Supramolecular interaction of methotrexate with cucurbit[7]uril and analytical application

Spectrochim Acta A Mol Biomol Spectrosc. 2017 Aug 5:183:131-137. doi: 10.1016/j.saa.2017.04.060. Epub 2017 Apr 20.

Abstract

The supramolecular interaction between cucurbit[7]uril (CB[7]) as the host and the anti-cancer drug methotrexate (MTX) as the guest was studied using fluorescence spectroscopy, UV-visible absorption spectroscopy, 1H NMR, 2D NOESY, and theoretical calculations. The experimental results confirmed the formation of 1:2 inclusion complex with CB[7] and indicated a simple and sensitive competitive method for the fluorescence detection of MTX. It was found that the fluorescence intensities of CB[7]-palmatine, CB[7]-berberine and CB[7]-coptisine were quenched linearly upon the addition of MTX. The linear ranges obtained in the detection of MTX were 0.1-15μgmL-1, 0.2-15μgmL-1, and 0.4-15μgmL-1 with detection limits of 0.03μgmL-1, 0.06μgmL-1, and 0.13μgmL-1, respectively. This method can be used for the determination of MTX in biological fluids. These results suggested that cucurbit[7]uril is a promising drug carrier for targeted MTX delivery and monitoring, with improved efficacy and reduced toxicity in normal tissues.

Keywords: Cucurbit[7]uril; Fluorescence spectroscopy; Inclusion complex; Methotrexate.

MeSH terms

  • Bridged-Ring Compounds / chemistry
  • Bridged-Ring Compounds / metabolism*
  • Drug Carriers / chemistry
  • Drug Carriers / metabolism
  • Imidazoles / chemistry
  • Imidazoles / metabolism*
  • Limit of Detection
  • Linear Models
  • Methotrexate / analysis*
  • Methotrexate / chemistry
  • Methotrexate / metabolism*
  • Spectrometry, Fluorescence

Substances

  • Bridged-Ring Compounds
  • Drug Carriers
  • Imidazoles
  • cucurbit(7)uril
  • Methotrexate