Host-guest inclusion system of norathyriol with β-cyclodextrin and its derivatives: preparation, characterization, and anticancer activity

J Biosci Bioeng. 2014 Jun;117(6):775-9. doi: 10.1016/j.jbiosc.2013.12.001. Epub 2014 Feb 6.

Abstract

The characterization, binding ability and inclusion complexation behavior of the inclusion complexes of norathyriol with β-cyclodextrin (β-CD) and its derivatives such as hydroxypropyl-β-cyclodextrin (HPβCD), sulfobutyl ether β-cyclodextrin (SBEβCD) and mono (6-ethylene-diamino-6-deoxy)-β-cyclodextrin (ENβCD) were investigated in both solution and solid state by means of femtosecond spectroscopy, (1)H and 2D nuclear magnetic resonance, powder X-ray diffraction. The results showed that the aqueous solubility of the complexes was much higher than that of norathyriol. The cytotoxicity of complexes on human colon cancer cell lines HT-29, SW480, Lovo and HCT116 indicated that the antitumor activities of the complexes were better than that of norathyriol. This high antitumor activity, along with the satisfactory aqueous solubility of the complexes, will be potentially useful for their application on cancer chemotherapies.

Keywords: Anticancer activity; Binding ability; Characterization; Inclusion complex; Norathyriol; β-Cyclodextrin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2-Hydroxypropyl-beta-cyclodextrin
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology
  • Cell Proliferation / drug effects
  • Drug Screening Assays, Antitumor
  • Ethylenediamines / chemical synthesis*
  • Ethylenediamines / pharmacology
  • HCT116 Cells
  • HT29 Cells
  • Humans
  • Inhibitory Concentration 50
  • Powder Diffraction
  • Solubility
  • X-Ray Diffraction
  • beta-Cyclodextrins / chemical synthesis*
  • beta-Cyclodextrins / chemistry*
  • beta-Cyclodextrins / pharmacology

Substances

  • Antineoplastic Agents
  • Ethylenediamines
  • beta-Cyclodextrins
  • ethylene-diamine-beta-cyclodextrin
  • 2-Hydroxypropyl-beta-cyclodextrin
  • SBE4-beta-cyclodextrin