Near-Infrared Fluorescent Probes with Amine-Incorporated Xanthene Platforms for the Detection of Hypoxia

Three fluorescent probes A, B, and C that function in the near-infrared wavelengths and utilize pseudo xanthene platforms with an oxygen atom at the 10-position replaced by a [Me-N](2-) group have been created to identify hypoxia via nitroreductase determinations at the 0.04, 0.10, and 0.19 ng/mL levels. Theoretical calculations suggest that the probes are not planar due to steric interactions. Absorptions of photons result in the transition of electron density from the indoline moieties to delocalized orbitals on the anthranilic section, ending up on the nitro groups of the electron-poor (i.e., nonreduced) probes (i.e., A, B, and C), whereas those for the more electron-rich (i.e., reduced) probes consisted of movement from the indoline groups to the right side of the anthranilic sections, resulting in a shift in absorption.