Novel curcumin analogue 14p protects against myocardial ischemia reperfusion injury through Nrf2-activating anti-oxidative activity

Toxicol Appl Pharmacol. 2015 Jan 15;282(2):175-83. doi: 10.1016/j.taap.2014.12.001. Epub 2014 Dec 10.

Abstract

Background: Alleviating the oxidant stress associated with myocardial ischemia reperfusion has been demonstrated as a potential therapeutic approach to limit ischemia reperfusion (I/R)-induced cardiac damage. Curcumin, a natural compound with anti-oxidative activity, exerts beneficial effect against cardiac I/R injury, but poor chemical and metabolic stability. Previously, we have designed and synthesized a series of mono-carbonyl analogues of curcumin (MACs) with high stability. This study aims to find new anti-oxidant MACs and to demonstrate their effects and mechanisms against I/R-induced heart injury.

Methods: H9c2 cells challenged with H2O2 or TBHP were used for in vitro bio-screening and mechanistic studies. The MDA, H2O2 and SOD levels in H9C2 cells were determined, and the cell viability was assessed by MTT assay. Myocardial I/R mouse models administrated with or without the compound were used for in vivo studies.

Results: The in vitro cell-based screening showed that curcumin analogues 8d and 14p exhibited strong anti-oxidative effects. Pre-treatment of H9c2 cells with 14p activated Nrf2 signaling pathway, attenuated H2O2-increased MDA and SOD level, followed by the inhibition of TBHP-induced cell death and Bax/Bcl-2-caspase-3 pathway activation. Silencing Nrf2 significantly reversed the protective effects of 14p. In in vivo animal model of myocardial I/R, administration of low dose 14p (10mg/kg) reduced infarct size and myocardial apoptosis to the same extent as the high dose curcumin (100mg/kg).

Conclusion: These data support the novel curcumin analogue 14p as a promising antioxidant to decrease oxidative stress and limit myocardial ischemia reperfusion injury via activating Nrf2.

Keywords: Anti-oxidative activity; Cardiac ischemia reperfusion injury; Curcumin; Mono-carbonyl analogues; Nrf2.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antioxidants / pharmacology*
  • Apoptosis / drug effects
  • Caspase 3 / metabolism
  • Curcumin / analogs & derivatives*
  • Curcumin / pharmacology*
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Myocardial Infarction / pathology
  • Myocardial Ischemia / pathology
  • Myocardial Ischemia / prevention & control*
  • Myocardial Reperfusion Injury / pathology
  • Myocardial Reperfusion Injury / prevention & control*
  • Myocardium / pathology
  • NF-E2-Related Factor 2 / metabolism*
  • RNA, Small Interfering / pharmacology

Substances

  • Antioxidants
  • NF-E2-Related Factor 2
  • Nfe2l2 protein, mouse
  • RNA, Small Interfering
  • Caspase 3
  • Curcumin