Design, synthesis and biological evaluation of cinnamic acid derivatives with synergetic neuroprotection and angiogenesis effect

Eur J Med Chem. 2019 Dec 1:183:111695. doi: 10.1016/j.ejmech.2019.111695. Epub 2019 Sep 13.

Abstract

As for complex brain diseases involved with multiple pathogenic factors, it is extremely difficult to achieve curative effect by acting on a single target. Multi-approach drugs provide a promising prospect in the treatment of complex brain diseases and have been attracting more and more interest. Enlightened by synergetic effect of combination in traditional herb medicines, forty-two novel cinnamic acid derivatives were designed and synthesized by introducing capsaicin and/or ligustrazine moieties to enhance biological activities in both neurological function and neurovascular protection. Elevated levels of cell viability on human brain microvascular endothelium cell line (HBMEC-2) and human neuroblastoma cell line (SH-SY5Y) against free radical injury were observed in most of compounds. Among them, compound 14a exhibited the most potent activities with a significant EC50 value of 3.26 ± 0.16 μM (HBMEC-2) and 2.41 ± 0.10 μM (SH-SY5Y). Subsequently, the results of morphological staining and flow cytometry analysis experiments on both cell lines showed that 14a had the potential to block apoptosis, maintain cell morphological integrity and protect physiological function of mitochondria. Moreover, 14a displayed specific angiogenesis effect in the chick chorioallantoic membrane (CAM) assay; and the results of RT-PCR suggested that the mechanism for angiogenesis effect was associated with the enhancement of the expressions of VEGFR2 mRNA in chick embryo. Preliminary structure-activity relationship was analyzed. The above evidences suggested that conjunctures gained by combining active ingredients in traditional herb medicines deserved further study and might provide references in discovering dual-effective lead compounds for brain diseases.

Keywords: Angiogenesis; Brain injury; Cinnamic acids; Dual effects; Neuroprotective.

MeSH terms

  • Angiogenesis Inducing Agents / chemical synthesis
  • Angiogenesis Inducing Agents / chemistry
  • Angiogenesis Inducing Agents / pharmacology*
  • Apoptosis / drug effects
  • Capsaicin / chemistry
  • Capsaicin / pharmacology
  • Cell Line
  • Cell Survival / drug effects
  • Cinnamates / chemical synthesis
  • Cinnamates / chemistry
  • Cinnamates / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Design*
  • Humans
  • Membrane Potential, Mitochondrial / drug effects
  • Molecular Structure
  • Neuroprotective Agents / chemical synthesis
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / pharmacology*
  • Oxidative Stress / drug effects
  • Pyrazines / chemistry
  • Pyrazines / pharmacology
  • RNA, Messenger / antagonists & inhibitors
  • RNA, Messenger / genetics
  • RNA, Messenger / metabolism
  • Structure-Activity Relationship
  • Vascular Endothelial Growth Factor Receptor-2 / antagonists & inhibitors
  • Vascular Endothelial Growth Factor Receptor-2 / genetics
  • Vascular Endothelial Growth Factor Receptor-2 / metabolism

Substances

  • Angiogenesis Inducing Agents
  • Cinnamates
  • Neuroprotective Agents
  • Pyrazines
  • RNA, Messenger
  • cinnamic acid
  • KDR protein, human
  • Vascular Endothelial Growth Factor Receptor-2
  • Capsaicin
  • tetramethylpyrazine