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Rational design of small molecule fluorescent probes for biological applications

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 30, Pages 5747-5763

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob01131b

Keywords

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Funding

  1. University of Pennsylvania
  2. National Science Foundation [NSF CHE-1708759]
  3. National Institutes of Health [NIH R01-GM118510]

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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.

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