Synthesis and Biological Evaluation of Amphotericin B Formulations Based on Organic Salts and Ionic Liquids against Leishmania infantum

Ricardo Ferraz, Nuno Santarém, Andreia F. M. Santos, Manuel L. Jacinto, Anabela Cordeiro-da-Silva, Cristina Prudêncio, João Paulo Noronha, Luis C. Branco, Zeljko Petrovski

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Abstract

Nowadays, organic salts and ionic liquids (OSILs) containing active pharmaceutical ingredients (APIs) are being explored as drug delivery systems in modern therapies (OSILs-API). In that sense, this work is focused on the development of novel OSILs-API based on amphotericin B through an innovative procedure and the evaluation of the respective biological activity against Leishmania infantum. Several ammonium, methylimidazolium, pyridinium and phosphonium organic cations combined with amphotericin B as anion were synthesized in moderate to high yields and high purities by the water-reduced buffer neutralization method. All prepared compounds were characterized to confirm the desired chemical structure and the specific optical rotation ([α]D25) was also determined. The biological assays performed on L. infantum promastigotes showed increased activity against this parasitic disease when compared with the starting chloride forms and amphotericin B alone, highlighting [P6,6,6,14][AmB] as the most promising formulation. Possible synergism in the antiprotozoal activity was also evaluated for [P6,6,6,14][AmB], since it was proven to be the compound with the highest toxicity. This work reported a simple synthetic method, which can be applied to prepare other organic salts based on molecules containing fragile chemical groups, demonstrating the potential of these OSILs-AmB as possible agents against leishmaniasis.

Original languageEnglish
Article number1841
Number of pages12
JournalAntibiotics
Volume11
Issue number12
DOIs
Publication statusPublished - 19 Dec 2022

Keywords

  • active pharmaceutical ingredients
  • amphotericin B
  • Leishmania infantum
  • leishmaniasis
  • organic salts and ionic liquids

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