Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
Anthracene-Based Cyclophanes with Selective Fluorescent Responses for TTP and GTP : Insights into Recognition and Sensing Mechanisms. / Agafontsev, Aleksandr M.; Shumilova, Tatiana A.; Rüffer, Tobias и др.
в: Chemistry - A European Journal, Том 25, № 14, 07.03.2019, стр. 3541-3549.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - Anthracene-Based Cyclophanes with Selective Fluorescent Responses for TTP and GTP
T2 - Insights into Recognition and Sensing Mechanisms
AU - Agafontsev, Aleksandr M.
AU - Shumilova, Tatiana A.
AU - Rüffer, Tobias
AU - Lang, Heinrich
AU - Kataev, Evgeny A.
N1 - Publisher Copyright: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2019/3/7
Y1 - 2019/3/7
N2 - 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.
AB - 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.
KW - fluorescence
KW - host–guest systems
KW - macrocycles
KW - nucleotide recognition
KW - receptors
KW - sensors
UR - http://www.scopus.com/inward/record.url?scp=85061919443&partnerID=8YFLogxK
U2 - 10.1002/chem.201806130
DO - 10.1002/chem.201806130
M3 - Article
C2 - 30644598
AN - SCOPUS:85061919443
VL - 25
SP - 3541
EP - 3549
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 14
ER -
ID: 18627247