Fluoroquinolone-Based Organic Salts and Ionic Liquids as Highly Bioavailable Broad-Spectrum Antimicrobials

Diogo Madeira; Celso Alves; Joana Silva; Catarina Florindo; Alexandra Costa; Željko Petrovski; Isabel M. Marrucho; Rui Pedrosa; Miguel M. Santos; Luís C. Branco

doi:10.3390/IECP2020-08649

Fluoroquinolone-Based Organic Salts and Ionic Liquids as Highly Bioavailable Broad-Spectrum Antimicrobials

Diogo Madeira, Celso Alves, Joana Silva, Catarina Florindo, Alexandra Costa, Željko Petrovski, Isabel M. Marrucho, Rui Pedrosa, Miguel M. Santos, Luís C. Branco

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Abstract

The majority of antibiotics display low oral bioavailability due to reduced solubility in water and/or inefficient permeability across biological membranes. Their efficiency is further limited by the frequent presence of polymorphic structures with different pharmaceutical activities. In this communication, we present our latest results on the development of organic salts and ionic liquids from fluoroquinolones (FQ-OSILs) as highly efficient ionic formulations of this family of antimicrobials. Ciprofloxacin and norfloxacin were used as anions and as cations, by combination with biocompatible organic counter-ions. In vitro bioavailability studies showed that all prepared FQ-OSILs presented higher solubility in water than the original drugs. All compounds were found to be isomorphic and with tailorable antimicrobial activity according to the cation–anion combination against Staphylococcus aureus, Bacillus subtilis and Klebsiella pneumoniae strains.

Original language	English
Article number	3
Journal	Proceedings
Volume	78
Issue number	1
DOIs	https://doi.org/10.3390/IECP2020-08649
Publication status	Published - 2021
Event	1st International Electronic Conference on Pharmaceutics, IECP 2020 - Virtual, Online Duration: 1 Dec 2020 → 15 Dec 2020

Keywords

active pharmaceutical ingredients as organic salts and ionic liquids (API–OSILs)
antibiotics
ciprofloxacin
fluoroquinolones
ionic liquids
norfloxacin
polymorphism

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proceedings-78-00003Final published version, 311 KBLicence: CC BY

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@article{b0ada1f10dfa420e80c6bfa1ce819932,

title = "Fluoroquinolone-Based Organic Salts and Ionic Liquids as Highly Bioavailable Broad-Spectrum Antimicrobials",

abstract = "The majority of antibiotics display low oral bioavailability due to reduced solubility in water and/or inefficient permeability across biological membranes. Their efficiency is further limited by the frequent presence of polymorphic structures with different pharmaceutical activities. In this communication, we present our latest results on the development of organic salts and ionic liquids from fluoroquinolones (FQ-OSILs) as highly efficient ionic formulations of this family of antimicrobials. Ciprofloxacin and norfloxacin were used as anions and as cations, by combination with biocompatible organic counter-ions. In vitro bioavailability studies showed that all prepared FQ-OSILs presented higher solubility in water than the original drugs. All compounds were found to be isomorphic and with tailorable antimicrobial activity according to the cation–anion combination against Staphylococcus aureus, Bacillus subtilis and Klebsiella pneumoniae strains.",

keywords = "active pharmaceutical ingredients as organic salts and ionic liquids (API–OSILs), antibiotics, ciprofloxacin, fluoroquinolones, ionic liquids, norfloxacin, polymorphism",

author = "Diogo Madeira and Celso Alves and Joana Silva and Catarina Florindo and Alexandra Costa and {\v Z}eljko Petrovski and Marrucho, {Isabel M.} and Rui Pedrosa and Santos, {Miguel M.} and Branco, {Lu{\'i}s C.}",

note = "This work was supported by the Associate Laboratory for Green Chemistry LAQV and Centro de Qu{\'i}mica Estrutural which are financed by national funds from FCT/MCTES (UIDB/50006/2020 and UID/QUI/00100/2013, respectively). The authors also thank Funda{\c c}{\~a}o para a Ci{\^e}ncia e Tecnologia for the projects PTDC/QUI-QOR/32406/2017, PEst-C/LA0006/2013, and RECI/BBBBQB/0230/2012, as well as one contract under Investigador FCT (L. C. Branco). ; 1st International Electronic Conference on Pharmaceutics, IECP 2020 ; Conference date: 01-12-2020 Through 15-12-2020",

year = "2021",

doi = "10.3390/IECP2020-08649",

language = "English",

volume = "78",

journal = "Proceedings",

issn = "2504-3900",

publisher = "MDPI - Multidisciplinary Digital Publishing Institute",

number = "1",

}

TY - JOUR

T1 - Fluoroquinolone-Based Organic Salts and Ionic Liquids as Highly Bioavailable Broad-Spectrum Antimicrobials

AU - Madeira, Diogo

AU - Alves, Celso

AU - Silva, Joana

AU - Florindo, Catarina

AU - Costa, Alexandra

AU - Petrovski, Željko

AU - Marrucho, Isabel M.

AU - Pedrosa, Rui

AU - Santos, Miguel M.

AU - Branco, Luís C.

N1 - This work was supported by the Associate Laboratory for Green Chemistry LAQV and Centro de Química Estrutural which are financed by national funds from FCT/MCTES (UIDB/50006/2020 and UID/QUI/00100/2013, respectively). The authors also thank Fundação para a Ciência e Tecnologia for the projects PTDC/QUI-QOR/32406/2017, PEst-C/LA0006/2013, and RECI/BBBBQB/0230/2012, as well as one contract under Investigador FCT (L. C. Branco).

PY - 2021

Y1 - 2021

N2 - The majority of antibiotics display low oral bioavailability due to reduced solubility in water and/or inefficient permeability across biological membranes. Their efficiency is further limited by the frequent presence of polymorphic structures with different pharmaceutical activities. In this communication, we present our latest results on the development of organic salts and ionic liquids from fluoroquinolones (FQ-OSILs) as highly efficient ionic formulations of this family of antimicrobials. Ciprofloxacin and norfloxacin were used as anions and as cations, by combination with biocompatible organic counter-ions. In vitro bioavailability studies showed that all prepared FQ-OSILs presented higher solubility in water than the original drugs. All compounds were found to be isomorphic and with tailorable antimicrobial activity according to the cation–anion combination against Staphylococcus aureus, Bacillus subtilis and Klebsiella pneumoniae strains.

AB - The majority of antibiotics display low oral bioavailability due to reduced solubility in water and/or inefficient permeability across biological membranes. Their efficiency is further limited by the frequent presence of polymorphic structures with different pharmaceutical activities. In this communication, we present our latest results on the development of organic salts and ionic liquids from fluoroquinolones (FQ-OSILs) as highly efficient ionic formulations of this family of antimicrobials. Ciprofloxacin and norfloxacin were used as anions and as cations, by combination with biocompatible organic counter-ions. In vitro bioavailability studies showed that all prepared FQ-OSILs presented higher solubility in water than the original drugs. All compounds were found to be isomorphic and with tailorable antimicrobial activity according to the cation–anion combination against Staphylococcus aureus, Bacillus subtilis and Klebsiella pneumoniae strains.

KW - active pharmaceutical ingredients as organic salts and ionic liquids (API–OSILs)

KW - antibiotics

KW - ciprofloxacin

KW - fluoroquinolones

KW - ionic liquids

KW - norfloxacin

KW - polymorphism

U2 - 10.3390/IECP2020-08649

DO - 10.3390/IECP2020-08649

M3 - Conference article

SN - 2504-3900

VL - 78

JO - Proceedings

JF - Proceedings

IS - 1

M1 - 3

T2 - 1st International Electronic Conference on Pharmaceutics, IECP 2020

Y2 - 1 December 2020 through 15 December 2020

ER -

Fluoroquinolone-Based Organic Salts and Ionic Liquids as Highly Bioavailable Broad-Spectrum Antimicrobials

Abstract

Keywords

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