Abstract
6-Methoxy-4-quinolone (6-MOQ, 1), an oxidation product derived from 5-methoxyindole-3-acetic acid, is a novel fluorophore, which has several useful characteristics for biomedical analysis. Compound 1 has strong fluorescence with a large Stokes' shift in aqueous media, and the maximum fluorescence excitation and emission wavelengths are 243 nm and 374 nm, respectively. The molar absorptivity at the maximum excitation wavelength and fluorescence quantum yield in aqueous 10% (v/v) methanol are 32 600 L mol -1 cm -1 and 0.38, respectively. The fluorescence intensity of 1 is scarcely affected by changing the medium pH, showing strong fluorescence from pH 2.0 to 11.0. In addition, 1 is highly stable against light and heat, and no degradation was observed at 60°C for 3 days with exposure to daylight. As a fluorescent labeling reagent, [(6-methoxy-4-oxo-1,4-dihydroquinolin-3-yl)methyl]amine (6-MOQ-NH 2, 2) was synthesized, and determination of carboxylic acids was demonstrated; 50 pmol of standard propionic acid and isobutyric acid were derivatized, and the obtained S/N ratios for 10 fmol (injection amount) of these two acids were 206 and 164, respectively.
| Original language | English |
|---|---|
| Pages (from-to) | 225-231 |
| Number of pages | 7 |
| Journal | Journal of Chromatography A |
| Volume | 1059 |
| Issue number | 1-2 |
| DOIs | |
| Publication status | Published - Dec 3 2004 |
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All Science Journal Classification (ASJC) codes
- Analytical Chemistry
- Biochemistry
- Organic Chemistry
Cite this
Novel stable fluorophore, 6-methoxy-4-quinolone, with strong fluorescence in wide pH range of aqueous media, and its application as a fluorescent labeling reagent. / Hirano, Junzo; Hamase, Kenji; Fukuda, Hiroko; Tomita, Tatsunosuke; Zaitsu, Kiyoshi.
In: Journal of Chromatography A, Vol. 1059, No. 1-2, 03.12.2004, p. 225-231.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Novel stable fluorophore, 6-methoxy-4-quinolone, with strong fluorescence in wide pH range of aqueous media, and its application as a fluorescent labeling reagent
AU - Hirano, Junzo
AU - Hamase, Kenji
AU - Fukuda, Hiroko
AU - Tomita, Tatsunosuke
AU - Zaitsu, Kiyoshi
PY - 2004/12/3
Y1 - 2004/12/3
N2 - 6-Methoxy-4-quinolone (6-MOQ, 1), an oxidation product derived from 5-methoxyindole-3-acetic acid, is a novel fluorophore, which has several useful characteristics for biomedical analysis. Compound 1 has strong fluorescence with a large Stokes' shift in aqueous media, and the maximum fluorescence excitation and emission wavelengths are 243 nm and 374 nm, respectively. The molar absorptivity at the maximum excitation wavelength and fluorescence quantum yield in aqueous 10% (v/v) methanol are 32 600 L mol -1 cm -1 and 0.38, respectively. The fluorescence intensity of 1 is scarcely affected by changing the medium pH, showing strong fluorescence from pH 2.0 to 11.0. In addition, 1 is highly stable against light and heat, and no degradation was observed at 60°C for 3 days with exposure to daylight. As a fluorescent labeling reagent, [(6-methoxy-4-oxo-1,4-dihydroquinolin-3-yl)methyl]amine (6-MOQ-NH 2, 2) was synthesized, and determination of carboxylic acids was demonstrated; 50 pmol of standard propionic acid and isobutyric acid were derivatized, and the obtained S/N ratios for 10 fmol (injection amount) of these two acids were 206 and 164, respectively.
AB - 6-Methoxy-4-quinolone (6-MOQ, 1), an oxidation product derived from 5-methoxyindole-3-acetic acid, is a novel fluorophore, which has several useful characteristics for biomedical analysis. Compound 1 has strong fluorescence with a large Stokes' shift in aqueous media, and the maximum fluorescence excitation and emission wavelengths are 243 nm and 374 nm, respectively. The molar absorptivity at the maximum excitation wavelength and fluorescence quantum yield in aqueous 10% (v/v) methanol are 32 600 L mol -1 cm -1 and 0.38, respectively. The fluorescence intensity of 1 is scarcely affected by changing the medium pH, showing strong fluorescence from pH 2.0 to 11.0. In addition, 1 is highly stable against light and heat, and no degradation was observed at 60°C for 3 days with exposure to daylight. As a fluorescent labeling reagent, [(6-methoxy-4-oxo-1,4-dihydroquinolin-3-yl)methyl]amine (6-MOQ-NH 2, 2) was synthesized, and determination of carboxylic acids was demonstrated; 50 pmol of standard propionic acid and isobutyric acid were derivatized, and the obtained S/N ratios for 10 fmol (injection amount) of these two acids were 206 and 164, respectively.
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U2 - 10.1016/j.chroma.2004.10.020
DO - 10.1016/j.chroma.2004.10.020
M3 - Article
C2 - 15628146
AN - SCOPUS:9144241206
VL - 1059
SP - 225
EP - 231
JO - Journal of Chromatography A
JF - Journal of Chromatography A
SN - 0021-9673
IS - 1-2
ER -