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Phosphoinositides and PIPs01:42

Phosphoinositides and PIPs

Phosphoinositides are a group of phospholipids containing a glycerol backbone with two fatty acid chains and a phosphate attached to a myoinositol sugar ring. The inositol head group extends into the cytoplasm, where it is modified by adding phosphate groups to form phosphatidylinositol phosphates or PIPs.
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Membrane lipids such as phosphatidylinositol (PI) are precursors for several membrane-bound and soluble second messengers. Specific kinases phosphorylate PI and produce phosphorylated inositol phospholipids. One such inositol phospholipids are the  phosphatidylinositol-4,5 bisphosphate [PI(4,5)P2], present in the inner half of the lipid bilayer. Upon ligand binding, GPCR stimulates Gq proteins to turn on phospholipase Cꞵ. Activated phospholipase Cꞵ cleaves PI(4,5)P2 and produces two-second...
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Phosphorylation01:02

Phosphorylation

The addition or removal of phosphate groups from proteins is the most common chemical modification that regulates cellular processes. These modifications can affect the structure, activity, stability, and localization of proteins within cells as well as their interactions with other proteins.
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Identification of Mediators of T-cell Receptor Signaling via the Screening of Chemical Inhibitor Libraries
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Identification of Mediators of T-cell Receptor Signaling via the Screening of Chemical Inhibitor Libraries

Published on: January 22, 2019

Phosphorylimidazole derivatives: potentially biosignaling molecules.

Elisa S Orth1, Eduardo H Wanderlind, Michelle Medeiros

  • 1INCT-Catalise, Universidade Federal de Santa Catarina, Florianópolis, SC 88040-900, Brazil.

The Journal of Organic Chemistry
|August 25, 2011
PubMed
Summary

Researchers created stable phosphorylimidazole derivatives from phosphate esters. These molecules have tunable half-lives, showing potential for biological intervention and antibody generation.

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Mimicking the Function of Signaling Proteins: Toward Artificial Signal Transduction Therapy
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Area of Science:

  • Chemical Biology
  • Organic Synthesis

Background:

  • Phosphorylation is a key biological process.
  • Imidazole derivatives are important in biological systems.
  • Developing stable phosphorylated compounds is challenging.

Purpose of the Study:

  • To synthesize and characterize novel phosphorylimidazole derivatives.
  • To investigate the stability and half-lives of these derivatives in aqueous solution.
  • To explore their potential applications in biological interventions.

Main Methods:

  • Phosphorylation of imidazole using activated phosphate diesters and a triester.
  • Analysis and identification using Electrospray Ionization-Tandem Mass Spectrometry (ESI-MS/MS).
  • Structural elucidation using Nuclear Magnetic Resonance (NMR) spectroscopy.

Main Results:

  • Successfully synthesized stable phosphorylimidazole derivatives.
  • Observed and identified derivatives in aqueous solution via ESI-MS/MS and NMR.
  • Determined half-lives ranging from hours to days, with the monoethyl ester exhibiting the longest stability.

Conclusions:

  • Phosphorylimidazole derivatives can be designed with variable, predictable half-lives.
  • These compounds are stable enough for potential use in biological intervention experiments.
  • Potential applications include acting as inhibitors of biosignaling pathways or as haptens for antibody generation.