Study on synthesis and bioactivity of biotinylated emodin

Appl Microbiol Biotechnol. 2017 Jul;101(13):5259-5266. doi: 10.1007/s00253-017-8243-3. Epub 2017 Apr 6.

Abstract

A novel compound biotinylated emodin was synthesized by a two-step acyl chloride method which connects the biotin to emodin with esterification reaction. The product was characterized with ultraviolet-visible spectrophotometry, fourier transform infrared and high-performance liquid chromatography tandem mass spectrometry techniques. Its antibacterial activity against Staphylococcus aureus CMCC 26003 was investigated, and the emodin- and biotinylated emodin-caused antibacterial mechanism was proposed. It was shown that the product was isolated and activity of emodin was remained. These results indicated that our study provides a kind of chemosynthesis method under mild conditions and a strong molecular tool for investigating the emodin-binding protein.

Keywords: Bioactivity; Biotinylated emodin; Chemical synthesis; Emodin; Staphylococcus aureus.

MeSH terms

  • Anthraquinones
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / metabolism*
  • Anti-Bacterial Agents / pharmacology
  • Biotinylation
  • Chromatography, Liquid
  • Emodin / chemical synthesis*
  • Emodin / chemistry
  • Emodin / metabolism*
  • Emodin / pharmacology
  • Esterification
  • Spectrophotometry, Ultraviolet
  • Staphylococcus aureus / drug effects

Substances

  • Anthraquinones
  • Anti-Bacterial Agents
  • Emodin