Abstract
The construction of supramolecular recognition systems based on specific host-guest interactions has been studied in order to design selective chemical sensors. In this study, guest-responsive receptors for ATP have been designed with cyclodextrins (CyDs) as a basic prototype of the turn-on type fluorescent indicator. We synthesized dipicolylamine (DPA)-modified CyD-Cu2+ complexes (Cu1α, Cu1β, and Cu1γ), and evaluated their recognition capabilities toward phosphoric acid derivatives in water. The UV-Vis absorption and fluorescence spectra revealed that Cu1β selectively recognized ATP over other organic and inorganic phosphates, and that β-CyD had the most suitable cavity size for complexation with ATP. The 1D and 2D NMR analyses suggested that the ATP recognition was based on the host-guest interaction between the adenine moiety of ATP and the CyD cavity, as well as the recognition of phosphoric moieties by the Cu2+-DPA complex site. The specific interactions between the CyD cavity and the nucleobases enabled us to distinguish ATP from other nucleoside triphosphates, such as guanosine triphosphate (GTP), uridine triphosphate (UTP), and cytidine triphosphate (CTP). This study clarified the basic mechanisms of molecular recognition by modified CyDs, and suggested the potential for further application of CyDs in the design of highly selective supramolecular recognition systems for certain molecular targets in water.
| Original language | English |
|---|---|
| Article number | 635 |
| Journal | Molecules |
| Volume | 23 |
| Issue number | 3 |
| DOIs | |
| Publication status | Published - 2018 Jan 1 |
| Externally published | Yes |
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Keywords
- ATP recognition
- Cyclodextrin
- Host-guest interaction
- NMR analyses
- Supramolecular chemistry
ASJC Scopus subject areas
- Analytical Chemistry
- Chemistry (miscellaneous)
- Molecular Medicine
- Pharmaceutical Science
- Drug Discovery
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
Development of dipicolylamine-modified cyclodextrins for the design of selective guest-responsive receptors for atp. / Yamada, Tatsuru; Fujiwara, Shoji; Fujita, Kyohhei; Tsuchido, Yuji; Hashimoto, Takeshi; Hayashita, Takashi.
In: Molecules, Vol. 23, No. 3, 635, 01.01.2018.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Development of dipicolylamine-modified cyclodextrins for the design of selective guest-responsive receptors for atp
AU - Yamada, Tatsuru
AU - Fujiwara, Shoji
AU - Fujita, Kyohhei
AU - Tsuchido, Yuji
AU - Hashimoto, Takeshi
AU - Hayashita, Takashi
PY - 2018/1/1
Y1 - 2018/1/1
N2 - The construction of supramolecular recognition systems based on specific host-guest interactions has been studied in order to design selective chemical sensors. In this study, guest-responsive receptors for ATP have been designed with cyclodextrins (CyDs) as a basic prototype of the turn-on type fluorescent indicator. We synthesized dipicolylamine (DPA)-modified CyD-Cu2+ complexes (Cu1α, Cu1β, and Cu1γ), and evaluated their recognition capabilities toward phosphoric acid derivatives in water. The UV-Vis absorption and fluorescence spectra revealed that Cu1β selectively recognized ATP over other organic and inorganic phosphates, and that β-CyD had the most suitable cavity size for complexation with ATP. The 1D and 2D NMR analyses suggested that the ATP recognition was based on the host-guest interaction between the adenine moiety of ATP and the CyD cavity, as well as the recognition of phosphoric moieties by the Cu2+-DPA complex site. The specific interactions between the CyD cavity and the nucleobases enabled us to distinguish ATP from other nucleoside triphosphates, such as guanosine triphosphate (GTP), uridine triphosphate (UTP), and cytidine triphosphate (CTP). This study clarified the basic mechanisms of molecular recognition by modified CyDs, and suggested the potential for further application of CyDs in the design of highly selective supramolecular recognition systems for certain molecular targets in water.
AB - The construction of supramolecular recognition systems based on specific host-guest interactions has been studied in order to design selective chemical sensors. In this study, guest-responsive receptors for ATP have been designed with cyclodextrins (CyDs) as a basic prototype of the turn-on type fluorescent indicator. We synthesized dipicolylamine (DPA)-modified CyD-Cu2+ complexes (Cu1α, Cu1β, and Cu1γ), and evaluated their recognition capabilities toward phosphoric acid derivatives in water. The UV-Vis absorption and fluorescence spectra revealed that Cu1β selectively recognized ATP over other organic and inorganic phosphates, and that β-CyD had the most suitable cavity size for complexation with ATP. The 1D and 2D NMR analyses suggested that the ATP recognition was based on the host-guest interaction between the adenine moiety of ATP and the CyD cavity, as well as the recognition of phosphoric moieties by the Cu2+-DPA complex site. The specific interactions between the CyD cavity and the nucleobases enabled us to distinguish ATP from other nucleoside triphosphates, such as guanosine triphosphate (GTP), uridine triphosphate (UTP), and cytidine triphosphate (CTP). This study clarified the basic mechanisms of molecular recognition by modified CyDs, and suggested the potential for further application of CyDs in the design of highly selective supramolecular recognition systems for certain molecular targets in water.
KW - ATP recognition
KW - Cyclodextrin
KW - Host-guest interaction
KW - NMR analyses
KW - Supramolecular chemistry
UR - http://www.scopus.com/inward/record.url?scp=85044264927&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85044264927&partnerID=8YFLogxK
U2 - 10.3390/molecules23030635
DO - 10.3390/molecules23030635
M3 - Article
C2 - 29534528
AN - SCOPUS:85044264927
VL - 23
JO - Molecules
JF - Molecules
SN - 1420-3049
IS - 3
M1 - 635
ER -