Synthesis and cardiomyocyte protection activity of crocetin diamide derivatives

Fitoterapia. 2017 Sep:121:106-111. doi: 10.1016/j.fitote.2017.06.014. Epub 2017 Jun 15.

Abstract

A series of novel diamide derivatives (2-8) of crocetin (1) were synthesized and evaluated for their cardioprotective activity in vitro. Using well-established model of hypoxia-induced injury in H9c2 cells, we investigated the effects of 9 compounds and positive drug nicorandil on cellular cytotoxicity by MTT assay, mitochondrial viable staining, LDH activity and mitochondrial membrane potential (MMP). Among the new derivatives, compounds 3 and 4 with good liposolubility showed significantly potent activity than crocetin (1) against hypoxia-induced cytotoxicity. Further mechanisms studies indicated that the cardioprotective effect of compounds 3 and 4 was due to these abilities by decreasing LDH release, preserving mitochondrial viabilities and reducing oxidative stress-induced depolarization of MMP. Our results demonstrated that compounds 3 and 4 as a new class of crocetin diamide derivatives could be developed as potential agents in our further drug development studies for ischemic heart disease.

Keywords: Cardioprotective effect; Crocetin; Diamide derivatives; Synthesis.

MeSH terms

  • Animals
  • Carotenoids / chemical synthesis
  • Carotenoids / pharmacology*
  • Cell Hypoxia
  • Cell Line
  • Diamide / chemical synthesis
  • Diamide / pharmacology*
  • L-Lactate Dehydrogenase / metabolism
  • Membrane Potential, Mitochondrial / drug effects
  • Molecular Structure
  • Myocytes, Cardiac / drug effects*
  • Oxidative Stress / drug effects
  • Rats
  • Vitamin A / analogs & derivatives

Substances

  • trans-sodium crocetinate
  • Diamide
  • Vitamin A
  • Carotenoids
  • L-Lactate Dehydrogenase