Pyridinium Analogues of Green Fluorescent Protein Chromophore: Fluorogenic Dyes with Large Solvent-Dependent Stokes Shift

• DOI: 10.1021/acs.jpclett.8b00512
• Publication Date: 2018-03-28T20:20:10Z
• Authors: Yulia G. Ermakova; Tirthendu Sen; Yulia A. Bogdanova; Alexander Yu. Smi...; Nadezhda S. Baleeva; Anna I. Krylov; Mikhail S. Baranov
• Keywords: Chromophore; Solvatochromism; Stokes shift; Quantum yield

Novel fluorogenic dyes based on the GFP chromophore are developed. The compounds contain a pyridinium ring instead of phenolate and feature large Stokes shifts solvent-dependent variations in fluorescence quantum yield. Electronic structure calculations explain trends solvatochromic behavior terms increase dipole moment upon excited-state relaxation polar solvents associated with changes bonding pattern excited state. A unique combination such optical characteristics lipophilic properties enables using one new for imaging membrane endoplasmic reticulum. An extremely high photostability (due to dynamic exchange between free absorbed states) selectivity make this compound promising label type cellular organelles.