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

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

Journal

Chemistry - A European Journal
ISSN: 0947-6539 , E-ISSN: 1521-3765

Output data

Year: 2019, Volume: 25, Number: 14, Pages: 3541-3549 Pages count : 9 DOI: 10.1002/chem.201806130

Tags

fluorescence; host–guest systems; macrocycles; nucleotide recognition; receptors; sensors

Authors

Agafontsev A.M. ^1,2,3 , Shumilova T.A. ¹ , Ruffer T. ¹ , Lang H. ¹ , Kataev E.A. ¹

Affiliations

1	(Scopus) Institute of Chemistry, Technische Universit?t Chemnitz, Chemnitz, 09107, Germany
2	(Scopus) N.N. Vorozhtsov Institute of Organic Chemistry SB RAS, 9 Lavrentiev Avenue, Novosibirsk, 630090, Russian Federation
3	(Scopus) Novosibirsk State University, Pirogova St. 1, Novosibirsk, 630090, Russian Federation

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. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Agafontsev A.M. , Shumilova T.A. , Ruffer T. , Lang H. , Kataev E.A.
Anthracene-Based Cyclophanes with Selective Fluorescent Responses for TTP and GTP: Insights into Recognition and Sensing Mechanisms
Chemistry - A European Journal. 2019. V.25. N14. P.3541-3549. DOI: 10.1002/chem.201806130 WOS Scopus РИНЦ

Published online:	Feb 19, 2019
Published print:	Mar 7, 2019

Web of science	WOS:000460692100018
Scopus	2-s2.0-85061919443
Elibrary	38649069
OpenAlex	W2909358018