Molecular recognition of creatinine

Bühlmann, Philippe; Badertscher, Martin; Simon, W.

doi:10.1016/s0040-4020(01)86262-1

Cited by 27 publications

(20 citation statements)

References 43 publications

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“…[6][7][8][9][10][11] On the other hand, ionselective electrodes (ISEs) are among the simplest and most robust gauges of ion concentration that are already in use in routine clinical laboratories. [12] Thekey hurdle in the development of ISEs for relatively complex analytes,s uch as creatinine,i st he availability of "ionophores", synthetic receptors that preferentially bind the target molecule.…”

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“…In contrast to its synthetic flat ("two-dimensional") predecessors, [6][7][8][9][10][11] receptor 1 has at hree-dimensional shape and includes the creatinine guest 2 in its aromatic polar cavity by surrounding most of its surface.T he aromatic cavity of 1 is functionalized with as ingle phosphonate group at its open end and four pyrrole NH moieties at the closed end. These polar groups offer complementary hydrogen-bonding interactions to the polar functions of the included guest.…”

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Recognition and Sensing of Creatinine

et al. 2016

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Current methods for creatinine quantification suffer from significant drawbacks when aiming to combine accuracy, simplicity,and affordability.Here,anunprecedented synthetic receptor,a na ryl-substituted calix [4]pyrrole with am onophosphonate bridge,i sr eported that displays remarkable affinity for creatinine and the creatininium cation. The receptor works by including the guest in its deep and polar aromatic cavity and establishing directional interactions in three dimensions.When incorporated into asuitable polymeric membrane, this molecule acts as an ionophore.Ahighly sensitive and selective potentiometric sensor suitable for the determination of creatinine levels in biological fluids,such as urine or plasma, in an accurate,f ast, simple,a nd cost-effective way has thus been developed.Considering the importance of creatinine levels with respect to human health, the methods that are currently available for its quantification are surprisingly suboptimal. Them ost widely used approach is based on the JaffØ method,[1] which was developed more than 100 years ago,a nd is rather complex, tedious,a nd suffers from problems with interference.[2] Alternative enzyme-based assays with either colorimetric or electrochemical detection have become more common during the last decades and have overcome many issues,b ut still show analytical and practical weaknesses. [3] Highly accurate results are obtained by using isotope-dilution gas chromatography mass spectrometry (ID-GC-MS). Unfortunately,t his approach cannot be applied in ah ightraffic routine laboratory. [4,5] In the mid 1990s,supramolecular approaches for the recognition of creatinine began to appear.Thed esigned synthetic receptors comprised an edge functionalized with convergent hydrogen-bonding sites that were complementary to creatinine. [6][7][8][9][10][11] On the other hand, ionselective electrodes (ISEs) are among the simplest and most robust gauges of ion concentration that are already in use in routine clinical laboratories.[12] Thekey hurdle in the development of ISEs for relatively complex analytes,s uch as creatinine,i st he availability of "ionophores", synthetic receptors that preferentially bind the target molecule. [13] Ionophores are responsible for an increase in ISE sensitivity and selectivity.T ot he best of our knowledge,t here are only two examples of neutral synthetic ionophores that are used in the potentiometric analysis of creatinine levels. [14,15] Unfortunately,t he resulting ISEs did not exhibit selectivities and detection limits suitable for the analysis of biological samples.Herein, we introduce an ovel ISE that is suitable for the simple and accurate determination of creatinine levels in body fluids.T his ISE hinges on anovel calix[4]pyrrole-based ionophore, 1,w hich has as trong affinity towards creatinine (2)and the creatinine cation 2·H + (Figure 1). In contrast to its synthetic flat ("two-dimensional") predecessors, [6][7][8][9][10][11] receptor 1 has at hree-dimensional shape and includes the creatinine guest 2 in its ar...

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Recognition and Sensing of Creatinine

et al. 2016

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“…[6][7][8][9][10][11] Accordingly, we have designed a monomer 1 containing one isocytosine unit at each end of an enantiomerically pure C 2 -symmetric angle bar, the bicyclo-[3.3.1]nonane system ( Figure 1, bottom left). Molecular modeling at the semi-empirical level (see the Supporting Information) indicated that a cyclic tetramer 1 4 is favored and that its quadratic cavity would have a width of approximately 13 from face to face in hetero-and homotautoleptic aggregation ( Figure 3).…”

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Topology Selection and Tautoleptic Aggregation: Formation of an Enantiomerically Pure Supramolecular Belt over a Helix

Orentas¹,

Wallentin²,

Bergquist³

et al. 2011

Angew Chem Int Ed

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“…[6][7][8][9][10][11] Accordingly, we have designed a monomer 1 containing one isocytosine unit at each end of an enantiomerically pure C 2 -symmetric angle bar, the bicyclo-[3.3.1]nonane system ( Figure 1, bottom left). [6][7][8][9][10][11] Accordingly, we have designed a monomer 1 containing one isocytosine unit at each end of an enantiomerically pure C 2 -symmetric angle bar, the bicyclo-[3.3.1]nonane system ( Figure 1, bottom left).…”

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