Application of TLC to Evaluate the Lipophilicity of Newly Synthesized Betulin Derivatives

J Chromatogr Sci. 2020 Apr 23;58(4):323-333. doi: 10.1093/chromsci/bmz117.

Abstract

Designing a new drug has recently become a very important topic that many researches are concerned with. This work relates to a newly synthesized betulin and betulone derivatives which have anticancer activity. Thin-layer chromatography was applied to evaluate the lipophilicity of these triterpenes in order to find the correlation between theoretically and experimentally calculated values of lipophilicity and the structure of compounds investigated. Moreover, the relationships between lipophilicity and pharmacokinetic parameters or anticancer activity were carried out. The similarity analysis was also done for the purpose to divide the compounds investigated into groups pointing which of these can meet the criteria for medicine substances. The cluster analysis showed the differences in the compounds grouping in relation which the values of lipophilicity are considered, i.e., calculated by computer software or obtained experimentally by use of TLC. Analysis clearly shows that those theoretically calculated values of lipophilicity are strongly connected to the structure of the compounds.

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Chromatography, Thin Layer / methods*
  • Chromatography, Thin Layer / statistics & numerical data
  • Cluster Analysis
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • Humans
  • Quantitative Structure-Activity Relationship
  • Software
  • Triterpenes / chemistry*
  • Triterpenes / pharmacology*

Substances

  • Antineoplastic Agents
  • Triterpenes
  • betulin