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Chemoenzymatic synthesis, characterization, and controlled release of functional polymeric prodrugs with acyclovir as pendant

Identifieur interne : 000F02 ( Istex/Corpus ); précédent : 000F01; suivant : 000F03

Chemoenzymatic synthesis, characterization, and controlled release of functional polymeric prodrugs with acyclovir as pendant

Auteurs : Xia Li ; Qi Wu ; Fu Zhang ; Xian-Fu Lin

Source :

RBID : ISTEX:24ADC09FD9E9A0100172235576F3CD611287A647

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

Url:
DOI: 10.1002/app.27680

Links to Exploration step

ISTEX:24ADC09FD9E9A0100172235576F3CD611287A647

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<title type="main" xml:lang="en">Chemoenzymatic synthesis, characterization, and controlled release of functional polymeric prodrugs with acyclovir as pendant</title>
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<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>
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<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. J Appl Polym Sci, 2008</abstract>
<note type="funding">National Natural Science Foundation of China - No. 20474056; </note>
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