Issue 30, 2020

Rational design of small molecule fluorescent probes for biological applications

Abstract

Fluorescent small molecules are powerful tools for visualizing biological events, embodying an essential facet of chemical biology. Since the discovery of the first organic fluorophore, quinine, in 1845, both synthetic and theoretical efforts have endeavored to “modulate” fluorescent compounds. An advantage of synthetic dyes is the ability to employ modern organic chemistry strategies to tailor chemical structures and thereby rationally tune photophysical properties and functionality of the fluorophore. This review explores general factors affecting fluorophore excitation and emission spectra, molar absorption, Stokes shift, and quantum efficiency; and provides guidelines for chemist to create novel probes. Structure–property relationships concerning the substituents are discussed in detail with examples for several dye families. We also present a survey of functional probes based on PeT, FRET, and environmental or photo-sensitivity, focusing on representative recent work in each category. We believe that a full understanding of dyes with diverse chemical moieties enables the rational design of probes for the precise interrogation of biochemical and biological phenomena.

Graphical abstract: Rational design of small molecule fluorescent probes for biological applications

Supplementary files

Article information

Article type
Review Article
Submitted
01 6 2020
Accepted
14 7 2020
First published
21 7 2020

Org. Biomol. Chem., 2020,18, 5747-5763

Author version available

Rational design of small molecule fluorescent probes for biological applications

J. V. Jun, D. M. Chenoweth and E. J. Petersson, Org. Biomol. Chem., 2020, 18, 5747 DOI: 10.1039/D0OB01131B

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