聚乳酸两亲性共聚物的研究进展
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摘要
聚乳酸是一种具有良好的生物相容性和可降解性高分子材料,也是被美国食品和药品管理局(FDA)批准的生物医用材料.但它本身的疏水性使其在医用方面受到限制.为克服其缺陷,人们对聚乳酸做了大量改性修饰的工作以提高亲水性,如将其与各种亲水性聚合物进行聚合制得不同结构类型的两亲性共聚物.本文中我们对聚乳酸两亲性共聚物的研究进展做了综述,并讨论了它的应用现状及前景.
Polylactic acid(PLA)is an excellent polymer material with good properties of biocompatibility and biodegradation,and is also approved as biomedical materials by Food and Drug Administration(FDA)of the United States.But its application in medical material is limited because of its hydrophobicity.In order to enhance its hydrophilicity,PLA has been modificated,for example PLA copolymerized with hydrophilic polymers to produce different types of amphiphilic copolymers.In this article,the research progress of amphiphilic copolymers of polyactic acid is reviewed,and its status and prospects of application are discussed.
Polylactic acid(PLA)is an excellent polymer material with good properties of biocompatibility and biodegradation,and is also approved as biomedical materials by Food and Drug Administration(FDA)of the United States.But its application in medical material is limited because of its hydrophobicity.In order to enhance its hydrophilicity,PLA has been modificated,for example PLA copolymerized with hydrophilic polymers to produce different types of amphiphilic copolymers.In this article,the research progress of amphiphilic copolymers of polyactic acid is reviewed,and its status and prospects of application are discussed.
引文
[1]路德待,张小伟,周添红,等.可降解乳酸共聚物[J].化学进展,2008,20(2):339-350.
[2]程蓉,钱欣.聚乳酸的改性及应用进展[J].化工进展,2002,21(11):824-826.
[3]GOPFERICH A,PETER S J,LUCKE A,et al.Modulation of marrow stromal cell function using poly(D,Llactic acid)-block-poly(ethylene glycol)-monomethyl ether surfaces[J].J Bio Mater Res,1999,46(3):390-398.
[4]宋继彬.α-氨基聚乙二醇-聚乳酸嵌段共聚物的合成(α-H2N-PEG-b-PLA)的合成及其医用研究[D].济南:山东大学,2010:1-2.
[5]WU Q H,YI J,WANG S Y,et al.Synthesis and selfassembly of new amphiphilic thermosensitive poly(N-vinylcaprolactam)/poly(D,L-lactide)block copolymers via the combination of ring-opening polymerization and click chemistry[J].Polym Bull,2015,72(6):1449-1466.
[6]TUCKING K S,GRUETZNER V,UNGER R E,et al.Dual enzyme-responsive capsules of hyaluronic acidblock-poly(Lactic Acid)for sensing bacterial enzymes[J].Macro Rap Comm,2015,36(13):1248-1254.
[7]ABEBE D G,KANDIL R,KRAUS T,et al.ThreeLayered biodegradable micelles prepared by two-step self-assembly of PLA-PEI-PLA and PLA-PEG-PLA triblock copolymers as efficient gene delivery system[J].Macromol Biosci,2015,15(5):689-711.
[8]GANG R,SI S F.Preparation and characterization of poly(lacticacid)-poly(ethylene glycol)-poly(lactic acid)(PLA-PEG-PLA)m icrospheres for controlled release of paclitaxel[J].Biomaterials,2003,24(27):5037-5044.
[9]YANG Q L,HE C Y,ZHANG Z,et al.Redox-responsive flower-like micelles of poly(L-lactic acid)-bpoly(ethylene glycol)-b-poly(L-lactic acid)for intracellular drug delivery[J].Polymer,2016,90:351-362.
[10]LI C Y,LIU X L,HE S S,et al.Synthesis and AIE properties of PEG-PLA-PMPC based triblock amphiphilic biodegradable polymers[J].Polym Chem,2016,7(5):1121-1126.
[11]李晓然,袁晓燕.聚乙二醇-聚乳酸共聚物药物载体[J].化学进展,2007,19(6):973-981.
[12]CRAPARO E F,LICCIARDI M,CONIGLIARO A,et al.Hepatocyte-targeted fluorescent nanoparticles based on a polyaspartamide for potential theranostic applications[J].Polymer,2015,70:257-270.
[13]LUO J,GIGUERE G,ZHU X.Asymmetric poly(ethylene glycol)star polymers with a cholic acid core and their aggregation properties[J].Biomacromolecules,2009,10(4):900-906.
[14]SALAAM L E,DEAN D,BRAY T L.In vitro degradation behavior of biodegradable 4-star micelles[J].Polymer,2006,47:310-318.
[15]LU D D,YUAN J C,LI H G,et al.Synthesis and characterization of a series of biodegradable and biocompatible PEG-supported poly(lactic-ran-glycolic acid)amphiphilic barbell-like copolymers[J].J Polym Sci Part A,2008,46(11):3802-3812.
[16]HU M Y,SHEN Y R,ZHANG L,et al.Polymersomes via self-assembly of amphiphilic beta-cyclodextrin-centered triarm star polymers for enhanced oral bioavailability of water-soluble chemotherapeutics[J].Biomacromolecules,2016,17(3):1026-1039.
[17]PAN J,SUBBUS,FENG M,et al.Micelle-like nanoparticles of star-branched PEO-PLA copolymers as chemotherapeutic carrier[J].Control Release,2005,110(1):20-33.
[18]张安强,林雅铃,魏芬芬,等.星形聚乙二醇-聚乳酸嵌段共聚物的合成与表征[J].高分子材料科学与工程,2011,27(11):83-88.
[19]JAIN J P,KUMAR N.Self-assembly of amphiphilic(PEG)3-PLA copolymer as polymersomes:preparation,characterization,and their evaluation as drug carrier[J].Biomacromolecules,2010,11(4):1027-1035.
[20]KIM Y S,GIL E S,LOWE T L.Synthesis and characterization of thermoresponsive-co-biodegradable lineardendritic copolymers[J].Macromolecules,2006,39(23):7805-7811.
[21]FAN X S,WANG Z,YUAN D,et al.Novel lineardendritic-like amphiphilic copolymers:synthesis and self-assembly characteristics[J].Polym Chem,2014,5:4069-4075.
[22]CAO W Q,ZHU L.Synthesis and unimolecular micelles of amphiphilic dendrimer-like star polymer with various functional surface groups[J].Macromolecules,2011,44(6):1500-1512.
[23]GONG F R,CHENG X Y,WANG S F,et al.Biodegradable comb-dendritic tri-block copolymers consisting of poly(ethylene glycol)and poly(L-lactide):synthesis,characterizations,and regulation of surface morphology and cell responses[J].Polymer,2009,50(13):2775-2785.
[24]FAN X S,HU Z G,WANG G W.Synthesis and unimolecular micelles of amphiphiliccopolymer with dendritic poly(L-lactide)core and poly(ethylene oxide)shell for drug delivery[J].RSC Adv,2015,5,100816-100823.
[25]SANDA F,FUJIYAMA T,ENDO T.Chemical synthesis of poly-γ-glutamic acid by polycondensation ofγ-glutamic acid dimer:synthesis and reaction of poly-γ-glutamic acid methyl ester[J].J Polym Sci,Part A,2001,39(5):732-741.
[26]刁建志,周炬,彭政.超支化聚合物应用研究进展[J].现代塑料加工应用,2008,20(6):55-58.
[27]YANG D,JENNIFER K S,CHRISTOPHER J H,et al.The effect of hyperbranched polyglycerol coatings on drug delivery using degradable polymer nanoparticles[J].Biomaterials,2014,35:6595-6602.
[28]LIU J Y,HUANG W,PANG Y,et al.Self-assembled micelles from an amphiphilic hyperbranched copolymer with polyphosphate arms for drug delivery[J].Langmuir,2010,26(13):10585-10592.
[29]郁志芳,朱康杰.一种两亲生物降解高分子-聚丙交酯-聚乙二醇嵌段共聚物的研究进展[J].功能高分子学报,2003,16:417-422.
[30]HARIHARAN S,BHARDWAJ V,BALA I,et al.Design of estradiol loaded PLGA nanoparticulate formulation:a potential oral delivery system for hormone therapy[J].Pharm Res,2006,23:184-195.
[31]LI Y P,PEI Y Y,ZHANG X Y,et al.PEGylated PLGA nanoparticles as proteincarriers:synthesis,preparation and biodistribution in rats[J].J Control Release,2001,71(2):203-211.
[32]TOBIO M,SANCHEZ A,VILA A,et al.The role of PEG on the stability in digestive fluids and in vivo fate of PEG-PLA nanoparticles following oral administration[J].Collo Sur Biointerfaces,2000,18:215-323.
[33]BAE Y H,HUH K M,KIM Y,et al.Biodegradable amphiphilic multiblock copolymers and their implications for biomedical applications[J].Control Release,2000,64:3-13.
[34]CHEN H Y,HE S S.PLA-PEG coated multifunctional imaging probe for targeted drug delivery[J].Pharmaceutics,2015,12(6):1885-1892.
[35]CUI H T,SHAO J,WANG Y,et al.PLA-PEGPLA and its electroactive tetraaniline copolymer as multi-interactive injectable hydrogels for tissue engineering[J].Biomacromolecules,2013,14(6):1904-1912.
[36]COUMES F,HUANG C Y,HUANG C H,et al.Design and development of immunomodulatory antigen delivery systems based on peptide/PEG-PLA conjugate for tuning immunity[J].Biomacromolecules,2015,16(11):3666-3673.
[37]WANG C H,HSIUE G H.New amphiphilic poly(2-ethyl-2-oxazoline)poly(L-lactide)triblock copolymer[J].Biomacromolecules,2003,4(6):1487-1490.
[2]程蓉,钱欣.聚乳酸的改性及应用进展[J].化工进展,2002,21(11):824-826.
[3]GOPFERICH A,PETER S J,LUCKE A,et al.Modulation of marrow stromal cell function using poly(D,Llactic acid)-block-poly(ethylene glycol)-monomethyl ether surfaces[J].J Bio Mater Res,1999,46(3):390-398.
[4]宋继彬.α-氨基聚乙二醇-聚乳酸嵌段共聚物的合成(α-H2N-PEG-b-PLA)的合成及其医用研究[D].济南:山东大学,2010:1-2.
[5]WU Q H,YI J,WANG S Y,et al.Synthesis and selfassembly of new amphiphilic thermosensitive poly(N-vinylcaprolactam)/poly(D,L-lactide)block copolymers via the combination of ring-opening polymerization and click chemistry[J].Polym Bull,2015,72(6):1449-1466.
[6]TUCKING K S,GRUETZNER V,UNGER R E,et al.Dual enzyme-responsive capsules of hyaluronic acidblock-poly(Lactic Acid)for sensing bacterial enzymes[J].Macro Rap Comm,2015,36(13):1248-1254.
[7]ABEBE D G,KANDIL R,KRAUS T,et al.ThreeLayered biodegradable micelles prepared by two-step self-assembly of PLA-PEI-PLA and PLA-PEG-PLA triblock copolymers as efficient gene delivery system[J].Macromol Biosci,2015,15(5):689-711.
[8]GANG R,SI S F.Preparation and characterization of poly(lacticacid)-poly(ethylene glycol)-poly(lactic acid)(PLA-PEG-PLA)m icrospheres for controlled release of paclitaxel[J].Biomaterials,2003,24(27):5037-5044.
[9]YANG Q L,HE C Y,ZHANG Z,et al.Redox-responsive flower-like micelles of poly(L-lactic acid)-bpoly(ethylene glycol)-b-poly(L-lactic acid)for intracellular drug delivery[J].Polymer,2016,90:351-362.
[10]LI C Y,LIU X L,HE S S,et al.Synthesis and AIE properties of PEG-PLA-PMPC based triblock amphiphilic biodegradable polymers[J].Polym Chem,2016,7(5):1121-1126.
[11]李晓然,袁晓燕.聚乙二醇-聚乳酸共聚物药物载体[J].化学进展,2007,19(6):973-981.
[12]CRAPARO E F,LICCIARDI M,CONIGLIARO A,et al.Hepatocyte-targeted fluorescent nanoparticles based on a polyaspartamide for potential theranostic applications[J].Polymer,2015,70:257-270.
[13]LUO J,GIGUERE G,ZHU X.Asymmetric poly(ethylene glycol)star polymers with a cholic acid core and their aggregation properties[J].Biomacromolecules,2009,10(4):900-906.
[14]SALAAM L E,DEAN D,BRAY T L.In vitro degradation behavior of biodegradable 4-star micelles[J].Polymer,2006,47:310-318.
[15]LU D D,YUAN J C,LI H G,et al.Synthesis and characterization of a series of biodegradable and biocompatible PEG-supported poly(lactic-ran-glycolic acid)amphiphilic barbell-like copolymers[J].J Polym Sci Part A,2008,46(11):3802-3812.
[16]HU M Y,SHEN Y R,ZHANG L,et al.Polymersomes via self-assembly of amphiphilic beta-cyclodextrin-centered triarm star polymers for enhanced oral bioavailability of water-soluble chemotherapeutics[J].Biomacromolecules,2016,17(3):1026-1039.
[17]PAN J,SUBBUS,FENG M,et al.Micelle-like nanoparticles of star-branched PEO-PLA copolymers as chemotherapeutic carrier[J].Control Release,2005,110(1):20-33.
[18]张安强,林雅铃,魏芬芬,等.星形聚乙二醇-聚乳酸嵌段共聚物的合成与表征[J].高分子材料科学与工程,2011,27(11):83-88.
[19]JAIN J P,KUMAR N.Self-assembly of amphiphilic(PEG)3-PLA copolymer as polymersomes:preparation,characterization,and their evaluation as drug carrier[J].Biomacromolecules,2010,11(4):1027-1035.
[20]KIM Y S,GIL E S,LOWE T L.Synthesis and characterization of thermoresponsive-co-biodegradable lineardendritic copolymers[J].Macromolecules,2006,39(23):7805-7811.
[21]FAN X S,WANG Z,YUAN D,et al.Novel lineardendritic-like amphiphilic copolymers:synthesis and self-assembly characteristics[J].Polym Chem,2014,5:4069-4075.
[22]CAO W Q,ZHU L.Synthesis and unimolecular micelles of amphiphilic dendrimer-like star polymer with various functional surface groups[J].Macromolecules,2011,44(6):1500-1512.
[23]GONG F R,CHENG X Y,WANG S F,et al.Biodegradable comb-dendritic tri-block copolymers consisting of poly(ethylene glycol)and poly(L-lactide):synthesis,characterizations,and regulation of surface morphology and cell responses[J].Polymer,2009,50(13):2775-2785.
[24]FAN X S,HU Z G,WANG G W.Synthesis and unimolecular micelles of amphiphiliccopolymer with dendritic poly(L-lactide)core and poly(ethylene oxide)shell for drug delivery[J].RSC Adv,2015,5,100816-100823.
[25]SANDA F,FUJIYAMA T,ENDO T.Chemical synthesis of poly-γ-glutamic acid by polycondensation ofγ-glutamic acid dimer:synthesis and reaction of poly-γ-glutamic acid methyl ester[J].J Polym Sci,Part A,2001,39(5):732-741.
[26]刁建志,周炬,彭政.超支化聚合物应用研究进展[J].现代塑料加工应用,2008,20(6):55-58.
[27]YANG D,JENNIFER K S,CHRISTOPHER J H,et al.The effect of hyperbranched polyglycerol coatings on drug delivery using degradable polymer nanoparticles[J].Biomaterials,2014,35:6595-6602.
[28]LIU J Y,HUANG W,PANG Y,et al.Self-assembled micelles from an amphiphilic hyperbranched copolymer with polyphosphate arms for drug delivery[J].Langmuir,2010,26(13):10585-10592.
[29]郁志芳,朱康杰.一种两亲生物降解高分子-聚丙交酯-聚乙二醇嵌段共聚物的研究进展[J].功能高分子学报,2003,16:417-422.
[30]HARIHARAN S,BHARDWAJ V,BALA I,et al.Design of estradiol loaded PLGA nanoparticulate formulation:a potential oral delivery system for hormone therapy[J].Pharm Res,2006,23:184-195.
[31]LI Y P,PEI Y Y,ZHANG X Y,et al.PEGylated PLGA nanoparticles as proteincarriers:synthesis,preparation and biodistribution in rats[J].J Control Release,2001,71(2):203-211.
[32]TOBIO M,SANCHEZ A,VILA A,et al.The role of PEG on the stability in digestive fluids and in vivo fate of PEG-PLA nanoparticles following oral administration[J].Collo Sur Biointerfaces,2000,18:215-323.
[33]BAE Y H,HUH K M,KIM Y,et al.Biodegradable amphiphilic multiblock copolymers and their implications for biomedical applications[J].Control Release,2000,64:3-13.
[34]CHEN H Y,HE S S.PLA-PEG coated multifunctional imaging probe for targeted drug delivery[J].Pharmaceutics,2015,12(6):1885-1892.
[35]CUI H T,SHAO J,WANG Y,et al.PLA-PEGPLA and its electroactive tetraaniline copolymer as multi-interactive injectable hydrogels for tissue engineering[J].Biomacromolecules,2013,14(6):1904-1912.
[36]COUMES F,HUANG C Y,HUANG C H,et al.Design and development of immunomodulatory antigen delivery systems based on peptide/PEG-PLA conjugate for tuning immunity[J].Biomacromolecules,2015,16(11):3666-3673.
[37]WANG C H,HSIUE G H.New amphiphilic poly(2-ethyl-2-oxazoline)poly(L-lactide)triblock copolymer[J].Biomacromolecules,2003,4(6):1487-1490.