Anthracene‐Based Cyclophanes with Selective Fluorescent Responses for TTP and GTP: Insights into Recognition and Sensing Mechanisms
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N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry
of Siberian Branch of Russian Academy of Sciences

The paper with the participation of NIOCh's researcher Dr. Aleksandr M. Agafontsev (international collaboration) is published in the journal  Chemistry - A European Journal  (IF 5,16

Anthracene‐Based Cyclophanes with Selective Fluorescent Responses for TTP and GTP: Insights into Recognition and Sensing Mechanisms

Dr. Aleksandr M. Agafontsev, Dr. Tatiana A. Shumilova, Dr. Tobias Rüffer, Prof. Dr. Heinrich Lang, Prof. Dr. Evgeny A. Kataev

Chemistry - A European Journal, 2019, V. 25, N 14, Pp 3541-3549

First published: 15 January 2019


 https://doi.org/10.1002/chem.201806130

chem201900570 toc 0001 m

 

Abstract

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.

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