Enhancement of water solubility of poorly water-soluble drugs by new biocompatible N-acetyl amino acid N-alkyl cholinium-based ionic liquids

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Abstract

The major challenge of the pharmaceutical industry is to find potential solvents for poorly water-soluble drug molecules. Ionic liquids (ILs) have attracted this industry as (co-) solvents due to their unique physicochemical and biological properties. Herein, a straightforward approach for the enhancement of water solubility of paracetamol and sodium diclofenac is presented, using new biocompatible N-acetyl amino acid N-alkyl cholinium-based ionic liquids as co-solvents (0.2 - 1 mol%). These new ionic liquids were able to increase water solubility of these drugs up to four times higher than in pure water or in an inorganic salt solution. In the presence of these ILs the drugs lipophilicity (log Kow) was not significantly changed for paracetamol, but for sodium diclofenac it was possible to decrease significantly its lipophilicity. Concerning cytotoxicity in human dermal fibroblasts it was observed that ILs did not show a significant toxicity, and were able to improve cell viability compared with the respective precursors.

Original languageEnglish
Pages (from-to)227–232
JournalEuropean Journal of Pharmaceutics and Biopharmaceutics
Volume137
DOIs
Publication statusPublished - 2019

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Ionic Liquids
Solubility
Amino Acids
Water
Pharmaceutical Preparations
Diclofenac
Acetaminophen
Drug Industry
Cell Survival
Industry
Fibroblasts
Salts
Skin

Cite this

@article{7d071732acbb453bb2ee2a2848bc2790,
title = "Enhancement of water solubility of poorly water-soluble drugs by new biocompatible N-acetyl amino acid N-alkyl cholinium-based ionic liquids",
abstract = "The major challenge of the pharmaceutical industry is to find potential solvents for poorly water-soluble drug molecules. Ionic liquids (ILs) have attracted this industry as (co-) solvents due to their unique physicochemical and biological properties. Herein, a straightforward approach for the enhancement of water solubility of paracetamol and sodium diclofenac is presented, using new biocompatible N-acetyl amino acid N-alkyl cholinium-based ionic liquids as co-solvents (0.2 - 1 mol{\%}). These new ionic liquids were able to increase water solubility of these drugs up to four times higher than in pure water or in an inorganic salt solution. In the presence of these ILs the drugs lipophilicity (log Kow) was not significantly changed for paracetamol, but for sodium diclofenac it was possible to decrease significantly its lipophilicity. Concerning cytotoxicity in human dermal fibroblasts it was observed that ILs did not show a significant toxicity, and were able to improve cell viability compared with the respective precursors.",
author = "Jesus, {Ana R.} and Soromenho, {M{\'a}rio R. C.} and Raposo, {Lu{\'i}s R.} and Esperan{\cc}a, {Jos{\'e} M. S. S.} and Baptista, {Pedro V.} and Fernandes, {Alexandra R.} and Reis, {Patr{\'i}cia M.}",
note = "Copyright {\circledC} 2019. Published by Elsevier B.V.",
year = "2019",
doi = "10.1016/j.ejpb.2019.03.004",
language = "English",
volume = "137",
pages = "227–232",
journal = "European Journal of Pharmaceutics and Biopharmaceutics",
issn = "0939-6411",
publisher = "Elsevier Science B.V., Amsterdam.",

}

TY - JOUR

T1 - Enhancement of water solubility of poorly water-soluble drugs by new biocompatible N-acetyl amino acid N-alkyl cholinium-based ionic liquids

AU - Jesus, Ana R.

AU - Soromenho, Mário R. C.

AU - Raposo, Luís R.

AU - Esperança, José M. S. S.

AU - Baptista, Pedro V.

AU - Fernandes, Alexandra R.

AU - Reis, Patrícia M.

N1 - Copyright © 2019. Published by Elsevier B.V.

PY - 2019

Y1 - 2019

N2 - The major challenge of the pharmaceutical industry is to find potential solvents for poorly water-soluble drug molecules. Ionic liquids (ILs) have attracted this industry as (co-) solvents due to their unique physicochemical and biological properties. Herein, a straightforward approach for the enhancement of water solubility of paracetamol and sodium diclofenac is presented, using new biocompatible N-acetyl amino acid N-alkyl cholinium-based ionic liquids as co-solvents (0.2 - 1 mol%). These new ionic liquids were able to increase water solubility of these drugs up to four times higher than in pure water or in an inorganic salt solution. In the presence of these ILs the drugs lipophilicity (log Kow) was not significantly changed for paracetamol, but for sodium diclofenac it was possible to decrease significantly its lipophilicity. Concerning cytotoxicity in human dermal fibroblasts it was observed that ILs did not show a significant toxicity, and were able to improve cell viability compared with the respective precursors.

AB - The major challenge of the pharmaceutical industry is to find potential solvents for poorly water-soluble drug molecules. Ionic liquids (ILs) have attracted this industry as (co-) solvents due to their unique physicochemical and biological properties. Herein, a straightforward approach for the enhancement of water solubility of paracetamol and sodium diclofenac is presented, using new biocompatible N-acetyl amino acid N-alkyl cholinium-based ionic liquids as co-solvents (0.2 - 1 mol%). These new ionic liquids were able to increase water solubility of these drugs up to four times higher than in pure water or in an inorganic salt solution. In the presence of these ILs the drugs lipophilicity (log Kow) was not significantly changed for paracetamol, but for sodium diclofenac it was possible to decrease significantly its lipophilicity. Concerning cytotoxicity in human dermal fibroblasts it was observed that ILs did not show a significant toxicity, and were able to improve cell viability compared with the respective precursors.

U2 - 10.1016/j.ejpb.2019.03.004

DO - 10.1016/j.ejpb.2019.03.004

M3 - Article

VL - 137

SP - 227

EP - 232

JO - European Journal of Pharmaceutics and Biopharmaceutics

JF - European Journal of Pharmaceutics and Biopharmaceutics

SN - 0939-6411

ER -