A comprehensive study of the Ca2+ ion binding of fluorescently labelled BAPTA analogues

Since its development, the ionophore BAPTA (1,2?bis(2?aminophenoxy)-ethane?N,N,N?,N??tetraacetic acid) has been used unchanged in calcium sensing applications. In this work we present a comprehensive experimental and theoretical study of novel alterations in the structure of BAPTA, with a focus on t...

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Bibliographic Details
Main Authors: Csomos Attila
Kontra Bence
Jancsó Attila
Galbács Gábor
Deme Ruth
Kele Zoltán
Rózsa J. Balázs
Kovács Ervin
Mucsi Zoltán
Format: Article
Published: 2021
Series:EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2021 No. 37
Subjects:
doi:10.1002/ejoc.202100948

mtmt:32187933
Online Access:http://publicatio.bibl.u-szeged.hu/23156
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520 3 |a Since its development, the ionophore BAPTA (1,2?bis(2?aminophenoxy)-ethane?N,N,N?,N??tetraacetic acid) has been used unchanged in calcium sensing applications. In this work we present a comprehensive experimental and theoretical study of novel alterations in the structure of BAPTA, with a focus on the systematic modification of the chain connecting the two aromatic rings of the molecule (denoted as ?linker?). A bis-(diethylamino)xantene fluorophore was also attached to the structures in a fixed position and the structure-fluorescence response relationship of these molecules was investigated in addition. The effect of the length of the linker, the number of O atoms in this chain and even the removal of one of the rings was tested; these all proved to significantly alter the characteristics of the compounds. For example, it was found that the second aromatic ring of BAPTA is not essential for the turn-on of the fluorescence. We also demonstrated that successful sensing can be realized even by replacing the chain with a single oxygen atom, which suggests the availability of a new calcium binding mode of the chelator. The reliable turn-on characteristic, the steep Ca 2+ fluorescence titration curve and the intense fluorescence emission combine to make this compound a prospective candidate as a calcium sensing molecular probe in diagnostic neurobiological applications. 
650 4 |a Kémiai tudományok 
700 0 1 |a Kontra Bence  |e aut 
700 0 1 |a Jancsó Attila  |e aut 
700 0 1 |a Galbács Gábor  |e aut 
700 0 1 |a Deme Ruth  |e aut 
700 0 1 |a Kele Zoltán  |e aut 
700 0 2 |a Rózsa J. Balázs  |e aut 
700 0 2 |a Kovács Ervin  |e aut 
700 0 2 |a Mucsi Zoltán  |e aut 
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