Ester-Derivatized Indoles as Fluorescent and Infrared Probes for Hydration Environments^†

Tryptophan derivatives have long been used as site-specific biological probes. 4-Cyanotryptophan emits in the visible region and is the smallest blue fluorescent amino acid probe for biological applications. Other indole or tryptophan analogs may emit at even longer wavelengths than 4-cyanotryptophan. We performed FTIR, UV-Vis, and steady-state and time-resolved fluorescence spectroscopy on six ester-derivatized indoles in different solvents. Methyl indole-4-carboxylate emits at 450 nm with a long fluorescence lifetime, and is a promising candidate for a fluorescent probe. The ester-derivatized indoles could be used as spectroscopic probes to study local protein environments. Our measurements provide a guide for choosing esterderivatized indoles to use in practice and data for computational modeling of the effect of substitution on the electronic transitions of indole.