Improving the Brightness of Pyronin Fluorophore Systems Through Quantum-Mechanical Predictions

Overview

Journal J Phys Chem Lett

Publisher American Chemical Society

Specialty Chemistry

Date 2022 Aug 30

PMID 36040023

Authors

Brandon Walls

Olabisi Suleiman

Carlos Arambula

Alyssa Hall

Olajumoke Adeyiga

Fadel Boumelhem

Jungjae Koh

Samuel O Odoh

Zachary R Woydziak

Affiliations

Soon will be listed here.

Abstract

The pyronin class of fluorophores serves a critical role in numerous imaging applications, particularly involving preferential staining of RNA through base pair intercalation. Despite this important role in molecular staining applications, the same set of century-old pyronins (i.e., pyronin Y (PY) and pyronin B (PB)), which possess relatively low fluorophore brightness, are still predominantly being used due to the lack of methodology for generating enhanced variants. Here, we use TD-DFT calculations of interconversion energies between structures on the S surface as a preliminary means to evaluate fluorophore brightness for a proposed set of pyronins containing variable substitution patterns at the 2, 3, 6, and 7 positions. Using a nucleophilic aromatic substitution/hydride addition approach, we synthesized the same set of pyronins and demonstrate that quantum-mechanical computations are useful for predicting fluorophore performance. We produced the brightest series of pyronin fluorophores described to date, which possess considerable gains over PY and PB.

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