Cytotoxic and glycosaminoglycan priming activities of novel 4-anilinequinazoline β-D-xylosides

Carbohydr Res. 2018 Jun 30:463:6-13. doi: 10.1016/j.carres.2018.04.007. Epub 2018 Apr 13.

Abstract

β-D-xylosides with cytotoxic aglycones have augmented cytotoxicity towards animal cells because β-D-xyloside-primed glycosaminoglycans further enhance the aglycone's cytotoxicity. In this study, we designed and synthesized different 4-anilinequinazoline β-D-xylosides and found that compounds 7-10 possessing 3-chloro-4-((3-fluorobenzyl)oxy)aniline group as in anticancer drug lapatinib also primed glycosaminoglycans and were highly cytotoxic to cancer cells.

Keywords: 4-Anilinequinazolines; Cytotoxicity; Glycosaminoglycans; β-D-xylosides.

MeSH terms

  • A549 Cells
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Glycosaminoglycans / chemistry*
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Glycosides / pharmacology
  • HCT116 Cells
  • Humans
  • Lapatinib
  • Molecular Structure
  • Quinazolines / chemistry
  • Quinazolines / pharmacology

Substances

  • Antineoplastic Agents
  • Glycosaminoglycans
  • Glycosides
  • Quinazolines
  • xylosides
  • Lapatinib