The benzoxathiolone LYR-71 down-regulates interferon-gamma-inducible pro-inflammatory genes by uncoupling tyrosine phosphorylation of STAT-1 in macrophages

Br J Pharmacol. 2009 Dec;158(8):1971-81. doi: 10.1111/j.1476-5381.2009.00496.x.

Abstract

Background and purpose: Benzoxathiolone derivatives have shown anti-inflammatory and immunomodulatory potential in acne and psoriatic disorders. However, little is known about the molecular basis for these pharmacological effects. In this study, we decided to investigate the anti-inflammatory actions of a benzoxathiolone derivative LYR-71, 6-methyl-2-propylimino-6,7-dihydro-5H-benzo[1,3]oxathiol-4-one, in interferon (IFN)-gamma-activated macrophages.

Experimental approach: RAW 264.7 macrophages or primary macrophages, derived from bone marrow of C3H/HeJ mice, were stimulated with IFN-gamma in the presence of LYR-71. Nitric oxide (NO) or chemokine production was measured by Griess reaction or enzyme-linked immunosorbent assay. RAW 264.7 cells were used to examine the molecular mechanisms of LYR-71 in modulating IFN-gamma-induced inflammatory responses.

Key results: LYR-71 down-regulated IFN-gamma-induced transcription of inducible NO synthase, IFN-gamma-inducible protein-10 and the monokine induced by IFN-gamma genes in macrophages. This effect was mediated by uncoupling tyrosine phosphorylation of the signal transducer and activator of transcription (STAT)-1 in response to IFN-gamma. LYR-71 directly inhibited the in vitro catalytic activity of Janus kinase (JAK)-2. Further, the inhibitory actions of LYR-71 on IFN-gamma-induced STAT-1 phosphorylation and NO production were consistently abolished in the presence of peroxyvanadate, implying another target dependent on protein tyrosine phosphatase.

Conclusions and implications: Taken together, LYR-71 could restrain IFN-gamma-induced inflammatory responses through uncoupling the tyrosine phosphorylation of STAT-1, an activation index of JAK-STAT-1 signalling, in macrophages. These results may provide a molecular mechanism underlying anti-inflammatory actions shown by benzoxathiolone derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / pharmacology
  • Bone Marrow / metabolism
  • Bridged Bicyclo Compounds, Heterocyclic / pharmacology*
  • Cell Line
  • Down-Regulation / drug effects
  • Enzyme-Linked Immunosorbent Assay
  • Imines / pharmacology*
  • Inflammation / drug therapy
  • Inflammation / physiopathology
  • Interferon-gamma / metabolism
  • Macrophages / drug effects*
  • Macrophages / metabolism
  • Male
  • Mice
  • Mice, Inbred C3H
  • Nitric Oxide / metabolism
  • Phosphorylation / drug effects
  • STAT1 Transcription Factor / drug effects*
  • STAT1 Transcription Factor / metabolism
  • Tyrosine / metabolism

Substances

  • Anti-Inflammatory Agents
  • Bridged Bicyclo Compounds, Heterocyclic
  • Imines
  • LYR 71
  • STAT1 Transcription Factor
  • Stat1 protein, mouse
  • Nitric Oxide
  • Tyrosine
  • Interferon-gamma