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

Результат исследования: Научные публикации в периодических изданияхстатьярецензирование

5 Цитирования (Scopus)

Аннотация

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.

Язык оригиналаанглийский
Страницы (с-по)3541-3549
Число страниц9
ЖурналChemistry - A European Journal
Том25
Номер выпуска14
DOI
СостояниеОпубликовано - 7 мар 2019

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