Efficient Photodynamic Killing of Gram-Positive Bacteria by Synthetic Curcuminoids

Int J Mol Sci. 2020 Nov 27;21(23):9024. doi: 10.3390/ijms21239024.

Abstract

In our previous study, we have demonstrated that curcumin can efficiently kill the anaerobic bacterium Propionibacterium acnes by irradiation with low-dose blue light. The curcuminoids present in natural plant turmeric mainly include curcumin, demethoxycurcumin, and bisdemethoxycurcumin. However, only curcumin is commercially available. Eighteen different curcumin analogs, including demethoxycurcumin and bisdemethoxycurcumin, were synthesized in this study. Their antibacterial activity against Gram-positive aerobic bacteria Staphylococcus aureus and Staphylococcus epidermidis was investigated using the photodynamic inactivation method. Among the three compounds in turmeric, curcumin activity is the weakest, and bisdemethoxycurcumin possesses the strongest activity. However, two synthetic compounds, (1E,6E)-1,7-bis(5-methylthiophen-2-yl)hepta-1,6-diene-3,5-dione and (1E,6E)-1,7-di(thiophen-2-yl)hepta-1,6-diene-3,5-dione, possess the best antibacterial activity among all compounds examined in this study. Their chemical stability is also better than that of bisdemethoxycurcumin, and thus has potential for future clinical applications.

Keywords: Staphylococcus aureus; Staphylococcus epidermis; bisdemethoxycurcumin; curcumin; curcuminoid; demethoxycurcumin; photodynamic inactivation.

MeSH terms

  • Cell Membrane / drug effects
  • Cell Membrane / radiation effects
  • Cell Membrane / ultrastructure
  • Diarylheptanoids / chemical synthesis
  • Diarylheptanoids / chemistry
  • Diarylheptanoids / pharmacology*
  • Gram-Positive Bacteria / drug effects*
  • Gram-Positive Bacteria / radiation effects
  • Gram-Positive Bacteria / ultrastructure
  • Light
  • Microbial Sensitivity Tests
  • Microbial Viability / drug effects*
  • Photochemotherapy*

Substances

  • Diarylheptanoids