First synthesized in 2013, Xylopyridine represents a class of photoconvertible fluorescent dyes that experience a bathochromic shift in emission upon excitation by ultraviolet light. Methylated Xylopyridine dyes are emissive, cell permeable, water soluble and non- cytotoxic. The Chenoweth lab has shown that the photoconvertibility of these Xylopyridine dyes can be used to label and track proteins of interest through bioorthogonal conjugation and spatiotemporal fluorescence tracking.<br/>Because of Xylopyridine’s desirable cell permeability, water solubility and photoconvertibility, it can serve as a small molecule mimetic of the photoconvertible fluorescent protein (PC-FP) Kaede. Furthermore, because it is a small molecule and not a protein, it has several advantages including exogenous application, minimal perturbativity, resistance to photobleaching, and resistance to oligomerization. Given these advantages, Xylopyridine dyes have the potential to compliment or replace PC-FPs in many established applications.<br/>To develop our understanding and the utility of Xylopyridine dyes, herein is described synthetic efforts to derivatize the Xylopyridine scaffold with the goal of accessing a diverse class of photoconvertible dyes that can be used for modern microscopy applications. Our efforts have focused on introducing steric and electronic perturbations via traditional organic synthetic techniques. We have also employed a unique high throughput discovery method for the rapid diversification of the scaffold. Finally, we have expanded the utility precedent of this fluorescent dye class by labelling and tracking lipids and peptides of biological interest.

Exploration and development of photoconvertible chemical tools

Fall 2022 abstracts, posters, and presentations will launch in mid-September.

ACS Fall 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.