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Open AccessArticle

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

1
Ciências Químicas e das Biomoléculas (CQB) e Centro de Investigação em Saúde e Ambiente (CISA), Escola Superior de Saúde do Instituto Politécnico do Porto, 4400-330 Porto, Portugal
2
LAQV-REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre 687, 4169-007 Porto, Portugal
3
LAQV-REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia da Universidade Nova de Lisboa, 2829-516 Caparica, Portugal
4
i3S, Instituto de Inovação e Investigação em Saúde, Universidade do Porto, 4099-002 Porto, Portugal
*
Authors to whom correspondence should be addressed.
These two authors contribute equally to this work.
Pharmaceutics 2020, 12(3), 221; https://doi.org/10.3390/pharmaceutics12030221 (registering DOI)
Received: 31 December 2019 / Revised: 19 February 2020 / Accepted: 19 February 2020 / Published: 2 March 2020
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. View Full-Text
Keywords: active pharmaceutical ingredients-ionic liquids and organic salts (API-OSILs); penicillin G and amoxicillin hydrolysate derivatives; sensitive bacteria; resistant bacteria active pharmaceutical ingredients-ionic liquids and organic salts (API-OSILs); penicillin G and amoxicillin hydrolysate derivatives; sensitive bacteria; resistant bacteria
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Ferraz, R.; Silva, D.; Dias, A.R.; Dias, V.; Santos, M.M.; Pinheiro, L.; Prudêncio, C.; Noronha, J.P.; Petrovski, Ž.; Branco, L.C. Synthesis and Antibacterial Activity of Ionic Liquids and Organic Salts Based on Penicillin G and Amoxicillin hydrolysate Derivatives against Resistant Bacteria. Pharmaceutics 2020, 12, 221.

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