- Structural development of canthin-5,6-dione moiety as a fluorescent dye and its application to novel fluorescent sensors
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Canthin-5,6-dione is a common structure of the fluorescent natural products amarastelline A and nigakinone. Here, we synthesized various derivatives, and studied their fluorescence properties. The effects of substituent groups at the N3-, 4- and 10-positions were clarified. N3-Substitution influenced the solvent-dependent fluorescent change by modulating tautomerization between canthin-5,6-dione and the 5-hydroxy-6-one form. 10-Substitution also influenced the fluorescence, especially in aqueous solution, in combination with N3-substitution. Among the synthesized compounds, 5 showed an ‘OFF-ON-OFF’-type fluorescence change with increase of pH, and therefore served as a novel fluorescent sensor for a specific range of pH. Our findings suggest that canthin-5,6-dione should be useful as a fluorophore moiety for fluorescent labeling of biomolecules and for development of fluorescent probes and sensors.
- Yokoo, Hidetomo,Ohsaki, Ayumi,Kagechika, Hiroyuki,Hirano, Tomoya
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p. 5872 - 5879
(2016/09/07)
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- Synthesis and antitumor activity of canthin-5,6-dione derivatives
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Syntheses of canthin-5,6-dione derivatives have been achieved via one step route starting from their respective β-carbolines. Their synthetic compounds showed antitumor activities against P-388 murine leukemia cells and PC-6 human lung carcinoma cells.
- Koike, Kazuo,Yoshino, Hiroshi,Nikaido, Tamotsu
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p. 315 - 323
(2007/10/03)
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- Synthesis and antitumor activity of javacarboline derivatives
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Syntheses of 12H-pyrido[2,1-a]-[β-carbolin-5-ium bromides (15-27) and 11H-pyrrolo[2,1-a]-β-carbolines (32-35), structurally related to the tetracyclic alkaloid javacarboline (1) have been achieved via 2 steps routes starting from the respective β-carbolines. Their synthetic compounds showed potent antitumor activities against P-388 murine leukemia cells and PC-6 human lung carcinoma cells.
- Yoshino, Hiroshi,Koike, Kazuo,Nikaido, Tamotsu
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p. 281 - 293
(2007/10/03)
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- CANTHIN-6-ONE ALKALOIDS FROM EURYCOMA LONGIFOLIA
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Five new canthin-6-one alkaloids, 9,10-dimethoxycanthin-6-one, 10-hydroxy-9-methoxycanthin-6-one, 11-hydroxy-10-methoxycanthin-6-one, 5,9-dimethoxycanthin-6-one and 9-methoxy-3-methylcanthin-5,6-dione were isolated from the bark and wood of Eurycoma longifolia, along with six known canthin-6-one alkaloids and two known β-carboline alakloids.Their structures were determined from spectroscopic data and other chemical evidence.
- Mitsunaga, Katsuyoshi,Koike, Kazuo,Tanaka, Tomoko,Ohkawa, Youko,Kobayashi, Yuko,et al.
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p. 799 - 802
(2007/10/02)
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