Immunosuppressive activity of endovanilloids: N-arachidonoyl-dopamine inhibits activation of the NF-kappa B, NFAT, and activator protein 1 signaling pathways

J Immunol. 2004 Feb 15;172(4):2341-51. doi: 10.4049/jimmunol.172.4.2341.

Abstract

Endogenous N-acyl dopamines such as N-arachidonoyldopamine (NADA) and N-oleoyldopamine have been recently identified as a new class of brain neurotransmitters sharing endocannabinoid and endovanilloid biological activities. As endocannabinoids show immunomodulatory activity, and T cells play a key role in the onset of several diseases that affect the CNS, we have evaluated the immunosuppressive activity of NADA and N-oleoyldopamine in human T cells, discovering that both compounds are potent inhibitors of early and late events in TCR-mediated T cell activation. Moreover, we found that NADA specifically inhibited both IL-2 and TNF-alpha gene transcription in stimulated Jurkat T cells. To further characterize the inhibitory mechanisms of NADA at the transcriptional level, we examined the DNA binding and transcriptional activities of NF-kappaB, NF-AT, and AP-1 transcription factors in Jurkat cells. We found that NADA inhibited NF-kappaB-dependent transcriptional activity without affecting either degradation of the cytoplasmic NF-kappaB inhibitory protein, IkappaBalpha, or DNA binding activity. However, phosphorylation of the p65/RelA subunit was clearly inhibited by NADA in stimulated cells. In addition, NADA inhibited both binding to DNA and the transcriptional activity of NF-AT and AP-1, as expected from the inhibition of NF-AT1 dephosphorylation and c-Jun N-terminal kinase activation in stimulated T cells. Finally, overexpression of a constitutively active form of calcineurin demonstrated that this phosphatase may represent one of the main targets of NADA. These findings provide new mechanistic insights into the anti-inflammatory activities of NADA and highlight their potential to design novel therapeutic strategies to manage inflammatory diseases.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adult
  • Arachidonic Acids / physiology*
  • Calcineurin / metabolism
  • Calcineurin Inhibitors
  • Cannabinoid Receptor Modulators / physiology*
  • DNA-Binding Proteins / antagonists & inhibitors*
  • DNA-Binding Proteins / physiology
  • Dopamine / analogs & derivatives*
  • Dopamine / physiology*
  • Growth Inhibitors / physiology
  • Humans
  • Immunosuppressive Agents / pharmacology*
  • Interleukin-2 / genetics
  • Jurkat Cells
  • Lymphocyte Activation / drug effects
  • MAP Kinase Kinase 1
  • Mitogen-Activated Protein Kinase Kinases / antagonists & inhibitors
  • Mitogen-Activated Protein Kinase Kinases / metabolism
  • Mitogen-Activated Protein Kinases / antagonists & inhibitors
  • Mitogen-Activated Protein Kinases / metabolism
  • NF-kappa B / antagonists & inhibitors*
  • NF-kappa B / metabolism
  • NF-kappa B / physiology
  • NFATC Transcription Factors
  • Nuclear Proteins*
  • Phosphorylation / drug effects
  • Promoter Regions, Genetic / drug effects
  • Promoter Regions, Genetic / immunology
  • Protein Subunits / antagonists & inhibitors
  • Protein Subunits / metabolism
  • Signal Transduction / drug effects
  • Signal Transduction / immunology*
  • T-Lymphocytes / cytology
  • T-Lymphocytes / drug effects
  • T-Lymphocytes / metabolism
  • Transcription Factor AP-1 / antagonists & inhibitors*
  • Transcription Factor AP-1 / physiology
  • Transcription Factor RelA
  • Transcription Factors / antagonists & inhibitors*
  • Transcription Factors / physiology
  • Transcriptional Activation / drug effects
  • Transcriptional Activation / immunology
  • Tumor Necrosis Factor-alpha / genetics

Substances

  • Arachidonic Acids
  • Calcineurin Inhibitors
  • Cannabinoid Receptor Modulators
  • DNA-Binding Proteins
  • Growth Inhibitors
  • Immunosuppressive Agents
  • Interleukin-2
  • NF-kappa B
  • NFATC Transcription Factors
  • Nuclear Proteins
  • Protein Subunits
  • Transcription Factor AP-1
  • Transcription Factor RelA
  • Transcription Factors
  • Tumor Necrosis Factor-alpha
  • arachidonyl dopamine
  • N-linoleoyldopamine
  • Mitogen-Activated Protein Kinases
  • MAP Kinase Kinase 1
  • MAP2K1 protein, human
  • Mitogen-Activated Protein Kinase Kinases
  • Calcineurin
  • Dopamine