A convenient preparation of 6-oligo(lactic acid)cyclomaltoheptaose as kinetically degradable derivative for controlled release of amoxicillin

Carbohydr Res. 2008 Oct 13;343(15):2517-22. doi: 10.1016/j.carres.2008.06.010. Epub 2008 Jun 17.

Abstract

6-Oligo(lactic acid)cyclomaltoheptaose (6-OLA-betaCD) with an average substitution of about 7.0 lactic acid units was prepared as a new water-soluble cyclomaltoheptaose (betaCD) derivative (solubility of about 70.7-fold that of betaCD), based on the ring-opening polymerization of 3,6-dimethyl-1,4-dioxane-2,5-dione (lactide). The product was characterized by (1)H NMR, (13)C NMR, IR, and MS spectroscopy. The complexation of amoxicillin with 6-OLA-betaCD was found to be much stronger than that with betaCD at first, and then 6-OLA-betaCD was shown to decompose moderately into betaCD and lactic acid. 6-OLA-betaCD might be greatly valuable in a controlled release system for Amoxicillin (AMX).

MeSH terms

  • Amoxicillin / administration & dosage
  • Amoxicillin / pharmacokinetics*
  • Chemistry, Pharmaceutical / methods
  • Delayed-Action Preparations*
  • Dose-Response Relationship, Drug
  • Hydrolysis
  • Kinetics
  • Lactic Acid / chemistry*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry / methods
  • Models, Chemical
  • Solubility
  • Spectrometry, Mass, Electrospray Ionization / methods
  • Spectrophotometry, Infrared / methods
  • Ultraviolet Rays
  • beta-Cyclodextrins / chemistry*

Substances

  • Delayed-Action Preparations
  • beta-Cyclodextrins
  • Lactic Acid
  • Amoxicillin
  • betadex