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Related Experiment Video

Updated: May 8, 2026

Non-invasive Optical Imaging of the Lymphatic Vasculature of a Mouse

Non-invasive Optical Imaging of the Lymphatic Vasculature of a Mouse

Published on: March 8, 2013

Optimized Red-Absorbing Dyes for Imaging and Sensing.

Jonathan B Grimm¹, Ariana N Tkachuk¹, Ronak Patel¹

¹Janelia Research Campus, Howard Hughes Medical Institute, 19700 Helix Drive, Ashburn, Virginia 20147, United States.

Journal of the American Chemical Society

|October 16, 2023

Summary

This summary is machine-generated.

Researchers optimized rhodamine dyes by tuning their equilibrium for better fluorescence imaging. Structure-activity relationships revealed how substituents control dye properties for applications like single-particle tracking and cAMP sensing.

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Area of Science:

Organic Chemistry
Biophysical Chemistry
Fluorescence Microscopy

Background:

Rhodamine dyes are versatile fluorescent probe scaffolds.
Their function relies on an equilibrium between a colorless lactone and a fluorescent zwitterion.
Optimizing this equilibrium (K_L-Z) is crucial for specific biological applications.

Purpose of the Study:

To elucidate structure-activity relationships governing the rhodamine lactone-zwitterion equilibrium.
To develop a comprehensive collection of rhodamine dyes using novel organic chemistry.
To provide a roadmap for rational design of improved rhodamine dyes.

Main Methods:

Synthesis of a diverse library of rhodamine dyes.
Investigation of structure-activity relationships impacting the lactone-zwitterion equilibrium.
Application of designed dyes in advanced fluorescence imaging techniques.

Main Results:

Auxochrome substituents were identified as key modulators of the lactone-zwitterion equilibrium.
Electron-donating auxochromes and fluorinated phenyl rings yield bright, red-shifted fluorophores for single-particle tracking and multicolor imaging.
N-aryl auxochromes with fluorination produce red-shifted FRET quencher dyes for cAMP sensing via fluorescence lifetime imaging microscopy.

Conclusions:

Established structure-activity relationships for rhodamine dye design.
Expanded synthetic methodologies for rhodamine derivatives.
Generated novel reagents for advanced fluorescence imaging, including live-cell applications and specific analyte sensing.