Utility of poly(ethylene glycol) conjugation to create prodrugs of amphotericin B

Bioconjug Chem. 2003 May-Jun;14(3):661-6. doi: 10.1021/bc0256594.

Abstract

This paper reports on the synthesis, safety, and efficacy of a series of water-soluble derivatives of poly(ethylene glycol) (PEG)-conjugated amphotericin B (AmB). PEG 40 000 attached to the sugar amino group of AmB via labile carbamate and carbonate linkages was examined. The synthetic program conducted for this investigation provided a series of disubstituted PEG-AmB derivatives which had in vitro PEG half-life of hydrolyses rates in rat plasma varying between 1 and 3 h. Importantly, all conjugates demonstrated less than 6% hydrolysis following 24 h incubation in pH 7.4 phosphate buffer at 25 degrees C and showed solubilities greater than 46 mg/mL in aqueous solutions. The solubility of AmB in the conjugates increased up to approximately 200 times compared to unmodified AmB in saline. As a major finding, this investigation demonstrated that conjugation of PEG to AmB could produce conjugates that were significantly (6x) less toxic than AmB-deoxycholate and maintained, or even had enhanced, in vivo antifungal activity.

MeSH terms

  • Amphotericin B / administration & dosage
  • Amphotericin B / chemical synthesis
  • Amphotericin B / metabolism*
  • Animals
  • Female
  • Male
  • Mice
  • Mice, Inbred ICR
  • Polyethylene Glycols / administration & dosage
  • Polyethylene Glycols / chemical synthesis
  • Polyethylene Glycols / metabolism*
  • Prodrugs / administration & dosage
  • Prodrugs / chemical synthesis
  • Prodrugs / metabolism*
  • Rabbits
  • Rats
  • Rats, Sprague-Dawley

Substances

  • Prodrugs
  • Polyethylene Glycols
  • Amphotericin B