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Labeling DNA Probes03:31

Labeling DNA Probes

DNA probes are fragments of DNA labeled with a reporter tag to enable their detection or purification. The resulting labeled DNA probes can then hybridize to target nucleic acid sequences through complementary base-pairing, and may be used to recover or identify these regions.
Radioisotopes, fluorophores, or small molecule binding partners like biotin or digoxigenin, are the most widely used reporter tags for labeling DNA probes. These labels can be attached to the probe DNA molecule via...

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Genetically-encoded Molecular Probes to Study G Protein-coupled Receptors
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Published on: September 13, 2013

Molecular modulated cysteine-selective fluorescent probe.

Hyo Sung Jung1, Tuhin Pradhan, Ji Hye Han

  • 1Department of Chemistry, Korea University, Seoul 136-701, Republic of Korea.

Biomaterials
|August 22, 2012
PubMed
Summary
This summary is machine-generated.

New coumarin probes offer sensitive, turn-on fluorescence detection of cysteine (Cys) over glutathione (GSH). These probes exhibit high selectivity for Cys, enabling accurate intracellular Cys monitoring in HepG2 cells.

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Area of Science:

  • Organic Chemistry
  • Analytical Chemistry
  • Biochemistry

Background:

  • Thiol-containing compounds like cysteine (Cys), glutathione (GSH), and homocysteine (Hcy) are crucial in biological systems.
  • Aberrant levels of these thiols are implicated in various diseases, necessitating sensitive detection methods.
  • Existing fluorescent probes often lack selectivity or exhibit complex reaction mechanisms.

Purpose of the Study:

  • To synthesize and characterize novel coumarin-based fluorescent probes for thiol detection.
  • To investigate the selectivity and sensing mechanism of these probes towards Cys, GSH, and Hcy.
  • To evaluate the probes' efficacy for intracellular Cys detection in HepG2 cells.

Main Methods:

  • Synthesis of coumarin derivatives with varying carboxyl group positions.
  • Fluorescence spectroscopy for analyzing probe response and selectivity.
  • Density Functional Theory (DFT) calculations to elucidate reaction mechanisms.
  • Kinetic studies to determine reaction rates and orders.
  • Cellular experiments using HepG2 cells treated with inhibitors and precursors.

Main Results:

  • Synthesized coumarins (1-3) exhibit turn-on fluorescence via Michael-type addition with thiols.
  • Probes demonstrate high selectivity for Cys over GSH, with selectivity ratios ranging from 48.6 to 111-fold.
  • Probe 1, with an ortho-carboxyl group, shows enhanced selectivity for Cys, potentially due to electronic effects.
  • Intracellular studies confirm probe 1's signal primarily reflects Cys levels, even in the presence of GSH, using BSO treatment and NAC stimulation.

Conclusions:

  • The developed coumarin probes provide a selective and sensitive platform for thiol detection.
  • Probe 1 is particularly effective for specific intracellular Cys quantification.
  • These probes hold promise for applications in biochemical research and diagnostics related to thiol metabolism.