Synthesis and antibacterial activity of ionic liquids and organic salts based on penicillin g and amoxicillin hydrolysate derivatives against resistant bacteria

Ricardo Ferraz, Dário Silva, Ana Rita Dias, Vitorino Dias, Miguel M. Santos, Luís Pinheiro, Cristina Prudêncio, João Paulo Noronha, Željko Petrovski, Luís C. Branco

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6 Citations (Scopus)
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Abstract

The preparation and characterization of ionic liquids and organic salts (OSILs) that contain anionic penicillin G [secoPen] and amoxicillin [seco-Amx] hydrolysate derivatives and their in vitro antibacterial activity against sensitive and resistant Escherichia coli and Staphylococcus aureus strains is reported. Eleven hydrolyzed β-lactam-OSILs were obtained after precipitation in moderate-to-high yields via the neutralization of the basic ammonia buffer of antibiotics with different cation hydroxide salts. The obtained minimum inhibitory concentration (MIC) data of the prepared compounds showed a relative decrease of the inhibitory concentrations (RDIC) in the order of 100 in the case of [C2OHMIM][seco-Pen] against sensitive S. aureus ATCC25923 and, most strikingly, higher than 1000 with [C16Pyr][seco-Amx] against methicillin-resistant Staphylococcus aureus (MRSA) ATCC 43300. These outstanding in vitro results showcase that a straightforward transformation of standard antibiotics into hydrolyzed organic salts can dramatically change the pharmaceutical activity of a drug, including giving rise to potent formulations of antibiotics against deadly bacteria strains.

Original languageEnglish
Article number221
JournalPharmaceutics
Volume12
Issue number3
DOIs
Publication statusPublished - Mar 2020

Keywords

  • Active pharmaceutical ingredients-ionic liquids and organic salts (API-OSILs)
  • Penicillin G and amoxicillin hydrolysate derivatives
  • Resistant bacteria
  • Sensitive bacteria

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