Bright Ideas for Chemical Biology

Abstract

Small-molecule fluorescent probes embody an essential facet of chemical biology. Although numerous compounds are known, the ensemble of fluorescent probes is based on a modest collection of modular "core" dyes. The elaboration of these dyes with diverse chemical moieties is enabling the precise interrogation of biochemical and biological systems. The importance of fluorescence-based technologies in chemical biology elicits a necessity to understand the major classes of small-molecule fluorophores. Here, we examine the chemical and photophysical properties of oft-used fluorophores and highlight classic and contemporary examples in which utility has been built upon these scaffolds.

Predicting Efficient Antenna Ligands for Tb(III) Emission

“…Flash silica gel chromatography was performed using Merck 40-70 mesh silica gel. 1 H and 13 C NMR spectra (recorded at ambient temperature on Bruker FT-NMR spectrometers), elemental analyses, and mass spectra were obtained at the corresponding analytical facility in the College of Chemistry, University of California, Berkeley.…”

“…Yield: 152 g (97%). 1 -2-methoxy-1,3-dimethylbenzene (2b). 1 Fluoro-2-hydroxy-1,3-phenylene)dimethanol (4c).…”

“…1 -2-methoxy-1,3-dimethylbenzene (2b). 1 Fluoro-2-hydroxy-1,3-phenylene)dimethanol (4c). 1 in 450 mL of water was added 4e (136 g, 0.81 mmol).…”

“…1 Fluoro-2-hydroxy-1,3-phenylene)dimethanol (4c). 1 in 450 mL of water was added 4e (136 g, 0.81 mmol). Dimethyl sulfate (79.0 ml, 838 mmol) was added to the resulting brown solution, and the reaction mixture was stirred for ~ 30 min.…”

Fluorescent Amino Acids: Modular Building Blocks for the Assembly of New Tools for Chemical Biology

“…[1][2][3] The quest for insight into these ubiquitous biological processes, coupled with the limited range of naturally occurring fluorescent amino acids has led to development of versatile approaches for integrating fluorescent (or pro-fluorescent) motifs into peptides and proteins. 4,5 Currently, one of the most broadly applied methods for covalently labeling a protein with a fluorophore is to co-express the target with a naturally occurring fluorescent protein.…”