Design, synthesis, and activity evaluation of water-soluble propofol derivatives as anesthetic drugs

Bioorg Med Chem Lett. 2024 Nov 15:113:129972. doi: 10.1016/j.bmcl.2024.129972. Epub 2024 Sep 21.

Abstract

In this work, two series of water-soluble derivatives were designed and synthesized based on the structure of propofol as the lead compound. Furthermore, the anesthetic activities of the synthesized compounds were evaluated in vivo against mice, and the in vitro propofol release rate from five target compounds was determined. The findings of this study have shown that series II compounds which possess the structure feature of propofol + γ-hydroxybutyric acid + α-aminoacetate or γ-aminobutyrate have higher therapeutic index than that of series I compounds which possess the structure feature of propofol + α-aminoacetate or β-aminopropionate. In addition, the rate of propofol released from series II compounds was significantly better than that of series I compounds. Among series II compounds, compound II-20 had a therapeutic index of 5.6 (propofol = 2.7), a duration time of 571 s (propofol = 57 s), and no significant toxicity was observed in vivo, which made it valuable for further development.

Keywords: Anesthetic activity; Duration time; Propofol; Therapeutic index; Water-soluble derivatives.

MeSH terms

  • Aminobutyrates / chemical synthesis
  • Aminobutyrates / chemistry
  • Aminobutyrates / pharmacology
  • Anesthetics / chemical synthesis
  • Anesthetics / chemistry
  • Anesthetics / pharmacology
  • Anesthetics, Intravenous / chemical synthesis
  • Anesthetics, Intravenous / chemistry
  • Anesthetics, Intravenous / pharmacology
  • Animals
  • Dose-Response Relationship, Drug
  • Drug Design*
  • Mice
  • Molecular Structure
  • Propofol* / chemical synthesis
  • Propofol* / chemistry
  • Propofol* / pharmacology
  • Solubility*
  • Structure-Activity Relationship
  • Water* / chemistry

Substances

  • Anesthetics
  • Anesthetics, Intravenous
  • Propofol
  • Water
  • Aminobutyrates