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Synthesis of new p-tert-butylcalix[4]arene-based polyammonium triazolyl amphiphiles and their binding with nucleoside phosphates.


ABSTRACT: The synthesis of new calix[4]arenes adopting a cone stereoisomeric form bearing two or four azide fragments on the upper rim and water-soluble triazolyl amphiphilic receptors with two or four polyammonium headgroups via copper-catalyzed azide-alkyne cycloaddition reaction has been performed for the first time. It was found that the synthesized macrocycles form stable aggregates with hydrodynamic diameters between 150-200 nm and electrokinetic potentials about +40 to +60 mV in water solutions. Critical aggregation concentration (CAC) values were measured using a micelle method with pyrene and eosin Y as dye probes. The CAC values of tetraalkyl-substituted macrocycles 12a,b (5 µM for both) are significantly lower than those for dialkyl-substituted macrocycles 10a,b (790 and 160 µM, respectively). Premicellar aggregates of macrocycles 10a,b and 12a,b with the dye eosin Y were used for nucleotides sensing through a dye replacement procedure. It is unusual that disubstituted macrocycles 10a,b bind more effectively a less charged adenosine 5'-diphosphate (ADP) than adenosine 5'-triphosphate (ATP). A simple colorimetric method based on polydiacetylene vesicles decorated with 10b was elaborated for the naked-eye detection of ADP with a detection limit of 0.5 mM.

SUBMITTER: Burilov VA 

PROVIDER: S-EPMC6122204 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Synthesis of new <i>p-tert</i>-butylcalix[4]arene-based polyammonium triazolyl amphiphiles and their binding with nucleoside phosphates.

Burilov Vladimir A VA   Fatikhova Guzaliya A GA   Dokuchaeva Mariya N MN   Nugmanov Ramil I RI   Mironova Diana A DA   Dorovatovskii Pavel V PV   Khrustalev Victor N VN   Solovieva Svetlana E SE   Antipin Igor S IS  

Beilstein journal of organic chemistry 20180731


The synthesis of new calix[4]arenes adopting a <i>cone</i> stereoisomeric form bearing two or four azide fragments on the upper rim and water-soluble triazolyl amphiphilic receptors with two or four polyammonium headgroups via copper-catalyzed azide-alkyne cycloaddition reaction has been performed for the first time. It was found that the synthesized macrocycles form stable aggregates with hydrodynamic diameters between 150-200 nm and electrokinetic potentials about +40 to +60 mV in water soluti  ...[more]

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