Synthesis and Antibacterial Activity of Ionic Liquids and Organic Salts Based on Penicillin G and Amoxicillin hydrolysate Derivatives against Resistant Bacteria

Pharmaceutics
Ricardo FerrazLuís C Branco

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 Escherichiacoli and Staphylococcusaureus 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.

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Citations

Mar 28, 2020·Pharmaceutics·Sónia TeixeiraLuís C Branco
Sep 10, 2020·Antibiotics·Cristina PrudêncioRicardo Ferraz
Sep 27, 2020·Pharmaceutics·Miguel M Santos, Luís C Branco
Apr 4, 2021·Microorganisms·Corneliu Ovidiu VrancianuMariana Carmen Chifiriuc
May 1, 2021·International Journal of Molecular Sciences·Rita CaparicaTânia Santos de Almeida
Jun 9, 2021·Advances in Colloid and Interface Science·Zari FallahRajender S Varma

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Methods Mentioned

BETA
acylation
NMR

Software Mentioned

OSILs

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