PyrAtes: Modular Organic Salts with Large Stokes Shifts for Fluo-rescence Microscopy

Area of Science:

• Organic chemistry
• Medicinal chemistry
• Biophysics

Background:

• Small-molecule fluorescent agents are crucial in medicine and drug development.
• There is a continuous need for novel fluorophores with improved properties.

Purpose of the Study:

• To report the discovery and development of a novel class of fluorophores, termed PyrAtes.
• To characterize the photophysical properties and synthetic accessibility of PyrAtes.
• To evaluate the utility of PyrAtes in live cell imaging.

Main Methods:

• Synthesis of imidazo[1,2-a]pyridinium triflate derivatives.
• Spectroscopic characterization (absorption, emission, Stokes shift).
• Computational modeling for property prediction.
• Live cell imaging experiments in HEK293 cells.

Main Results:

• A novel class of fluorophores, PyrAtes, was discovered with an imidazo[1,2-a]pyridinium triflate core.
• PyrAtes are synthesized in a single step from readily available materials, with over 60 examples reported.
• These fluorophores exhibit large Stokes shifts (up to 240 nm) and near-infrared emission (up to 720 nm).
• A computational platform was developed to predict emission wavelengths.
• PyrAtes demonstrated compatibility with live cell imaging, functioning as intracellular markers.

Conclusions:

• PyrAtes represent a versatile and readily accessible class of novel fluorophores.
• Their photophysical properties, including large Stokes shifts and NIR emission, make them suitable for various applications.
• PyrAtes show significant potential as intracellular markers for live cell imaging in biomedical research.