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

Aleksandr M Agafontsev; Tatiana A Shumilova; Tobias Rüffer; Heinrich Lang; Evgeny A Kataev

doi:10.1002/chem.201806130

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

Chemistry. 2019 Mar 7;25(14):3541-3549. doi: 10.1002/chem.201806130. Epub 2019 Feb 19.

Authors

Aleksandr M Agafontsev^{1

2

3}, Tatiana A Shumilova¹, Tobias Rüffer¹, Heinrich Lang¹, Evgeny A Kataev¹

Affiliations

¹ Institute of Chemistry, Technische Universität Chemnitz, 09107, Chemnitz, Germany.
² N.N. Vorozhtsov Institute of Organic Chemistry SB RAS, 9 Lavrentiev Avenue, 630090, Novosibirsk, Russia.
³ Novosibirsk State University, Pirogova St. 1, 630090, Novosibirsk, Russia.

PMID: 30644598
DOI: 10.1002/chem.201806130

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.

Keywords: fluorescence; host-guest systems; macrocycles; nucleotide recognition; receptors; sensors.

Grants and funding

3444/12-1/DFG