chromatography. B, Biomedical Sciences and Applications·W X HuangR V Vivilecchia
Sep 12, 1997·Science·E Pebay-PeyroulaE M Landau
Apr 29, 1998·Science·D A DoyleR MacKinnon
Sep 7, 1999·Bioorganic & Medicinal Chemistry Letters·K OdashimaY Umezawa
Dec 22, 1999·British Journal of Clinical Pharmacology·I B Squire, D B Barnett
Jan 29, 2000·Critical Reviews in Eukaryotic Gene Expression·M Carmo-FonsecaA Calado
Feb 9, 2000·Circulation·M R Bristow
Feb 25, 2000·Cardiovascular Drugs and Therapy·A Himmelmann
Apr 5, 2000·Chemistry : a European Journal·M Herm, T Schrader
Apr 29, 2000·RNA·C MannironiG P Tocchini-Valentini
Aug 5, 2000·Science·K PalczewskiM Miyano
Sep 6, 2000·Pharmacology·S B Liggett
May 2, 1997·The Journal of Organic Chemistry·Lucrecia CampayoAndré Samat
Aug 5, 1997·Chemical Reviews·Jennifer C. Ma, Dennis A. Dougherty
Oct 31, 2002·Angewandte Chemie·Ingo Krossing, Ines Raabe
Dec 17, 1998·Angewandte Chemie·Markus KamiethFrançois Diederich
Sep 4, 1998·Angewandte Chemie·Anthony P Davis, Richard S Wareham
Sep 3, 2001·Angewandte Chemie·Michael HermThomas Schrader
Citations
Nov 23, 2006·Journal of Receptor and Signal Transduction Research·Thomas SchraderManuel Ellermann
Nov 27, 2004·Chemistry : a European Journal·Michael FokkensFrank-Gerrit Klärner
Mar 21, 2007·Angewandte Chemie·Gennady V OshovskyWillem Verboom
Dec 24, 2018·Angewandte Chemie·Meike SapottaFrank Würthner
Mar 8, 2005·Angewandte Chemie·Michael Maue, Thomas Schrader
May 27, 2010·Beilstein Journal of Organic Chemistry·Andreas Späth, Burkhard König
Feb 12, 2020·Chemistry, an Asian Journal·Likun Duan, Yan Zhao
Dec 15, 2011·The Journal of Biological Chemistry·Abdullah MayatiEric Le Ferrec
Sep 6, 2003·Organic & Biomolecular Chemistry·Jessica M KerckhoffsDavid N Reinhoudt
Apr 17, 2014·Chemical Society Reviews·Tuhin PradhanJong Seung Kim
Oct 21, 2011·Chemistry : a European Journal·Olivier PerraudJean-Pierre Dutasta
Oct 31, 2008·Organic Letters·Felipe ReviriegoEnrique Ortí
Dec 21, 2004·Chemistry : a European Journal·Hidetoshi KawaiTakanori Suzuki
Oct 10, 2014·Journal of the American Chemical Society·Takahiro MuraokaKazushi Kinbara
Jul 14, 2005·Journal of the American Chemical Society·Sofiya KolushevaRaz Jelinek
Jan 4, 2006·The Journal of Organic Chemistry·Jeongryul KimKyo Han Ahn
Dec 21, 2006·Journal of the American Chemical Society·Felipe ReviriegoAntonio Domènech
Sep 25, 2004·The Journal of Organic Chemistry·Ana I OlivaJoaquín R Morán
Oct 8, 2004·Organic Letters·Kristen E Secor, Timothy E Glass
Jul 14, 2010·Bioorganic & Medicinal Chemistry Letters·Tao Liu, Zhang-Yu Yu