A designed protein binding-pocket to control excited-state intramolecular proton transfer fluorescence

Excited-state intramolecular proton transfer involves a photochemical isomerization and creates the opportunity for the emission of two distinct wavelengths of light from a single fluorophore. The selectivity between these two wavelengths of emission is dependent on the environment around the fluoro...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-01, Vol.17 (5), p.1076-1080
Main Authors: Lampkin, Bryan J, Monteiro, Cecilia, Powers, Evan T, Bouc, Paige M, Kelly, Jeffery W, VanVeller, Brett
Format: Article
Language:English
Subjects:
Binding
Binding Sites
Chemical compounds
Emission
Fluorescence
Fluorescent Dyes - chemistry
Fluorophores
Hydrogen Bonding
Isomerization
Microenvironments
Photochemicals
Protein Binding
Proteins
Proteins - chemistry
Protons
Selectivity
Spectrometry, Fluorescence
Wavelengths
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Summary:Excited-state intramolecular proton transfer involves a photochemical isomerization and creates the opportunity for the emission of two distinct wavelengths of light from a single fluorophore. The selectivity between these two wavelengths of emission is dependent on the environment around the fluorophore and suggests the possibility for ratiometric monitoring of protein microenvironments. Unfortunately, nonspecific binding of ESIPT fluorophores does not often lead to dramatic changes in the ratio between the two wavelengths of emission. A protein binding pocket was designed to selectively discriminate between the two channels of emission available to an ESIPT fluorophore. This work is significant because it demonstrates that specific interactions between the protein and the fluorophore are essential to realize strong ratiometric differences between the two possible wavelengths of emission. The design strategies proposed here lead to an ESIPT fluorophore that can discern subtle differences in the interface between two proteins.
ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/c8ob02673d