Antimicrobial Activities of Highly Bioavailable Organic Salts and Ionic Liquids from Fluoroquinolones

• Type: Article in International Scientific Journal
• Date: 2020

Authors

Santos, MM (Author) FCUP; Alves, C (Author) Other; Silva, J (Author) Other; Florindo, C (Author) Other; Costa, A (Author) Other; Petrovski, Z (Author) Other; Marrucho, IM (Author) Other; Pedrosa, R (Author) Other; Branco, LC (Author) Other

Journal

Title: Pharmaceutics

Vol. 12

Pages: 1-15

ISSN: 1999-4923

Publisher: MDPI

Indexing

ISI Web of Knowledge - 33 Citations

Scopus - 35 Citations

Other information

Authenticus ID: P-00S-J2W

DOI: 10.3390/pharmaceutics12080694

Abstract (EN): As the development of novel antibiotics has been at a halt for several decades, chemically enhancing existing drugs is a very promising approach to drug development. Herein, we report the preparation of twelve organic salts and ionic liquids (OSILs) from ciprofloxacin and norfloxacin as anions with enhanced antimicrobial activity. Each one of the fluoroquinolones (FQs) was combined with six different organic hydroxide cations in 93-100% yield through a buffer-assisted neutralization methodology. Six of those were isomorphous salts while the remaining six were ionic liquids, with four of them being room temperature ionic liquids. The prepared compounds were not toxic to healthy cell lines and displayed between 47- and 1416-fold more solubility in water at 25 and 37 degrees C than the original drugs, with the exception of the ones containing the cetylpyridinium cation. In general, the antimicrobial activity againstKlebsiella pneumoniaewas particularly enhanced for the ciprofloxacin-based OSILs, with up to ca. 20-fold decreases of the inhibitory concentrations in relation to the parent drug, while activity againstStaphylococcus aureusand the commensalBacillus subtilisstrain was often reduced. Depending on the cation-drug combination, broad-spectrum or strain-specific antibiotic salts were achieved, potentially leading to the future development of highly bioavailable and safe antimicrobial ionic formulations.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 15