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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Main Authors: | |
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Format: | Article |
Published: |
2021
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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 |
856 | 4 | 0 | |u http://publicatio.bibl.u-szeged.hu/23156/1/EuropeanJOrganicChem-2021-Csomos-AComprehensiveStudyoftheCa2IonBindingofFluorescentlyLabelledBAPTA.pdf |z Dokumentum-elérés |