Ultrasound-assisted biosynthesis of novel methotrexate-conjugates

Ultrason Sonochem. 2018 Nov:48:51-56. doi: 10.1016/j.ultsonch.2018.05.017. Epub 2018 May 17.

Abstract

New methotrexate-acylglycerols and methotrexate-cyclodextrins (α, β and γ-CD) conjugates were obtained via esterification or transesterification reactions. All reactions were catalysed by esterases namely immobilized Lipase from Candida antarctica B and Lipase from Thermomyces lanuginosus. The use of ultrasound to assist the reactions revealed to be a key factor to obtain high conversion yields on both MTX conjugates. Transesterification reactions including long chain triacylglycerols were only successful when ultrasound was applied. In cyclodextrins esterification a higher number of MTX molecules was also linked to cyclodextrins when ultrasound was used. All the conjugates were characterized by MALDI-TOF and NMR spectroscopy.

Keywords: Biosynthesis; Cyclodextrins; Lipases; Methotrexate; Triacylglycerols; Ultrasound.

MeSH terms

  • Antimetabolites, Antineoplastic / chemistry*
  • Cyclodextrins / chemistry*
  • Enzymes, Immobilized / chemistry
  • Esterification
  • Glycerol / chemistry*
  • Lipase / chemistry
  • Methotrexate / chemistry*
  • Proton Magnetic Resonance Spectroscopy
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Ultrasonic Waves*

Substances

  • Antimetabolites, Antineoplastic
  • Cyclodextrins
  • Enzymes, Immobilized
  • Lipase
  • Glycerol
  • Methotrexate