Chemoenzymatic synthesis, characterization, and controlled release of functional polymeric prodrugs with acyclovir as pendant
Identifieur interne : 000F02 ( Istex/Corpus ); précédent : 000F01; suivant : 000F03Chemoenzymatic synthesis, characterization, and controlled release of functional polymeric prodrugs with acyclovir as pendant
Auteurs : Xia Li ; Qi Wu ; Fu Zhang ; Xian-Fu LinSource :
- Journal of Applied Polymer Science [ 0021-8995 ] ; 2008-04-05.
Abstract
An efficient protocol for the synthesis of functional polymeric prodrugs of acyclovir with variable copolymer composition and potential liver‐targeting delivery was achieved by combining enzymatic selective synthesis of polymerizable acyclovir derivatives with radical copolymerization of properly selected comonomers. Vinyl D‐galactose ester (VAG), acrylic acid (AA), and methyl methacrylate (MMA) were chosen as comonomers and three novel polymeric prodrugs with acyclovir as pendant were synthesized using 2,2′‐azo‐bis‐iso‐butyronitrile (AIBN) as initiator in N,N‐dimethylformamide (DMF). The resulting polymers were characterized by FTIR, NMR, and GPC. The influence of the concentration of initiator and the molar ratio of comonomers on the polymerization was investigated. In vitro drug release studies showed that acyclovir could be released from poly(2‐N‐vinylsebacyl‐acyclovir‐co‐methyl methacrylate) (poly(VSA‐co‐MMA)), and the total released acyclovir after 7 days in buffer solution at pH 1.2 and 7.4 was ∼ 35% and 29%, respectively. Also, homopolymers of vinyl acyclovir derivatives with high drug payload (>50 wt %) were obtained and characterized by the same methods. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2008
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DOI: 10.1002/app.27680
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Vinyl D‐galactose ester (VAG), acrylic acid (AA), and methyl methacrylate (MMA) were chosen as comonomers and three novel polymeric prodrugs with acyclovir as pendant were synthesized using 2,2′‐azo‐bis‐iso‐butyronitrile (AIBN) as initiator in N,N‐dimethylformamide (DMF). The resulting polymers were characterized by FTIR, NMR, and GPC. The influence of the concentration of initiator and the molar ratio of comonomers on the polymerization was investigated. In vitro drug release studies showed that acyclovir could be released from poly(2‐N‐vinylsebacyl‐acyclovir‐co‐methyl methacrylate) (poly(VSA‐co‐MMA)), and the total released acyclovir after 7 days in buffer solution at pH 1.2 and 7.4 was ∼ 35% and 29%, respectively. Also, homopolymers of vinyl acyclovir derivatives with high drug payload (>50 wt %) were obtained and characterized by the same methods. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2008</div></front></TEI><istex><corpusName>wiley</corpusName><keywords><teeft><json:string>acyclovir</json:string><json:string>prodrugs</json:string><json:string>polymeric prodrugs</json:string><json:string>comonomers</json:string><json:string>molar ratio</json:string><json:string>buffer solution</json:string><json:string>prodrug</json:string><json:string>hplc</json:string><json:string>polymer</json:string><json:string>polymeric</json:string><json:string>pharm</json:string><json:string>copolymer</json:string><json:string>polymeric prodrug</json:string><json:string>chem</json:string><json:string>polymer science</json:string><json:string>vinyl acyclovir amide</json:string><json:string>amide</json:string><json:string>functional polymeric prodrugs</json:string><json:string>molar</json:string><json:string>drug release study</json:string><json:string>same method</json:string><json:string>phosphate buffer solution</json:string><json:string>radical polymerization</json:string><json:string>acyclovir microcapsules</json:string><json:string>pendant</json:string><json:string>qualitative analysis</json:string><json:string>light yellow solid</json:string><json:string>radical copolymerization</json:string><json:string>mobile phase</json:string><json:string>molecular weight</json:string><json:string>vinyl acyclovir derivative</json:string></teeft></keywords><author><json:item><name>Xia Li</name><affiliations><json:string>Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China</json:string></affiliations></json:item><json:item><name>Qi Wu</name><affiliations><json:string>Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China</json:string></affiliations></json:item><json:item><name>Fu Zhang</name><affiliations><json:string>Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China</json:string></affiliations></json:item><json:item><name>Xian‐Fu Lin</name><affiliations><json:string>Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China</json:string><json:string>E-mail: llc123@zju.edu.cn</json:string><json:string>Correspondence address: Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China===</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>drug delivery systems</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>enzymes</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>copolymerization</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>acyclovir</value></json:item></subject><articleId><json:string>APP27680</json:string></articleId><arkIstex>ark:/67375/WNG-R0VDQRR4-N</arkIstex><language><json:string>eng</json:string></language><originalGenre><json:string>article</json:string></originalGenre><abstract>An efficient protocol for the synthesis of functional polymeric prodrugs of acyclovir with variable copolymer composition and potential liver‐targeting delivery was achieved by combining enzymatic selective synthesis of polymerizable acyclovir derivatives with radical copolymerization of properly selected comonomers. Vinyl D‐galactose ester (VAG), acrylic acid (AA), and methyl methacrylate (MMA) were chosen as comonomers and three novel polymeric prodrugs with acyclovir as pendant were synthesized using 2,2′‐azo‐bis‐iso‐butyronitrile (AIBN) as initiator in N,N‐dimethylformamide (DMF). The resulting polymers were characterized by FTIR, NMR, and GPC. The influence of the concentration of initiator and the molar ratio of comonomers on the polymerization was investigated. In vitro drug release studies showed that acyclovir could be released from poly(2‐N‐vinylsebacyl‐acyclovir‐co‐methyl methacrylate) (poly(VSA‐co‐MMA)), and the total released acyclovir after 7 days in buffer solution at pH 1.2 and 7.4 was ∼ 35% and 29%, respectively. Also, homopolymers of vinyl acyclovir derivatives with high drug payload (>50 wt %) were obtained and characterized by the same methods. © 2007 Wiley Periodicals, Inc. 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The influence of the concentration of initiator and the molar ratio of comonomers on the polymerization was investigated. <hi rend="italic">In vitro</hi> drug release studies showed that acyclovir could be released from poly(2‐<hi rend="italic">N</hi>‐vinylsebacyl‐acyclovir‐<hi rend="italic">co</hi>‐methyl methacrylate) (poly(VSA‐<hi rend="italic">co</hi>‐MMA)), and the total released acyclovir after 7 days in buffer solution at pH 1.2 and 7.4 was ∼ 35% and 29%, respectively. Also, homopolymers of vinyl acyclovir derivatives with high drug payload (>50 wt %) were obtained and characterized by the same methods. © 2007 Wiley Periodicals, Inc. 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Sci.</title></titleGroup></publicationMeta><publicationMeta level="part" position="10"><doi origin="wiley" registered="yes">10.1002/app.v108:1</doi><numberingGroup><numbering type="journalVolume" number="108">108</numbering><numbering type="journalIssue">1</numbering></numberingGroup><coverDate startDate="2008-04-05">5 April 2008</coverDate></publicationMeta><publicationMeta level="unit" type="article" position="285" status="forIssue"><doi origin="wiley" registered="yes">10.1002/app.27680</doi><idGroup><id type="unit" value="APP27680"></id></idGroup><countGroup><count type="pageTotal" number="7"></count></countGroup><copyright ownership="publisher">Copyright © 2007 Wiley Periodicals, Inc.</copyright><eventGroup><event type="manuscriptReceived" date="2007-03-10"></event><event type="manuscriptAccepted" date="2007-09-01"></event><event type="publishedOnlineEarlyUnpaginated" date="2007-12-28"></event><event type="firstOnline" date="2007-12-28"></event><event type="publishedOnlineFinalForm" date="2008-01-17"></event><event type="xmlConverted" agent="Converter:JWSART34_TO_WML3G version:2.3.2 mode:FullText source:FullText result:FullText" date="2010-03-05"></event><event type="xmlConverted" agent="Converter:WILEY_ML3G_TO_WILEY_ML3GV2 version:4.0.1" date="2014-03-24"></event><event type="xmlConverted" agent="Converter:WML3G_To_WML3G version:4.1.7 mode:FullText,remove_FC" date="2014-10-24"></event></eventGroup><numberingGroup><numbering type="pageFirst">431</numbering><numbering type="pageLast">437</numbering></numberingGroup><correspondenceTo>Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China===</correspondenceTo><objectNameGroup><objectName elementName="figure">Scheme</objectName></objectNameGroup><linkGroup><link type="toTypesetVersion" href="file:APP.APP27680.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="5"></count><count type="tableTotal" number="1"></count><count type="referenceTotal" number="33"></count><count type="wordTotal" number="3986"></count></countGroup><titleGroup><title type="main" xml:lang="en">Chemoenzymatic synthesis, characterization, and controlled release of functional polymeric prodrugs with acyclovir as pendant</title><title type="short" xml:lang="en">Polymeric Prodrugs with Acyclovir as Pendant</title></titleGroup><creators><creator xml:id="au1" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Xia</givenNames><familyName>Li</familyName></personName></creator><creator xml:id="au2" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Qi</givenNames><familyName>Wu</familyName></personName></creator><creator xml:id="au3" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Fu</givenNames><familyName>Zhang</familyName></personName></creator><creator xml:id="au4" creatorRole="author" affiliationRef="#af1" corresponding="yes"><personName><givenNames>Xian‐Fu</givenNames><familyName>Lin</familyName></personName><contactDetails><email>llc123@zju.edu.cn</email></contactDetails></creator></creators><affiliationGroup><affiliation xml:id="af1" countryCode="CN" type="organization"><unparsedAffiliation>Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China</unparsedAffiliation></affiliation></affiliationGroup><keywordGroup xml:lang="en" type="author"><keyword xml:id="kwd1">drug delivery systems</keyword><keyword xml:id="kwd2">enzymes</keyword><keyword xml:id="kwd3">copolymerization</keyword><keyword xml:id="kwd4">acyclovir</keyword></keywordGroup><fundingInfo><fundingAgency>National Natural Science Foundation of China</fundingAgency><fundingNumber>20474056</fundingNumber></fundingInfo><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p>An efficient protocol for the synthesis of functional polymeric prodrugs of acyclovir with variable copolymer composition and potential liver‐targeting delivery was achieved by combining enzymatic selective synthesis of polymerizable acyclovir derivatives with radical copolymerization of properly selected comonomers. Vinyl <sc>D</sc>‐galactose ester (VAG), acrylic acid (AA), and methyl methacrylate (MMA) were chosen as comonomers and three novel polymeric prodrugs with acyclovir as pendant were synthesized using 2,2′‐azo‐bis‐iso‐butyronitrile (AIBN) as initiator in <i>N</i>,<i>N</i>‐dimethylformamide (DMF). The resulting polymers were characterized by FTIR, NMR, and GPC. The influence of the concentration of initiator and the molar ratio of comonomers on the polymerization was investigated. <i>In vitro</i> drug release studies showed that acyclovir could be released from poly(2‐<i>N</i>‐vinylsebacyl‐acyclovir‐<i>co</i>‐methyl methacrylate) (poly(VSA‐<i>co</i>‐MMA)), and the total released acyclovir after 7 days in buffer solution at pH 1.2 and 7.4 was ∼ 35% and 29%, respectively. Also, homopolymers of vinyl acyclovir derivatives with high drug payload (>50 wt %) were obtained and characterized by the same methods. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2008</p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Chemoenzymatic synthesis, characterization, and controlled release of functional polymeric prodrugs with acyclovir as pendant</title></titleInfo><titleInfo type="abbreviated" lang="en"><title>Polymeric Prodrugs with Acyclovir as Pendant</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Chemoenzymatic synthesis, characterization, and controlled release of functional polymeric prodrugs with acyclovir as pendant</title></titleInfo><name type="personal"><namePart type="given">Xia</namePart><namePart type="family">Li</namePart><affiliation>Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Qi</namePart><namePart type="family">Wu</namePart><affiliation>Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Fu</namePart><namePart type="family">Zhang</namePart><affiliation>Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Xian‐Fu</namePart><namePart type="family">Lin</namePart><affiliation>Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China</affiliation><affiliation>E-mail: llc123@zju.edu.cn</affiliation><affiliation>Correspondence address: Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China===</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="article" displayLabel="article" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-6N5SZHKN-D">article</genre><originInfo><publisher>Wiley Subscription Services, Inc., A Wiley Company</publisher><place><placeTerm type="text">Hoboken</placeTerm></place><dateIssued encoding="w3cdtf">2008-04-05</dateIssued><dateCaptured encoding="w3cdtf">2007-03-10</dateCaptured><dateValid encoding="w3cdtf">2007-09-01</dateValid><copyrightDate encoding="w3cdtf">2008</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><extent unit="figures">5</extent><extent unit="tables">1</extent><extent unit="references">33</extent><extent unit="words">3986</extent></physicalDescription><abstract lang="en">An efficient protocol for the synthesis of functional polymeric prodrugs of acyclovir with variable copolymer composition and potential liver‐targeting delivery was achieved by combining enzymatic selective synthesis of polymerizable acyclovir derivatives with radical copolymerization of properly selected comonomers. Vinyl D‐galactose ester (VAG), acrylic acid (AA), and methyl methacrylate (MMA) were chosen as comonomers and three novel polymeric prodrugs with acyclovir as pendant were synthesized using 2,2′‐azo‐bis‐iso‐butyronitrile (AIBN) as initiator in N,N‐dimethylformamide (DMF). The resulting polymers were characterized by FTIR, NMR, and GPC. The influence of the concentration of initiator and the molar ratio of comonomers on the polymerization was investigated. In vitro drug release studies showed that acyclovir could be released from poly(2‐N‐vinylsebacyl‐acyclovir‐co‐methyl methacrylate) (poly(VSA‐co‐MMA)), and the total released acyclovir after 7 days in buffer solution at pH 1.2 and 7.4 was ∼ 35% and 29%, respectively. Also, homopolymers of vinyl acyclovir derivatives with high drug payload (>50 wt %) were obtained and characterized by the same methods. © 2007 Wiley Periodicals, Inc. 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