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Related Experiment Videos

Fluorophore-labeled S-nitrosothiols.

X Chen1, Z Wen, M Xian

  • 1Department of Chemistry, Wayne State University, Detroit, Michigan 48202, USA.

The Journal of Organic Chemistry
|September 1, 2001
PubMed
Summary
This summary is machine-generated.

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Researchers developed novel fluorescent probes using S-nitrosothiols. These probes show significant fluorescence enhancement upon NO release, enabling sensitive detection of nitric oxide transfer in biological systems.

Area of Science:

  • Chemical Biology
  • Organic Synthesis
  • Biophysical Chemistry

Background:

  • S-nitrosothiols (SNOs) are crucial signaling molecules involved in various physiological processes.
  • Developing sensitive and specific probes for detecting SNOs and their associated nitric oxide (NO) transfer is essential for biological research.

Purpose of the Study:

  • To synthesize and characterize novel fluorophore-labeled S-nitrosothiols for enhanced fluorescence detection.
  • To investigate the mechanism of fluorescence enhancement upon NO group removal.
  • To evaluate the utility of these probes in studying S-nitrosothiol/thiol transnitrosation kinetics and NO transfer in cellular environments.

Main Methods:

  • Synthesis of dansyl-labeled S-nitrosothiols with varying alkyl linkers.
  • Evaluation of fluorescence enhancement via transnitrosation and photolysis.

Related Experiment Videos

  • Ab initio density functional theory (DFT) calculations to understand electronic interactions.
  • Kinetic studies of S-nitrosothiol/thiol transnitrosation.
  • Application as fluorescence probes in human umbilical vein endothelial cells.

    • Main Results:

    • Dansyl-labeled S-nitrosothiols exhibited up to 30-fold fluorescence enhancement upon NO group removal.
    • Fluorescence enhancement is attributed to intramolecular energy transfer from the dansyl fluorophore to the SNO moiety.
    • DFT calculations revealed favorable overlap and stabilizing interactions between the SNO group and dansyl ring, influenced by linker length and sulfonamide rigidity.
    • The probe successfully monitored transnitrosation kinetics and NO transfer in endothelial cells.

    Conclusions:

    • Novel fluorophore-labeled S-nitrosothiols serve as effective fluorescent probes for NO detection.
    • The design strategy, involving intramolecular energy transfer and tunable linker properties, enhances probe sensitivity.
    • These probes offer a valuable tool for investigating NO signaling pathways and S-nitrosothiol chemistry in biological systems.