Document Detail

Adrenaline recognition in water.
MedLine Citation:
PMID:  15352105     Owner:  NLM     Status:  MEDLINE    
Host molecule 1 displays a high affinity in water towards catecholamines and especially related structures such as beta-blockers with extended aromatic pi-faces (up to 7x10(3) M(-1) for each single complexation step or 5x10(7) M(-2) for both steps). The amphiphilic structural design leads to an extensive self-association of host molecules through their aromatic flanks. Above a cmc (critical micelle concentration) of 3x10(-4) M, host 1 forms micelles that produce a favorable microenvironment for hydrophobic interactions with the included guest molecules. Electrostatic attraction of the ammonium alcohol by the phosphonate anions is thus combined with hydrophobic contributions between the aromatic moieties. Ionic hydrogen bonds with polar OH or NH groups of the guest enforce the non-covalent interactions, and finally lead to increased specificity. Both its affinity and its selectivity towards adrenergic receptor substrates are greatly enhanced if the receptor molecule 1 is transferred from water into a lipid monolayer. Catecholamines and beta-blockers lead to drastically different effects at concentrations approaching the micromolar regime. Especially beta-blockers with minute structural changes can be easily distinguished from each other. In both cases, extensive hydrophobic interactions with a self-associated and/or self-organized microenvironment are largely responsible for the observed high efficiency and specificity.
Oliver Molt; Daniel Rübeling; Gerhard Schäfer; Thomas Schrader
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  10     ISSN:  0947-6539     ISO Abbreviation:  Chemistry     Publication Date:  2004 Sep 
Date Detail:
Created Date:  2004-09-07     Completed Date:  2005-12-14     Revised Date:  2009-08-04    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  4225-32     Citation Subset:  IM    
Department of Chemistry, Philipps-Universität Marburg, Hans-Meerwein-Str., 35032 Marburg, Germany.
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MeSH Terms
Adrenergic beta-Antagonists / chemistry
Chemistry, Physical
Epinephrine / chemistry*
Hydrogen Bonding
Magnetic Resonance Spectroscopy
Models, Molecular
Physicochemical Phenomena
Protein Conformation
Receptors, Adrenergic / chemistry
Water / chemistry
Reg. No./Substance:
0/Adrenergic beta-Antagonists; 0/Catecholamines; 0/Micelles; 0/Receptors, Adrenergic; 51-43-4/Epinephrine; 7732-18-5/Water

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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