Near-infrared fluorescent pH-sensitive probes via unexpected barbituric acid mediated synthesis.
Novel near-infrared pyrimidine-fused pH fluorescent probes were prepared by an unusual barbiturate-mediated debenzoindolation and subsequent heteroannulation. A plausible mechanistic pathway is proposed, and the final structures were further elucidated by 2D-NMR. All new compounds are highly fluorescent in the near-infrared region and possess excellent spectral sensitivities to environmental pH changes.
Lee
Hyeran
H
Department of Radiology, Washington University, St. Louis, Missouri 63110, USA.
Berezin
Mikhail Y
MY
Guo
Kevin
K
Kao
Jeff
J
Achilefu
Samuel
S
D001463:Barbiturates / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D015203:Reproducibility of Results; D012680:Sensitivity and Specificity; D019265:Spectroscopy, Near-Infrared; D013237:Stereoisomerism
D001463:Barbiturates; D005456:Fluorescent Dyes; C032232:barbituric acid