pH-responsive polymeric micelles of poly(ethylene glycol)- b-poly(alkyl(meth)acrylate- co-methacrylic acid): Influence of the copolymer composition on self-assembling properties and release of candesartan cilexetil
The objective of the present study was to investigate the influence of chemical structure and molecular weight of pH-sensitive block copolymers on their self-assembling properties, the loading and the release of candesartan cilexetil (CDN). Block copolymers of poly(ethylene glycol) and t-butyl metha...
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| Veröffentlicht in: | European journal of pharmaceutics and biopharmaceutics 2007-03, Vol.65 (3), p.379-387 |
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| container_title | European journal of pharmaceutics and biopharmaceutics |
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| creator | Satturwar, Prashant Eddine, Mohamad Nasser Ravenelle, François Leroux, Jean-Christophe |
| description | The objective of the present study was to investigate the influence of chemical structure and molecular weight of pH-sensitive block copolymers on their self-assembling properties, the loading and the release of candesartan cilexetil (CDN). Block copolymers of poly(ethylene glycol) and
t-butyl methacrylate,
iso-butyl acrylate,
n-butyl acrylate or propyl methacrylate were synthesized by atom transfer radical polymerization. pH-sensitivity was obtained by hydrolysis of
t-butyl groups. The poorly water-soluble drug CDN was incorporated in the micelles and the
in vitro drug release was evaluated as a function of pH. The critical aggregation concentration of hydrolyzed copolymers (p
K
a
=
6.2–6.6) was higher compared to the unhydrolyzed ones. Dynamic light scattering studies and atomic force microscopy images revealed uniform size micelles with aggregation numbers ranging from 60 to 160. The entrapment efficiency of CDN was generally found to be above 90%, with drug loading levels reaching ∼20% (w/w). Differential scanning calorimetry studies showed the amorphous nature of entrapped CDN. The release of CDN from pH-sensitive micelles was triggered upon an increase in pH from 1.2 to 7.2. These findings suggest that the PEG-
b-poly(alkyl(meth)acrylate-
co-methacrylic acid)s can self-assemble to form micelles which exhibit high loading capacities for CDN and release the drug in a pH-dependent fashion. |
| doi_str_mv | 10.1016/j.ejpb.2006.09.012 |
| format | Article |
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t-butyl methacrylate,
iso-butyl acrylate,
n-butyl acrylate or propyl methacrylate were synthesized by atom transfer radical polymerization. pH-sensitivity was obtained by hydrolysis of
t-butyl groups. The poorly water-soluble drug CDN was incorporated in the micelles and the
in vitro drug release was evaluated as a function of pH. The critical aggregation concentration of hydrolyzed copolymers (p
K
a
=
6.2–6.6) was higher compared to the unhydrolyzed ones. Dynamic light scattering studies and atomic force microscopy images revealed uniform size micelles with aggregation numbers ranging from 60 to 160. The entrapment efficiency of CDN was generally found to be above 90%, with drug loading levels reaching ∼20% (w/w). Differential scanning calorimetry studies showed the amorphous nature of entrapped CDN. The release of CDN from pH-sensitive micelles was triggered upon an increase in pH from 1.2 to 7.2. These findings suggest that the PEG-
b-poly(alkyl(meth)acrylate-
co-methacrylic acid)s can self-assemble to form micelles which exhibit high loading capacities for CDN and release the drug in a pH-dependent fashion.</description><identifier>ISSN: 0939-6411</identifier><identifier>EISSN: 1873-3441</identifier><identifier>DOI: 10.1016/j.ejpb.2006.09.012</identifier><identifier>PMID: 17123802</identifier><language>eng</language><publisher>Netherlands: Elsevier B.V</publisher><subject>Angiotensin II Type 1 Receptor Blockers - chemistry ; Atom transfer radical polymerization ; Benzimidazoles - chemistry ; Biphenyl Compounds - chemistry ; Calorimetry, Differential Scanning ; Candesartan cilexetil ; Chemistry, Pharmaceutical ; Critical aggregation concentration ; Drug Carriers ; Drug Compounding ; Drug solubilization ; Gastric Juice - chemistry ; Hydrogen-Ion Concentration ; Hydrolysis ; Light ; Methacrylates - chemical synthesis ; Methacrylates - chemistry ; Micelles ; Microscopy, Atomic Force ; Molecular Structure ; Molecular Weight ; Oral delivery ; Particle Size ; pH-sensitivity ; Poly(ethylene glycol)- b-poly(alkyl(meth)acrylate- co-methacrylic acid) ; Polyethylene Glycols - chemical synthesis ; Polyethylene Glycols - chemistry ; Polymeric micelles ; Polymethacrylic Acids - chemical synthesis ; Polymethacrylic Acids - chemistry ; Scattering, Radiation ; Solubility ; Solvent evaporation ; Technology, Pharmaceutical - methods ; Temperature ; Tetrazoles - chemistry ; Time Factors ; Water - chemistry</subject><ispartof>European journal of pharmaceutics and biopharmaceutics, 2007-03, Vol.65 (3), p.379-387</ispartof><rights>2006 Elsevier B.V.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c420t-37f89bedd415b07d711acf78b49004fbae30d4b74463ef31a9185d8cc73749c03</citedby><cites>FETCH-LOGICAL-c420t-37f89bedd415b07d711acf78b49004fbae30d4b74463ef31a9185d8cc73749c03</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ejpb.2006.09.012$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27922,27923,45993</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17123802$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Satturwar, Prashant</creatorcontrib><creatorcontrib>Eddine, Mohamad Nasser</creatorcontrib><creatorcontrib>Ravenelle, François</creatorcontrib><creatorcontrib>Leroux, Jean-Christophe</creatorcontrib><title>pH-responsive polymeric micelles of poly(ethylene glycol)- b-poly(alkyl(meth)acrylate- co-methacrylic acid): Influence of the copolymer composition on self-assembling properties and release of candesartan cilexetil</title><title>European journal of pharmaceutics and biopharmaceutics</title><addtitle>Eur J Pharm Biopharm</addtitle><description>The objective of the present study was to investigate the influence of chemical structure and molecular weight of pH-sensitive block copolymers on their self-assembling properties, the loading and the release of candesartan cilexetil (CDN). Block copolymers of poly(ethylene glycol) and
t-butyl methacrylate,
iso-butyl acrylate,
n-butyl acrylate or propyl methacrylate were synthesized by atom transfer radical polymerization. pH-sensitivity was obtained by hydrolysis of
t-butyl groups. The poorly water-soluble drug CDN was incorporated in the micelles and the
in vitro drug release was evaluated as a function of pH. The critical aggregation concentration of hydrolyzed copolymers (p
K
a
=
6.2–6.6) was higher compared to the unhydrolyzed ones. Dynamic light scattering studies and atomic force microscopy images revealed uniform size micelles with aggregation numbers ranging from 60 to 160. The entrapment efficiency of CDN was generally found to be above 90%, with drug loading levels reaching ∼20% (w/w). Differential scanning calorimetry studies showed the amorphous nature of entrapped CDN. The release of CDN from pH-sensitive micelles was triggered upon an increase in pH from 1.2 to 7.2. These findings suggest that the PEG-
b-poly(alkyl(meth)acrylate-
co-methacrylic acid)s can self-assemble to form micelles which exhibit high loading capacities for CDN and release the drug in a pH-dependent fashion.</description><subject>Angiotensin II Type 1 Receptor Blockers - chemistry</subject><subject>Atom transfer radical polymerization</subject><subject>Benzimidazoles - chemistry</subject><subject>Biphenyl Compounds - chemistry</subject><subject>Calorimetry, Differential Scanning</subject><subject>Candesartan cilexetil</subject><subject>Chemistry, Pharmaceutical</subject><subject>Critical aggregation concentration</subject><subject>Drug Carriers</subject><subject>Drug Compounding</subject><subject>Drug solubilization</subject><subject>Gastric Juice - chemistry</subject><subject>Hydrogen-Ion Concentration</subject><subject>Hydrolysis</subject><subject>Light</subject><subject>Methacrylates - chemical synthesis</subject><subject>Methacrylates - chemistry</subject><subject>Micelles</subject><subject>Microscopy, Atomic Force</subject><subject>Molecular Structure</subject><subject>Molecular Weight</subject><subject>Oral delivery</subject><subject>Particle Size</subject><subject>pH-sensitivity</subject><subject>Poly(ethylene glycol)- b-poly(alkyl(meth)acrylate- co-methacrylic acid)</subject><subject>Polyethylene Glycols - chemical synthesis</subject><subject>Polyethylene Glycols - chemistry</subject><subject>Polymeric micelles</subject><subject>Polymethacrylic Acids - chemical synthesis</subject><subject>Polymethacrylic Acids - chemistry</subject><subject>Scattering, Radiation</subject><subject>Solubility</subject><subject>Solvent evaporation</subject><subject>Technology, Pharmaceutical - methods</subject><subject>Temperature</subject><subject>Tetrazoles - chemistry</subject><subject>Time Factors</subject><subject>Water - chemistry</subject><issn>0939-6411</issn><issn>1873-3441</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9UcGOFCEUJEbjjqs_4MFwMjsHWmiYptvsxWzU3WQTL3omNLzeZaSbFpiN_aN-j_TMJN5MSIB69YpHFUJvGa0YZc2HfQX7ua9qSpuKdhVl9TO0Ya3khAvBnqMN7XhHGsHYBXqV0p5SKuSufYkumGQ1b2m9QX_mWxIhzWFK7gnwHPwyQnQGj86A95BwGI7oFeTHxcME-MEvJvgtwT05FrT_ufirsdS32sTF6wwEm0BW5AgUNW2c3X7Ed9PgDzAZWFXzIxTa-cVyGueQXHZhwmUl8APRKcHYezc94DmGGWJ2ZSA9WRzBg05HGVPukHTMesLGefgN2fnX6MWgfYI35_0S_fjy-fvNLbn_9vXu5tM9MaKmmXA5tF0P1gq266m0kjFtBtn2oiteDb0GTq3opRANh4Ez3bF2Z1tjJJeiM5Rfovcn3TLfrwOkrEaXVuP0BOGQlKR13XAqCrE-EU0MKUUY1BzdqOOiGFVrmmqv1jTVmqainSpplqZ3Z_VDP4L913KOrxCuTwQof3xyEFUybvXXuggmKxvc__T_AqZ4tsQ</recordid><startdate>20070301</startdate><enddate>20070301</enddate><creator>Satturwar, Prashant</creator><creator>Eddine, Mohamad Nasser</creator><creator>Ravenelle, François</creator><creator>Leroux, Jean-Christophe</creator><general>Elsevier B.V</general><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>7X8</scope></search><sort><creationdate>20070301</creationdate><title>pH-responsive polymeric micelles of poly(ethylene glycol)- b-poly(alkyl(meth)acrylate- co-methacrylic acid): Influence of the copolymer composition on self-assembling properties and release of candesartan cilexetil</title><author>Satturwar, Prashant ; Eddine, Mohamad Nasser ; Ravenelle, François ; Leroux, Jean-Christophe</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c420t-37f89bedd415b07d711acf78b49004fbae30d4b74463ef31a9185d8cc73749c03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Angiotensin II Type 1 Receptor Blockers - chemistry</topic><topic>Atom transfer radical polymerization</topic><topic>Benzimidazoles - chemistry</topic><topic>Biphenyl Compounds - chemistry</topic><topic>Calorimetry, Differential Scanning</topic><topic>Candesartan cilexetil</topic><topic>Chemistry, Pharmaceutical</topic><topic>Critical aggregation concentration</topic><topic>Drug Carriers</topic><topic>Drug Compounding</topic><topic>Drug solubilization</topic><topic>Gastric Juice - chemistry</topic><topic>Hydrogen-Ion Concentration</topic><topic>Hydrolysis</topic><topic>Light</topic><topic>Methacrylates - chemical synthesis</topic><topic>Methacrylates - chemistry</topic><topic>Micelles</topic><topic>Microscopy, Atomic Force</topic><topic>Molecular Structure</topic><topic>Molecular Weight</topic><topic>Oral delivery</topic><topic>Particle Size</topic><topic>pH-sensitivity</topic><topic>Poly(ethylene glycol)- b-poly(alkyl(meth)acrylate- co-methacrylic acid)</topic><topic>Polyethylene Glycols - chemical synthesis</topic><topic>Polyethylene Glycols - chemistry</topic><topic>Polymeric micelles</topic><topic>Polymethacrylic Acids - chemical synthesis</topic><topic>Polymethacrylic Acids - chemistry</topic><topic>Scattering, Radiation</topic><topic>Solubility</topic><topic>Solvent evaporation</topic><topic>Technology, Pharmaceutical - methods</topic><topic>Temperature</topic><topic>Tetrazoles - chemistry</topic><topic>Time Factors</topic><topic>Water - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Satturwar, Prashant</creatorcontrib><creatorcontrib>Eddine, Mohamad Nasser</creatorcontrib><creatorcontrib>Ravenelle, François</creatorcontrib><creatorcontrib>Leroux, Jean-Christophe</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><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>Satturwar, Prashant</au><au>Eddine, Mohamad Nasser</au><au>Ravenelle, François</au><au>Leroux, Jean-Christophe</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>pH-responsive polymeric micelles of poly(ethylene glycol)- b-poly(alkyl(meth)acrylate- co-methacrylic acid): Influence of the copolymer composition on self-assembling properties and release of candesartan cilexetil</atitle><jtitle>European journal of pharmaceutics and biopharmaceutics</jtitle><addtitle>Eur J Pharm Biopharm</addtitle><date>2007-03-01</date><risdate>2007</risdate><volume>65</volume><issue>3</issue><spage>379</spage><epage>387</epage><pages>379-387</pages><issn>0939-6411</issn><eissn>1873-3441</eissn><abstract>The objective of the present study was to investigate the influence of chemical structure and molecular weight of pH-sensitive block copolymers on their self-assembling properties, the loading and the release of candesartan cilexetil (CDN). Block copolymers of poly(ethylene glycol) and
t-butyl methacrylate,
iso-butyl acrylate,
n-butyl acrylate or propyl methacrylate were synthesized by atom transfer radical polymerization. pH-sensitivity was obtained by hydrolysis of
t-butyl groups. The poorly water-soluble drug CDN was incorporated in the micelles and the
in vitro drug release was evaluated as a function of pH. The critical aggregation concentration of hydrolyzed copolymers (p
K
a
=
6.2–6.6) was higher compared to the unhydrolyzed ones. Dynamic light scattering studies and atomic force microscopy images revealed uniform size micelles with aggregation numbers ranging from 60 to 160. The entrapment efficiency of CDN was generally found to be above 90%, with drug loading levels reaching ∼20% (w/w). Differential scanning calorimetry studies showed the amorphous nature of entrapped CDN. The release of CDN from pH-sensitive micelles was triggered upon an increase in pH from 1.2 to 7.2. These findings suggest that the PEG-
b-poly(alkyl(meth)acrylate-
co-methacrylic acid)s can self-assemble to form micelles which exhibit high loading capacities for CDN and release the drug in a pH-dependent fashion.</abstract><cop>Netherlands</cop><pub>Elsevier B.V</pub><pmid>17123802</pmid><doi>10.1016/j.ejpb.2006.09.012</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0939-6411 |
| ispartof | European journal of pharmaceutics and biopharmaceutics, 2007-03, Vol.65 (3), p.379-387 |
| issn | 0939-6411 1873-3441 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Angiotensin II Type 1 Receptor Blockers - chemistry Atom transfer radical polymerization Benzimidazoles - chemistry Biphenyl Compounds - chemistry Calorimetry, Differential Scanning Candesartan cilexetil Chemistry, Pharmaceutical Critical aggregation concentration Drug Carriers Drug Compounding Drug solubilization Gastric Juice - chemistry Hydrogen-Ion Concentration Hydrolysis Light Methacrylates - chemical synthesis Methacrylates - chemistry Micelles Microscopy, Atomic Force Molecular Structure Molecular Weight Oral delivery Particle Size pH-sensitivity Poly(ethylene glycol)- b-poly(alkyl(meth)acrylate- co-methacrylic acid) Polyethylene Glycols - chemical synthesis Polyethylene Glycols - chemistry Polymeric micelles Polymethacrylic Acids - chemical synthesis Polymethacrylic Acids - chemistry Scattering, Radiation Solubility Solvent evaporation Technology, Pharmaceutical - methods Temperature Tetrazoles - chemistry Time Factors Water - chemistry |
| title | pH-responsive polymeric micelles of poly(ethylene glycol)- b-poly(alkyl(meth)acrylate- co-methacrylic acid): Influence of the copolymer composition on self-assembling properties and release of candesartan cilexetil |
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