Novel Surfactants with Diglutamic Acid Polar Head Group: Drug Solubilization and Toxicity Studies
ABSTRACT Purpose Novel surfactants made of diglutamic acid (DG) polar head linked to lithocholic, arachidonic, linoleic or stearic acids were designed for drug solubilization. Methods Surfactants 3-D conformer and packing parameter were determined by molecular modelling and self-assembling propertie...
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| Veröffentlicht in: | Pharmaceutical research 2012-07, Vol.29 (7), p.1882-1896 |
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| creator | Ménard, Nathalie Tsapis, Nicolas Poirier, Cécile Arnauld, Thomas Moine, Laurence Gignoux, Claire Lefoulon, François Péan, Jean-Manuel Fattal, Elias |
| description | ABSTRACT
Purpose
Novel surfactants made of diglutamic acid (DG) polar head linked to lithocholic, arachidonic, linoleic or stearic acids were designed for drug solubilization.
Methods
Surfactants 3-D conformer and packing parameter were determined by molecular modelling and self-assembling properties by pyrene fluorescence measurements. Cytotoxicity was assessed on Human Umbilical Vein Endothelial Cells (HUVEC) and haemolyitic activity on rat red blood cells. Drug solubilization was quantified and its interaction with hydrophobic moieties was characterized using differential scanning calorimetry and X-ray diffraction. Self organisation of stearoyl-DG was observed by cryogenic transmission electron microscopy. Toxicity after repeated injections of stearoyl-DG was investigated in Wistar rats.
Results
DG-based surfactants self-assemble into water and their critical micellar concentrations are comprised between 200 and 920 μg/mL. Cytotoxicity and haemolysis were lower than for polysorbate 80. At best, stearoyl-DG solubilized the drug up to 22% (w/w). Solid-state characterization evidenced drug/lipid interactions leading to the formation of a new complex. Stearoyl-DG formed spherical micelles of 20 nm, as predicted by packing parameter calculation. However, it induced a possible liver toxicity after intravenous administration in rats.
Conclusions
Among the surfactants tested, stearoyl-DG is the more efficient for drug solubilization but its use is limited by its possible liver toxicity. |
| doi_str_mv | 10.1007/s11095-012-0714-8 |
| format | Article |
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Purpose
Novel surfactants made of diglutamic acid (DG) polar head linked to lithocholic, arachidonic, linoleic or stearic acids were designed for drug solubilization.
Methods
Surfactants 3-D conformer and packing parameter were determined by molecular modelling and self-assembling properties by pyrene fluorescence measurements. Cytotoxicity was assessed on Human Umbilical Vein Endothelial Cells (HUVEC) and haemolyitic activity on rat red blood cells. Drug solubilization was quantified and its interaction with hydrophobic moieties was characterized using differential scanning calorimetry and X-ray diffraction. Self organisation of stearoyl-DG was observed by cryogenic transmission electron microscopy. Toxicity after repeated injections of stearoyl-DG was investigated in Wistar rats.
Results
DG-based surfactants self-assemble into water and their critical micellar concentrations are comprised between 200 and 920 μg/mL. Cytotoxicity and haemolysis were lower than for polysorbate 80. At best, stearoyl-DG solubilized the drug up to 22% (w/w). Solid-state characterization evidenced drug/lipid interactions leading to the formation of a new complex. Stearoyl-DG formed spherical micelles of 20 nm, as predicted by packing parameter calculation. However, it induced a possible liver toxicity after intravenous administration in rats.
Conclusions
Among the surfactants tested, stearoyl-DG is the more efficient for drug solubilization but its use is limited by its possible liver toxicity.</description><identifier>ISSN: 0724-8741</identifier><identifier>EISSN: 1573-904X</identifier><identifier>DOI: 10.1007/s11095-012-0714-8</identifier><identifier>PMID: 22451248</identifier><identifier>CODEN: PHREEB</identifier><language>eng</language><publisher>Boston: Springer US</publisher><subject>Acids ; Animals ; Antineoplastic Agents - chemistry ; Arachidonic Acid - chemistry ; Arachidonic Acid - toxicity ; Biochemistry ; Biological and medical sciences ; Biomedical and Life Sciences ; Biomedical Engineering and Bioengineering ; Biomedicine ; Erythrocytes - drug effects ; General pharmacology ; Glutamic Acid - analogs & derivatives ; Glutamic Acid - toxicity ; Hemolysis - drug effects ; Human Umbilical Vein Endothelial Cells ; Humans ; Hydrophobic and Hydrophilic Interactions ; Life Sciences ; Linoleic Acid - chemistry ; Linoleic Acid - toxicity ; Lithocholic Acid - chemistry ; Lithocholic Acid - toxicity ; Medical Law ; Medical sciences ; Micelles ; Models, Molecular ; Pharmaceutical technology. Pharmaceutical industry ; Pharmacology. Drug treatments ; Pharmacology/Toxicology ; Pharmacy ; Rats ; Rats, Wistar ; Research Paper ; Solubility ; Stearic Acids - chemistry ; Stearic Acids - toxicity ; Surface-Active Agents - chemistry ; Surface-Active Agents - toxicity ; Surfactants ; Toxicity</subject><ispartof>Pharmaceutical research, 2012-07, Vol.29 (7), p.1882-1896</ispartof><rights>Springer Science+Business Media, LLC 2012</rights><rights>2015 INIST-CNRS</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c469t-84e215b2f39d8aa3d125957404cbd0a8ac2ec03cc47a5e3b4a9c6d6050ffd55f3</citedby><cites>FETCH-LOGICAL-c469t-84e215b2f39d8aa3d125957404cbd0a8ac2ec03cc47a5e3b4a9c6d6050ffd55f3</cites><orcidid>0000-0002-3194-961X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11095-012-0714-8$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11095-012-0714-8$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>230,314,780,784,885,27922,27923,41486,42555,51317</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26117506$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22451248$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-04101338$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Ménard, Nathalie</creatorcontrib><creatorcontrib>Tsapis, Nicolas</creatorcontrib><creatorcontrib>Poirier, Cécile</creatorcontrib><creatorcontrib>Arnauld, Thomas</creatorcontrib><creatorcontrib>Moine, Laurence</creatorcontrib><creatorcontrib>Gignoux, Claire</creatorcontrib><creatorcontrib>Lefoulon, François</creatorcontrib><creatorcontrib>Péan, Jean-Manuel</creatorcontrib><creatorcontrib>Fattal, Elias</creatorcontrib><title>Novel Surfactants with Diglutamic Acid Polar Head Group: Drug Solubilization and Toxicity Studies</title><title>Pharmaceutical research</title><addtitle>Pharm Res</addtitle><addtitle>Pharm Res</addtitle><description>ABSTRACT
Purpose
Novel surfactants made of diglutamic acid (DG) polar head linked to lithocholic, arachidonic, linoleic or stearic acids were designed for drug solubilization.
Methods
Surfactants 3-D conformer and packing parameter were determined by molecular modelling and self-assembling properties by pyrene fluorescence measurements. Cytotoxicity was assessed on Human Umbilical Vein Endothelial Cells (HUVEC) and haemolyitic activity on rat red blood cells. Drug solubilization was quantified and its interaction with hydrophobic moieties was characterized using differential scanning calorimetry and X-ray diffraction. Self organisation of stearoyl-DG was observed by cryogenic transmission electron microscopy. Toxicity after repeated injections of stearoyl-DG was investigated in Wistar rats.
Results
DG-based surfactants self-assemble into water and their critical micellar concentrations are comprised between 200 and 920 μg/mL. Cytotoxicity and haemolysis were lower than for polysorbate 80. At best, stearoyl-DG solubilized the drug up to 22% (w/w). Solid-state characterization evidenced drug/lipid interactions leading to the formation of a new complex. Stearoyl-DG formed spherical micelles of 20 nm, as predicted by packing parameter calculation. However, it induced a possible liver toxicity after intravenous administration in rats.
Conclusions
Among the surfactants tested, stearoyl-DG is the more efficient for drug solubilization but its use is limited by its possible liver toxicity.</description><subject>Acids</subject><subject>Animals</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Arachidonic Acid - chemistry</subject><subject>Arachidonic Acid - toxicity</subject><subject>Biochemistry</subject><subject>Biological and medical sciences</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedical Engineering and Bioengineering</subject><subject>Biomedicine</subject><subject>Erythrocytes - drug effects</subject><subject>General pharmacology</subject><subject>Glutamic Acid - analogs & derivatives</subject><subject>Glutamic Acid - toxicity</subject><subject>Hemolysis - drug effects</subject><subject>Human Umbilical Vein Endothelial Cells</subject><subject>Humans</subject><subject>Hydrophobic and Hydrophilic Interactions</subject><subject>Life Sciences</subject><subject>Linoleic Acid - chemistry</subject><subject>Linoleic Acid - toxicity</subject><subject>Lithocholic Acid - chemistry</subject><subject>Lithocholic Acid - toxicity</subject><subject>Medical Law</subject><subject>Medical sciences</subject><subject>Micelles</subject><subject>Models, Molecular</subject><subject>Pharmaceutical technology. Pharmaceutical industry</subject><subject>Pharmacology. Drug treatments</subject><subject>Pharmacology/Toxicology</subject><subject>Pharmacy</subject><subject>Rats</subject><subject>Rats, Wistar</subject><subject>Research Paper</subject><subject>Solubility</subject><subject>Stearic Acids - chemistry</subject><subject>Stearic Acids - toxicity</subject><subject>Surface-Active Agents - chemistry</subject><subject>Surface-Active Agents - toxicity</subject><subject>Surfactants</subject><subject>Toxicity</subject><issn>0724-8741</issn><issn>1573-904X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><recordid>eNp10VGL1DAQB_AiireefgBfJCCCPlQzadKmvi13eissKuwJvoVpku7lyDZr0pyen94uXU8RfApMfjOZ8C-Kp0BfA6XNmwRAW1FSYCVtgJfyXrEA0VRlS_nX-8WCNmwqNhxOikcpXVNKJbT8YXHCGBfAuFwU-DHcWE82OfaoRxzGRL678Yqcu63PI-6cJkvtDPkcPEaysmjIRQx5_5acx7wlm-Bz57z7iaMLA8HBkMvww2k33pLNmI2z6XHxoEef7JPjeVp8ef_u8mxVrj9dfDhbrkvN63YsJbcMRMf6qjUSsTLARCsaTrnuDEWJmllNK615g8JWHcdW16amgva9EaKvTotX89wr9Gof3Q7jrQro1Gq5Voca5UChquQNTPblbPcxfMs2jWrnkrbe42BDTgo4tJVoa8Yn-vwfeh1yHKafqGmclII3ICcFs9IxpBRtf7cBUHXISs1ZqSkrdchKHXqeHSfnbmfNXcfvcCbw4ggwafR9xEG79MfVAI2g9eTY7NJ0NWxt_HvF_73-C8Sjqlc</recordid><startdate>20120701</startdate><enddate>20120701</enddate><creator>Ménard, Nathalie</creator><creator>Tsapis, Nicolas</creator><creator>Poirier, Cécile</creator><creator>Arnauld, Thomas</creator><creator>Moine, Laurence</creator><creator>Gignoux, Claire</creator><creator>Lefoulon, François</creator><creator>Péan, Jean-Manuel</creator><creator>Fattal, Elias</creator><general>Springer US</general><general>Springer</general><general>Springer Nature B.V</general><general>American Association of Pharmaceutical Scientists</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7RV</scope><scope>7TK</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8AO</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>KB0</scope><scope>M0S</scope><scope>M1P</scope><scope>NAPCQ</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7QO</scope><scope>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0002-3194-961X</orcidid></search><sort><creationdate>20120701</creationdate><title>Novel Surfactants with Diglutamic Acid Polar Head Group: Drug Solubilization and Toxicity Studies</title><author>Ménard, Nathalie ; Tsapis, Nicolas ; Poirier, Cécile ; Arnauld, Thomas ; Moine, Laurence ; Gignoux, Claire ; Lefoulon, François ; Péan, Jean-Manuel ; Fattal, Elias</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c469t-84e215b2f39d8aa3d125957404cbd0a8ac2ec03cc47a5e3b4a9c6d6050ffd55f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Acids</topic><topic>Animals</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Arachidonic Acid - chemistry</topic><topic>Arachidonic Acid - toxicity</topic><topic>Biochemistry</topic><topic>Biological and medical sciences</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedical Engineering and Bioengineering</topic><topic>Biomedicine</topic><topic>Erythrocytes - drug effects</topic><topic>General pharmacology</topic><topic>Glutamic Acid - analogs & derivatives</topic><topic>Glutamic Acid - toxicity</topic><topic>Hemolysis - drug effects</topic><topic>Human Umbilical Vein Endothelial Cells</topic><topic>Humans</topic><topic>Hydrophobic and Hydrophilic Interactions</topic><topic>Life Sciences</topic><topic>Linoleic Acid - chemistry</topic><topic>Linoleic Acid - toxicity</topic><topic>Lithocholic Acid - chemistry</topic><topic>Lithocholic Acid - toxicity</topic><topic>Medical Law</topic><topic>Medical sciences</topic><topic>Micelles</topic><topic>Models, Molecular</topic><topic>Pharmaceutical technology. Pharmaceutical industry</topic><topic>Pharmacology. Drug treatments</topic><topic>Pharmacology/Toxicology</topic><topic>Pharmacy</topic><topic>Rats</topic><topic>Rats, Wistar</topic><topic>Research Paper</topic><topic>Solubility</topic><topic>Stearic Acids - chemistry</topic><topic>Stearic Acids - toxicity</topic><topic>Surface-Active Agents - chemistry</topic><topic>Surface-Active Agents - toxicity</topic><topic>Surfactants</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ménard, Nathalie</creatorcontrib><creatorcontrib>Tsapis, Nicolas</creatorcontrib><creatorcontrib>Poirier, Cécile</creatorcontrib><creatorcontrib>Arnauld, Thomas</creatorcontrib><creatorcontrib>Moine, Laurence</creatorcontrib><creatorcontrib>Gignoux, Claire</creatorcontrib><creatorcontrib>Lefoulon, François</creatorcontrib><creatorcontrib>Péan, Jean-Manuel</creatorcontrib><creatorcontrib>Fattal, Elias</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Nursing & Allied Health Database</collection><collection>Neurosciences Abstracts</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Nursing & Allied Health Database (Alumni Edition)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Nursing & Allied Health Premium</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>Biotechnology Research Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>Pharmaceutical research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ménard, Nathalie</au><au>Tsapis, Nicolas</au><au>Poirier, Cécile</au><au>Arnauld, Thomas</au><au>Moine, Laurence</au><au>Gignoux, Claire</au><au>Lefoulon, François</au><au>Péan, Jean-Manuel</au><au>Fattal, Elias</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel Surfactants with Diglutamic Acid Polar Head Group: Drug Solubilization and Toxicity Studies</atitle><jtitle>Pharmaceutical research</jtitle><stitle>Pharm Res</stitle><addtitle>Pharm Res</addtitle><date>2012-07-01</date><risdate>2012</risdate><volume>29</volume><issue>7</issue><spage>1882</spage><epage>1896</epage><pages>1882-1896</pages><issn>0724-8741</issn><eissn>1573-904X</eissn><coden>PHREEB</coden><abstract>ABSTRACT
Purpose
Novel surfactants made of diglutamic acid (DG) polar head linked to lithocholic, arachidonic, linoleic or stearic acids were designed for drug solubilization.
Methods
Surfactants 3-D conformer and packing parameter were determined by molecular modelling and self-assembling properties by pyrene fluorescence measurements. Cytotoxicity was assessed on Human Umbilical Vein Endothelial Cells (HUVEC) and haemolyitic activity on rat red blood cells. Drug solubilization was quantified and its interaction with hydrophobic moieties was characterized using differential scanning calorimetry and X-ray diffraction. Self organisation of stearoyl-DG was observed by cryogenic transmission electron microscopy. Toxicity after repeated injections of stearoyl-DG was investigated in Wistar rats.
Results
DG-based surfactants self-assemble into water and their critical micellar concentrations are comprised between 200 and 920 μg/mL. Cytotoxicity and haemolysis were lower than for polysorbate 80. At best, stearoyl-DG solubilized the drug up to 22% (w/w). Solid-state characterization evidenced drug/lipid interactions leading to the formation of a new complex. Stearoyl-DG formed spherical micelles of 20 nm, as predicted by packing parameter calculation. However, it induced a possible liver toxicity after intravenous administration in rats.
Conclusions
Among the surfactants tested, stearoyl-DG is the more efficient for drug solubilization but its use is limited by its possible liver toxicity.</abstract><cop>Boston</cop><pub>Springer US</pub><pmid>22451248</pmid><doi>10.1007/s11095-012-0714-8</doi><tpages>15</tpages><orcidid>https://orcid.org/0000-0002-3194-961X</orcidid><oa>free_for_read</oa></addata></record> |
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| ispartof | Pharmaceutical research, 2012-07, Vol.29 (7), p.1882-1896 |
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| language | eng |
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| source | MEDLINE; SpringerLink Journals - AutoHoldings |
| subjects | Acids Animals Antineoplastic Agents - chemistry Arachidonic Acid - chemistry Arachidonic Acid - toxicity Biochemistry Biological and medical sciences Biomedical and Life Sciences Biomedical Engineering and Bioengineering Biomedicine Erythrocytes - drug effects General pharmacology Glutamic Acid - analogs & derivatives Glutamic Acid - toxicity Hemolysis - drug effects Human Umbilical Vein Endothelial Cells Humans Hydrophobic and Hydrophilic Interactions Life Sciences Linoleic Acid - chemistry Linoleic Acid - toxicity Lithocholic Acid - chemistry Lithocholic Acid - toxicity Medical Law Medical sciences Micelles Models, Molecular Pharmaceutical technology. Pharmaceutical industry Pharmacology. Drug treatments Pharmacology/Toxicology Pharmacy Rats Rats, Wistar Research Paper Solubility Stearic Acids - chemistry Stearic Acids - toxicity Surface-Active Agents - chemistry Surface-Active Agents - toxicity Surfactants Toxicity |
| title | Novel Surfactants with Diglutamic Acid Polar Head Group: Drug Solubilization and Toxicity Studies |
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