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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 изданияхстатьяРецензирование

Harvard

Agafontsev, AM, Shumilova, TA, Rüffer, T, Lang, H & Kataev, EA 2019, 'Anthracene-Based Cyclophanes with Selective Fluorescent Responses for TTP and GTP: Insights into Recognition and Sensing Mechanisms', Chemistry - A European Journal, Том. 25, № 14, стр. 3541-3549. https://doi.org/10.1002/chem.201806130

APA

Vancouver

Agafontsev AM, Shumilova TA, Rüffer T, Lang H, Kataev EA. Anthracene-Based Cyclophanes with Selective Fluorescent Responses for TTP and GTP: Insights into Recognition and Sensing Mechanisms. Chemistry - A European Journal. 2019 март 7;25(14):3541-3549. doi: 10.1002/chem.201806130

Author

Agafontsev, Aleksandr M. ; Shumilova, Tatiana A. ; Rüffer, Tobias и др. / Anthracene-Based Cyclophanes with Selective Fluorescent Responses for TTP and GTP : Insights into Recognition and Sensing Mechanisms. в: Chemistry - A European Journal. 2019 ; Том 25, № 14. стр. 3541-3549.

BibTeX

@article{89c4e99913484cad8b374a19b9fcfaa6,
title = "Anthracene-Based Cyclophanes with Selective Fluorescent Responses for TTP and GTP: Insights into Recognition and Sensing Mechanisms",
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",
author = "Agafontsev, {Aleksandr M.} and Shumilova, {Tatiana A.} and Tobias R{\"u}ffer and Heinrich Lang and Kataev, {Evgeny A.}",
note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",
year = "2019",
month = mar,
day = "7",
doi = "10.1002/chem.201806130",
language = "English",
volume = "25",
pages = "3541--3549",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "14",

}

RIS

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