Enhancement of water solubility of poorly water-soluble drugs by new biocompatible N-acetyl amino acid N-alkyl cholinium-based ionic liquids
[Display omitted] 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 appr...
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| Veröffentlicht in: | European journal of pharmaceutics and biopharmaceutics 2019-04, Vol.137, p.227-232 |
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| container_title | European journal of pharmaceutics and biopharmaceutics |
| container_volume | 137 |
| creator | Jesus, Ana R. Soromenho, Mário R.C. Raposo, Luís R. Esperança, José M.S.S. Baptista, Pedro V. Fernandes, Alexandra R. Reis, Patrícia M. |
| description | [Display omitted]
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 the 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 the water solubility of these drugs up to four times that in pure water or in an inorganic salt solution. In the presence of these ILs, the drugs lipophilicity (log P 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. |
| doi_str_mv | 10.1016/j.ejpb.2019.03.004 |
| format | Article |
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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 the 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 the water solubility of these drugs up to four times that in pure water or in an inorganic salt solution. In the presence of these ILs, the drugs lipophilicity (log P 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.</description><identifier>ISSN: 0939-6411</identifier><identifier>EISSN: 1873-3441</identifier><identifier>DOI: 10.1016/j.ejpb.2019.03.004</identifier><identifier>PMID: 30836180</identifier><language>eng</language><publisher>Netherlands: Elsevier B.V</publisher><subject>Amino acids ; Bioavailability ; Cytotoxicity ; Drug Delivery ; Ionic Liquids</subject><ispartof>European journal of pharmaceutics and biopharmaceutics, 2019-04, Vol.137, p.227-232</ispartof><rights>2019 Elsevier B.V.</rights><rights>Copyright © 2019 Elsevier B.V. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c448t-7c720cec22502d897abc765ffa79030ac10feae9937bab9de5d3d57bb25a1e613</citedby><cites>FETCH-LOGICAL-c448t-7c720cec22502d897abc765ffa79030ac10feae9937bab9de5d3d57bb25a1e613</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0939641118314887$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30836180$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jesus, Ana R.</creatorcontrib><creatorcontrib>Soromenho, Mário R.C.</creatorcontrib><creatorcontrib>Raposo, Luís R.</creatorcontrib><creatorcontrib>Esperança, José M.S.S.</creatorcontrib><creatorcontrib>Baptista, Pedro V.</creatorcontrib><creatorcontrib>Fernandes, Alexandra R.</creatorcontrib><creatorcontrib>Reis, Patrícia M.</creatorcontrib><title>Enhancement of water solubility of poorly water-soluble drugs by new biocompatible N-acetyl amino acid N-alkyl cholinium-based ionic liquids</title><title>European journal of pharmaceutics and biopharmaceutics</title><addtitle>Eur J Pharm Biopharm</addtitle><description>[Display omitted]
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 the 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 the water solubility of these drugs up to four times that in pure water or in an inorganic salt solution. In the presence of these ILs, the drugs lipophilicity (log P 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.</description><subject>Amino acids</subject><subject>Bioavailability</subject><subject>Cytotoxicity</subject><subject>Drug Delivery</subject><subject>Ionic Liquids</subject><issn>0939-6411</issn><issn>1873-3441</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kc1u1TAQhS0EopeWF2CBvGSTYMdJ7EhsUFV-pKps6Nryz4TOxYlTO6HKO_DQJNzCsquRzvnmSDOHkDeclZzx9v2xhONky4rxrmSiZKx-Rg5cSVGIuubPyYF1oivamvMz8irnI9sI2aiX5EwwJVqu2IH8vhrvzOhggHGmsacPZoZEcwyLxYDzumtTjCmsJ6v4awWgPi0_MrUrHeGBWowuDpOZcbduCuNgXgM1A46RGod-18LPTXJ3MeCIy1BYk8FTjCM6GvB-QZ8vyIvehAyvH-c5uf109f3yS3H97fPXy4_XhatrNRfSyYo5cFXVsMqrThrrZNv0vZEdE8w4znow0HVCWmM7D40XvpHWVo3h0HJxTt6dcqcU7xfIsx4wOwjBjBCXrCuuVNNxVasNrU6oSzHnBL2eEg4mrZozvbegj3pvQe8taCb09uNt6e1j_mIH8P9X_r19Az6cANiu_IWQdHYIWw0eE7hZ-4hP5f8Bp2ycAg</recordid><startdate>20190401</startdate><enddate>20190401</enddate><creator>Jesus, Ana R.</creator><creator>Soromenho, Mário R.C.</creator><creator>Raposo, Luís R.</creator><creator>Esperança, José M.S.S.</creator><creator>Baptista, Pedro V.</creator><creator>Fernandes, Alexandra R.</creator><creator>Reis, Patrícia M.</creator><general>Elsevier B.V</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20190401</creationdate><title>Enhancement of water solubility of poorly water-soluble drugs by new biocompatible N-acetyl amino acid N-alkyl cholinium-based ionic liquids</title><author>Jesus, Ana R. ; Soromenho, Mário R.C. ; Raposo, Luís R. ; Esperança, José M.S.S. ; Baptista, Pedro V. ; Fernandes, Alexandra R. ; Reis, Patrícia M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c448t-7c720cec22502d897abc765ffa79030ac10feae9937bab9de5d3d57bb25a1e613</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Amino acids</topic><topic>Bioavailability</topic><topic>Cytotoxicity</topic><topic>Drug Delivery</topic><topic>Ionic Liquids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jesus, Ana R.</creatorcontrib><creatorcontrib>Soromenho, Mário R.C.</creatorcontrib><creatorcontrib>Raposo, Luís R.</creatorcontrib><creatorcontrib>Esperança, José M.S.S.</creatorcontrib><creatorcontrib>Baptista, Pedro V.</creatorcontrib><creatorcontrib>Fernandes, Alexandra R.</creatorcontrib><creatorcontrib>Reis, Patrícia M.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>European journal of pharmaceutics and biopharmaceutics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jesus, Ana R.</au><au>Soromenho, Mário R.C.</au><au>Raposo, Luís R.</au><au>Esperança, José M.S.S.</au><au>Baptista, Pedro V.</au><au>Fernandes, Alexandra R.</au><au>Reis, Patrícia M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enhancement of water solubility of poorly water-soluble drugs by new biocompatible N-acetyl amino acid N-alkyl cholinium-based ionic liquids</atitle><jtitle>European journal of pharmaceutics and biopharmaceutics</jtitle><addtitle>Eur J Pharm Biopharm</addtitle><date>2019-04-01</date><risdate>2019</risdate><volume>137</volume><spage>227</spage><epage>232</epage><pages>227-232</pages><issn>0939-6411</issn><eissn>1873-3441</eissn><abstract>[Display omitted]
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 the 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 the water solubility of these drugs up to four times that in pure water or in an inorganic salt solution. In the presence of these ILs, the drugs lipophilicity (log P 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.</abstract><cop>Netherlands</cop><pub>Elsevier B.V</pub><pmid>30836180</pmid><doi>10.1016/j.ejpb.2019.03.004</doi><tpages>6</tpages></addata></record> |
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| source | Elsevier ScienceDirect Journals |
| subjects | Amino acids Bioavailability Cytotoxicity Drug Delivery Ionic Liquids |
| title | 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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