Quantitative Structure-Cytotoxicity Relationship of Chalcones

Anticancer Res. 2017 Mar;37(3):1091-1098. doi: 10.21873/anticanres.11421.

Abstract

Background: Fifteen chalcones were subjected to quantitative structure-activity relationship (QSAR) analysis based on their cytotoxicity and tumor specificity, in order to find their new biological activities.

Materials and methods: Cytotoxicity against four human oral squamous cell carcinoma cell lines and three oral mesenchymal cells was determined by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. Tumor specificity (TS) was evaluated by the ratio of the mean 50% cytotoxic concentration (CC50) against normal cells to that against tumor cell lines. Potency-selectivity expression (PSE) value was calculated by dividing TS by CC50 against tumor cells. Apoptosis markers were detected by western blot analysis. Physicochemical, structural and quantum-chemical parameters were calculated based on the conformations optimized by force-field minimization.

Results: Among 15 chalcone derivatives, (2E)-1-(2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one had the highest TS and PSE values, comparable with those of doxorubicin and methotrexate, respectively. This compound also stimulated the cleavage of poly(ADP-ribose) polymerase and caspase-3. Chalone TS values were correlated with molecular shape and polarization rather than the types of substituted groups. None of the compounds had any anti-HIV activity.

Conclusion: Chemical modification of the lead compound may be a potential choice for designing new types of anticancer drugs.

Keywords: Chalcones; QSAR analysis; anti-HIV activity; apoptosis induction; cytotoxicity; tumor selectivity.

MeSH terms

  • Anti-HIV Agents / chemistry
  • Antineoplastic Agents / chemistry*
  • Apoptosis
  • Carcinoma, Squamous Cell / drug therapy
  • Cell Line, Tumor
  • Chalcones / chemistry*
  • Child
  • Doxorubicin / chemistry
  • Drug Screening Assays, Antitumor
  • Epithelial Cells / drug effects
  • Female
  • Hep G2 Cells
  • Humans
  • Mesoderm / cytology
  • Methotrexate / chemistry
  • Mouth Neoplasms / drug therapy
  • Quantitative Structure-Activity Relationship

Substances

  • Anti-HIV Agents
  • Antineoplastic Agents
  • Chalcones
  • Doxorubicin
  • Methotrexate