2002
DOI: 10.1002/1521-3765(20020315)8:6<1485::aid-chem1485>3.0.co;2-h
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Towards Synthetic Adrenaline Receptors—Shape-Selective Adrenaline Recognition in Water

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, π stacking, and hydrophobic interactions. By virtue of this combination of weak attractive forces, adrenaline derivatives in water are bound… Show more

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Cited by 49 publications
(25 citation statements)
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“…The next group of the cleft receptors (8,9) was also designed as a model of adrenergic -receptor [13,14,15]. On the contrary to compound (7), the macrocyclic host (8) [14,15] revealed the shape selectivity towards adrenaline derivatives, such as e.g.…”
Section: Amino Alcohol and Catecholamine Re-ceptorsmentioning
confidence: 99%
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“…The next group of the cleft receptors (8,9) was also designed as a model of adrenergic -receptor [13,14,15]. On the contrary to compound (7), the macrocyclic host (8) [14,15] revealed the shape selectivity towards adrenaline derivatives, such as e.g.…”
Section: Amino Alcohol and Catecholamine Re-ceptorsmentioning
confidence: 99%
“…On the contrary to compound (7), the macrocyclic host (8) [14,15] revealed the shape selectivity towards adrenaline derivatives, such as e.g. Substitution of bridging unit by pyridine-2,6-dicarboxamide (host compound (9)) resulted in diminished binding constants when comparing to (8) (K a for adrenaline hydrochloride equal 153 M -1 and 21 M -1 , for noradrenaline hydrochloride 215 M -1 and 136 M -1 and, for dopamine hydrochloride 246 M -1 and 142 M -1 for receptors (8) and (9), respectively in MeOD/D 2 O (1:1) solution) [15]. The multiple non-covalent interactions such as electrostatic attraction, hydrogen bonding, -stacking and hydrophobic forces were found to be responsible for the recognition process.…”
Section: Amino Alcohol and Catecholamine Re-ceptorsmentioning
confidence: 99%
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“…[4] In this regard, cyclodextrins and cucurbiturils as well as hydrophilic pillararenes and calixarenes evolved as universal hosts for the complexation of drugs,v itamins,f ragrances,a nd other desirable guest molecules. By additionally employing p-p-a nd CÀH-p-interactions for guest encapsulation, cyclophanes are suitable hosts not only for biologically important aromatic molecules such as certain amino acids, [8] nucleotides, [7b, 9] and the neurotransmitters epinephrine or dopamine [10] but also for carbohydrates [11] in water.However,the design of cyclophanes,which possess larger cavities and are composed of dyes,r emains challenging. [6] This holds in particular true for so-called molecular probes which, in addition to ah igh selectivity for the recognition of specific guest molecules,a re required to show as pecific response to the respective analyte such as ac hange in absorbance or fluorescence.…”
mentioning
confidence: 99%
“…[6] This holds in particular true for so-called molecular probes which, in addition to ah igh selectivity for the recognition of specific guest molecules,a re required to show as pecific response to the respective analyte such as ac hange in absorbance or fluorescence. By additionally employing p-p-a nd CÀH-p-interactions for guest encapsulation, cyclophanes are suitable hosts not only for biologically important aromatic molecules such as certain amino acids, [8] nucleotides, [7b, 9] and the neurotransmitters epinephrine or dopamine [10] but also for carbohydrates [11] in water. By additionally employing p-p-a nd CÀH-p-interactions for guest encapsulation, cyclophanes are suitable hosts not only for biologically important aromatic molecules such as certain amino acids, [8] nucleotides, [7b, 9] and the neurotransmitters epinephrine or dopamine [10] but also for carbohydrates [11] in water.…”
mentioning
confidence: 99%