Water-soluble Nile Blue derivatives: syntheses and photophysical properties.
Four water-soluble 2-hydroxy-Nile Blue derivatives, 1 a, 1 b, 2 a, and 2 b, were prepared by condensation reactions performed under relatively mild conditions (90 degrees C, N,N-dimethylformamide with no added acid). These fluorescent probes had more favorable fluorescence characteristics than two known water-soluble Nile Blue derivatives. Specifically, they were superior to the known dyes with respect to their quantum yields in aqueous media and the sharpness of their fluorescence emissions. Concentration-dependant UV absorption and fluorescence emission studies indicated that the dyes did not aggregate in aqueous solution at concentrations of less than 1-4 microM. The new water-soluble materials 1 a, 1 b, 2 a, and 2 b emit in a desirable region of the fluorescence spectrum (lambda=670-675 nm). Overall they are potentially interesting for labeling biomolecules in aqueous environments.
Jose
Jiney
J
Department of Chemistry, Texas A&M University, Box 30012, College Station, TX 77841, USA.
Ueno
Yuichiro
Y
Burgess
Kevin
K
D000042:Absorption; D000627:Aminophenols / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D006878:Hydroxides / Q000737:chemistry; D009284:Naphthols / Q000737:chemistry; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D012995:Solubility; D013050:Spectrometry, Fluorescence; D014867:Water / Q000737:chemistry*
D000627:Aminophenols; D005456:Fluorescent Dyes; D006878:Hydroxides; D009284:Naphthols; D010078:Oxazines; D014867:Water; C008619:Nile Blue; C031356:hydroxide ion