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Related Concept Videos

Immunofluorescence Microscopy01:12

Immunofluorescence Microscopy

A fluorescence microscope uses fluorescent chromophores called fluorochromes, which can absorb energy from a light source and then emit this energy as visible light. Fluorochromes include naturally fluorescent substances (such as chlorophylls) and fluorescent stains that are added to the specimen to create contrast. Dyes such as Texas red and FITC are examples of fluorochromes. Other examples include the nucleic acid dyes 4’,6’-diamidino-2-phenylindole (DAPI), and acridine orange.
The...

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Autofluorescence Imaging to Evaluate Cellular Metabolism
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Published on: November 15, 2021

Fluorogenic azidofluoresceins for biological imaging.

Peyton Shieh1, Matthew J Hangauer, Carolyn R Bertozzi

  • 1Department of Chemistry, University of California, Berkeley, California 94720, USA.

Journal of the American Chemical Society
|October 3, 2012
PubMed
Summary
This summary is machine-generated.

Researchers developed novel fluorogenic azide probes for bioorthogonal imaging. These probes show enhanced fluorescence upon reaction, enabling selective labeling of proteins and glycoproteins in cells without washing.

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Published on: January 5, 2015

Area of Science:

  • Chemical Biology
  • Organic Chemistry
  • Biomedical Imaging

Background:

  • Bioorthogonal chemical reactions enable specific labeling of biomolecules within complex biological systems.
  • Fluorogenic probes that increase fluorescence upon reaction are ideal for 'no-wash' imaging, reducing background noise.
  • Developing probes with predictable fluorescence enhancement upon bioorthogonal activation remains a challenge.

Purpose of the Study:

  • To rationally design and synthesize novel fluorogenic azide probes activated by bioorthogonal cycloaddition reactions.
  • To identify azidofluorescein derivatives with significant fluorescence enhancement upon reaction with alkynes.
  • To demonstrate the utility of these probes for labeling biomolecules in vitro and in cells under no-wash conditions.

Main Methods:

  • Density functional theory (DFT) calculations to predict fluorescence enhancement of azidofluorescein derivatives.
  • Synthesis and experimental verification of four azidofluorescein derivatives in model reactions.
  • In vitro labeling of alkyne-functionalized proteins and in situ cell imaging of glycoproteins.

Main Results:

  • DFT calculations guided the identification of promising azidofluorescein derivatives.
  • Four synthesized derivatives showed fluorescence enhancement upon reaction with alkynes (Cu-catalyzed or Cu-free).
  • A 4-azidonaphthylfluorescein analogue demonstrated selective labeling of proteins and glycoproteins, enabling cell imaging without washing.

Conclusions:

  • Established a platform for rational design of fluorogenic azide probes for bioorthogonal imaging.
  • Demonstrated the successful application of these probes for selective biomolecule labeling and cell imaging under no-wash conditions.
  • Highlighted the potential for tailoring spectral properties of these probes for diverse biological imaging applications.