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Anthracene‐Based Cyclophanes with Selective Fluorescent Responses for TTP and GTP: Insights into Recognition and Sensing Mechanisms
Author(s) -
Agafontsev Aleksandr M.,
Shumilova Tatiana A.,
Rüffer Tobias,
Lang Heinrich,
Kataev Evgeny A.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201806130
Subject(s) - anthracene , chemistry , nucleotide , fluorescence , pyrophosphate , nucleoside , quenching (fluorescence) , nucleoside triphosphate , gtp' , stereochemistry , photochemistry , organic chemistry , biochemistry , physics , quantum mechanics , gene , enzyme
Three anthracene‐based cyclophanes were synthesized and their binding properties towards nucleoside triphosphates were studied. A new polycyclic amine derived from dearomatized anthracene was identified as a major side product in the cyclization reaction between 9,10‐anthracenedicarboxaldehyde and diethylenetriamine. Its structure was determined by single‐crystal X‐ray analysis. The cyclophanes were found to form 1:1 complexes with all nucleoside triphosphates as well as with pyrophosphate in a buffered aqueous solution at pH 6.2. A turn‐on fluorescence response was observed for all nucleotides except for GTP, which demonstrated strong fluorescence quenching. The strongest turn‐on fluorescence was observed for the largest receptor 3 in the presence of thymidine triphosphate (TTP). Based on the NMR and fluorescence experiments, two major binding modes for nucleotide complexes were identified.