Tetrahedron p. 5872 - 5879 (2016)
Update date:2022-09-26
Topics:
Yokoo, Hidetomo
Ohsaki, Ayumi
Kagechika, Hiroyuki
Hirano, Tomoya
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.
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Doi:10.1016/j.saa.2014.06.134
(2015)Doi:10.1246/bcsj.60.349
(1987)Doi:10.1016/j.tet.2015.01.050
(2015)Doi:10.1055/s-1985-31098
(1985)Doi:10.1002/ardp.19853180514
(1985)Doi:10.1016/0022-328X(85)87151-5
(1985)