[Synthesis of BODIPY-FL-labeled phenylephrine and the determination of its biological activity]

Beijing Da Xue Xue Bao Yi Xue Ban. 2004 Dec;36(6):623-5.
[Article in Chinese]

Abstract

Objective: To synthesize BODIPY-FL-labeled phenylephrine (BODIPY-FL-PE) and determine its biological activity.

Methods: Condensation of BODIPY-FL (green fluorescence dye) and phenylephrine (alpha1-adrenoceptor agonist) was performed by adding dicyclohexylcarbodiimide (DCC) in the presence of absolute tetrahydrofuran(THF). The reaction occurred in absolutely oxygen and water condition at room temperature. The crude product was separated and purified by thin-layer chromatography (TLC). The structure of BODIPY-FL-PE was characterized by TLC and mass spectrometry (MS). Its pharmabiological activity was determined by Western blot.

Results: BODIPY-FL-PE,the target molecule, was synthesized and its structure was identified by using ultra-violet spectrometry (UV) and MS. The result of Western blot indicated that alpha1-adrenoceptor (alpha1-AR) induced ERK phosphorylation was confirmed in both BODIPY-FL-PE and PE treated groups.

Conclusion: The synthesized BODIPY-FL-PE has pharmacological activity that could activate alpha1-AR. Visualization of AR behaviors could be achieved by tracing the trajectories of BODIPY-FL-PE labeled AR. It might be a promising tool for investigating dynamic behaviors of AR in living cells.

Publication types

  • English Abstract
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adrenergic alpha-1 Receptor Agonists*
  • Adrenergic alpha-Agonists / chemical synthesis
  • Adrenergic alpha-Agonists / chemistry
  • Adrenergic alpha-Agonists / pharmacology
  • Boron Compounds / chemistry*
  • Chromatography, Thin Layer
  • Enzyme Activation / drug effects
  • Extracellular Signal-Regulated MAP Kinases / metabolism
  • Fluorescent Dyes / chemistry
  • Mass Spectrometry
  • Molecular Structure
  • Phenylephrine / chemical synthesis*
  • Phenylephrine / chemistry
  • Phenylephrine / pharmacology*
  • Receptors, Adrenergic, alpha-1 / metabolism
  • Spectrophotometry, Ultraviolet

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Adrenergic alpha-1 Receptor Agonists
  • Adrenergic alpha-Agonists
  • Boron Compounds
  • Fluorescent Dyes
  • Receptors, Adrenergic, alpha-1
  • Phenylephrine
  • Extracellular Signal-Regulated MAP Kinases