Abstract
Herein, we report the synthesis of two phenylaza-[18]crown-6 lariat ethers with a coumarin fluorophore (1 and 2) and we reveal that compound 1 is an excellent probe for K(+) ions under simulated physiological conditions. The presence of a 2-methoxyethoxy lariat group at the ortho position of the anilino moiety is crucial to the substantially increased stability of compounds 1 and 2 over their lariat-free phenylaza-[18]crown-6 ether analogues. Probe 1 shows a high K(+)/Na(+) selectivity and a 2.5-fold fluorescence enhancement was observed in the presence of 100 mM K(+) ions. A fluorescent membrane sensor, which was prepared by incorporating probe 1 into a hydrogel, showed a fully reversible response, a response time of 150 s, and a signal change of 7.8% per 1 mM K(+) within the range 1-10 mM K(+). The membrane was easily fabricated (only a single sensing layer on a solid polyester support), yet no leaching was observed. Moreover, compound 1 rapidly permeated into cells, was cytocompatible, and was suitable for the fluorescent imaging of K(+) ions on both the extracellular and intracellular levels.
| Original language | English |
|---|---|
| Pages (from-to) | 14911-14917 |
| Number of pages | 7 |
| Journal | Chemistry (Weinheim an der Bergstrasse, Germany) |
| Volume | 19 |
| Issue number | 44 |
| DOIs | |
| Publication status | Published - 25 Oct 2013 |
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Keywords
- crown compounds
- fluorescence
- gels
- potassium
- sensors
ASJC Scopus subject areas
- Medicine(all)
Cite this
A highly K(+)-selective phenylaza-[18]crown-6-lariat-ether-based fluoroionophore and its application in the sensing of K+ ions with an optical sensor film and in cells. / Ast, Sandra; Schwarze, Thomas; Müller, Holger; Sukhanov, Aleksey; Michaelis, Stefanie; Wegener, Joachim; Wolfbeis, Otto S.; Körzdörfer, Thomas; Dürkop, Axel; Holdt, Hans Jürgen.
In: Chemistry (Weinheim an der Bergstrasse, Germany), Vol. 19, No. 44, 25.10.2013, p. 14911-14917.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - A highly K(+)-selective phenylaza-[18]crown-6-lariat-ether-based fluoroionophore and its application in the sensing of K+ ions with an optical sensor film and in cells
AU - Ast, Sandra
AU - Schwarze, Thomas
AU - Müller, Holger
AU - Sukhanov, Aleksey
AU - Michaelis, Stefanie
AU - Wegener, Joachim
AU - Wolfbeis, Otto S.
AU - Körzdörfer, Thomas
AU - Dürkop, Axel
AU - Holdt, Hans Jürgen
PY - 2013/10/25
Y1 - 2013/10/25
N2 - Herein, we report the synthesis of two phenylaza-[18]crown-6 lariat ethers with a coumarin fluorophore (1 and 2) and we reveal that compound 1 is an excellent probe for K(+) ions under simulated physiological conditions. The presence of a 2-methoxyethoxy lariat group at the ortho position of the anilino moiety is crucial to the substantially increased stability of compounds 1 and 2 over their lariat-free phenylaza-[18]crown-6 ether analogues. Probe 1 shows a high K(+)/Na(+) selectivity and a 2.5-fold fluorescence enhancement was observed in the presence of 100 mM K(+) ions. A fluorescent membrane sensor, which was prepared by incorporating probe 1 into a hydrogel, showed a fully reversible response, a response time of 150 s, and a signal change of 7.8% per 1 mM K(+) within the range 1-10 mM K(+). The membrane was easily fabricated (only a single sensing layer on a solid polyester support), yet no leaching was observed. Moreover, compound 1 rapidly permeated into cells, was cytocompatible, and was suitable for the fluorescent imaging of K(+) ions on both the extracellular and intracellular levels.
AB - Herein, we report the synthesis of two phenylaza-[18]crown-6 lariat ethers with a coumarin fluorophore (1 and 2) and we reveal that compound 1 is an excellent probe for K(+) ions under simulated physiological conditions. The presence of a 2-methoxyethoxy lariat group at the ortho position of the anilino moiety is crucial to the substantially increased stability of compounds 1 and 2 over their lariat-free phenylaza-[18]crown-6 ether analogues. Probe 1 shows a high K(+)/Na(+) selectivity and a 2.5-fold fluorescence enhancement was observed in the presence of 100 mM K(+) ions. A fluorescent membrane sensor, which was prepared by incorporating probe 1 into a hydrogel, showed a fully reversible response, a response time of 150 s, and a signal change of 7.8% per 1 mM K(+) within the range 1-10 mM K(+). The membrane was easily fabricated (only a single sensing layer on a solid polyester support), yet no leaching was observed. Moreover, compound 1 rapidly permeated into cells, was cytocompatible, and was suitable for the fluorescent imaging of K(+) ions on both the extracellular and intracellular levels.
KW - crown compounds
KW - fluorescence
KW - gels
KW - potassium
KW - sensors
UR - http://www.scopus.com/inward/record.url?scp=84922394333&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84922394333&partnerID=8YFLogxK
U2 - 10.1002/chem.201302350
DO - 10.1002/chem.201302350
M3 - Article
C2 - 24105686
AN - SCOPUS:84885844360
VL - 19
SP - 14911
EP - 14917
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 44
ER -