biodegradable synthetic polymers preparation, functionalization and application

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Engineering, Mechanics, Polymer, Medicine.Biomedical applications of diverse polymer in the medical industry

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  • Progress in Polymer Science 37 (2012) 237 280

    Contents lists available at ScienceDirect

    Progress in Polymer Science

    j ourna l ho me pag e: ww w.elsev ier .com/ locate /ppolysc i

    Biodegradable synthetic polymers: Preparation, functionalization andbiomedical application

    Huayu Tian, Zhaohui Tang, Xiuli Zhuang, Xuesi Chen , Xiabin JingKey Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022,China

    a r t i c l e i n f o

    Article history:Received 8 November 2009Received in revised form 14 May 2011Accepted 30 June 2011Available online 18 July 2011

    Keywords:BiodegradableSynthetic polymersFunctionalizationBiomedical application

    a b s t r a c t

    Biodegradable polymers have been widely used and have greatly promoted the devel-opment of biomedical elds because of their biocompatibility and biodegradability. Thedevelopment of biotechnology and medical technology has set higher requirements forbiomedical materials. Novel biodegradable polymers with specic properties are in greatdemand. Biodegradable polymers can be classied as natural or synthetic polymers accord-ing to the source. Synthetic biodegradable polymers have found more versatile and diversebiomedical applications owing to their tailorable designs or modications. This reviewpresents a comprehensive introduction to various types of synthetic biodegradable poly-mers with reactive groups and bioactive groups, and further describes their structure,preparation procedures and properties. The focus is on advances in the past decade in func-tionalization and responsive strategies of biodegradable polymers and their biomedical

    CorresponE-mail add

    AbbreviationPNIPAM; ASGatom-transferBECP, biodegranhydride; BTcell penetratintomography; Dtetraazacycloddocetaxel; EGpoly(ethyleneN-hydroxylethalanine; LCSTPLLA; MAL-PEmono-4-methdoped superpmPEG, poly(eN-hydroxysucP(GA-co-BLG)allylated PBLGlated PBLG; PPEI, polyethypoly(glutamicPEG-b-PLA-b-P(Asp-Hyd-ADmono- and di

    0079-6700/$ doi:10.1016/j.applications. The possible future developments of the materials are also discussed. 2011 Elsevier Ltd. All rights reserved.

    ding author. Tel.: +86 431 85262112; fax: +86 431 85262112.ress: xschen@ciac.jl.cn (X. Chen).s: ADR, adriamycin; AP, 1,5-diamino pentane; APEG-DOX, polyacetal-doxorubicin; Apt, aptamers; AS-PNIPAM, amino-semitelechelicPR, asialoglycoprotein receptor; ATQD, N-(4-aminophenyl)-N-(4-(3-triethoxysilyl-propyl-ureido) phenyl-1,4-quinonenediimine); ATRP,

    radical polymerization; BAA-NCA, -benzyl aspartic acid N-carboxy-anhydride; BMPCL, -(2-bromo-2-methyl propionyl)--caprolactone;adable electrically conducting polymer; BLA-NCA, benzyl-l-aspartate N-carboxyanhydride; BLG-NCA, -benzyl l-glutamate N-carboxy-MC, 5-benzyloxy-trimethylene carbonate; CaB, cathepsin B; CaD, cathepsin D; CMMPL, -chloromethyl--methyl--propionolactone; CPP,g peptide; c(RGDfK)-PEG-b-P(Lys-MP), c(RGDfK)-poly(ethylene glycol)-b-poly[-(3-mercaptopropino nyl)-lysine]; CT, computerized axialES, drug-eluting stents; DGBE, diethylene glycol bis(3-amino propyl) ether; DMSO, dimethyl sulfoxide; DOTA, designed macrocyclic 1,4,7,10-odecane-N,N ,N ,N -tetraacetic acid; DOX, doxorubicin; DPT, dipropylene triamine; DTPA-Gd, diethylenetriaminepentaacetic acid Gd; Dtxl,FR, endothelial growth factor receptor; EPR, enhanced permeability and retention; FOL, folic acid; gal-PEG-b-PBLG, galactose-conjugated

    glycol)-co-poly(-benzyl l-glutamate) block copolymer; Gd, gadolinium; GSH, glutathione; HEMA, 2-Hydroxyethylmethacrylate; HEMI,ylmaleimide; HO-R1-OH, di-hydroxyl compounds; ICG, indocyanine green; IgG, immunoglobulin G; l-DOPA, l-3,4-dihydroxyphenyl-l-

    , lower critical solution temperature; LP-NCA, l-phenylalanine NCA; M-PCL, maleimido-terminated PCL; M-PLLA, maleimido-terminatedG-PCL, maleimide-terminated poly(ethylene glycol)-poly(-caprolactone); MBC, 5-methyl-5-benzyloxycarbonyl-1,3-dioxan-2-one; MBPEC,oxybenzylidene-pentaerythritol carbonate; MMP-2, matrix metalloprotease-2; MMPs, matrix metalloproteinases; Mn-SPIO, manganesearamagnetic iron oxide; MP, 4-(3-aminopropyl) morpholine; MP-g-OEI, multi-armed poly(l-glutamic acid)-graft-oligoethylenimine;thylene glycol) methyl ether; MRI, magnetic resonance imaging; NCA, N-carboxy-anhydride; NGF, neurotrophic growth factors; NHS,cinimide; NIPAM, N-isopropylacrylamide; NIR, near-infrared; NIRF, near-infrared uorescent; NSCLC, non-small cell lung cancer;, poly[(l-glutamic acid)-co-(-benzyl l-glutamate)]; PAGA, poly(-(4-aminobutyl)-l-glycolic acid); PArg, polyarginine; PBALG, partially; PBCLG, partially chlorinated PBLG; PBLG, poly(-benzyl-l-glutamate); PBN3LG, partially azidized PBLG; PBPLG, partially propargy-py, polypyrrole; PCL, poly(-caprolactone); PCL-b-PBLG, poly(-caprolactone)-b-poly(-benzyl l-glutamate); PDI, polydispersity index;lenimine; PEG, polyethylene glycol; PEG-b-PEI, poly(ethylene glycol)-b-polyethyleneimine; PEG-b-P(Glu-DP), poly(ethylene glycol)-b-

    acid); PEG-b-P(LA-co-MCC/dtxel), poly(ethylene glycol)-block-poly(l-lactide-co-2-methyl-2-carboxyl-propylene carbonate/docetaxel;PLG, poly(ethyl glycol)-b-polylactide-b-poly(l-glutamic acid); PEG-P(Asp-Hyd), poly(ethylene glycol)-b-poly(aspartate-hydra zone); PEG-R), poly(ethylene glycol)-b-poly(aspartate-hydrazone-adriamycin); PEG-PBLA, poly(ethylene glycol)-poly(-benzyl-l-aspartate); PEGnLSer,ethyleneglycol modied PLSer; PET, positron emission tomography; PGS, planar gamma scintigraphy; PHB, poly[(R)-3-hydroxybutyrate];

    see front matter 2011 Elsevier Ltd. All rights reserved.progpolymsci.2011.06.004

  • 238 H. Tian et al. / Progress in Polymer Science 37 (2012) 237 280

    Contents

    1. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2392. Biopolymers with reactive groups . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 239

    2.1. Aliphatic polyesters . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2392.1.1. Aliphatic polyesters with carboxyl groups. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2392.1.2. Aliphatic polyesters with amino groups . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2392.1.3. Aliphatic polyesters with chloride groups . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2392.1.4. Aliphatic polyesters with keto or hydroxyl groups . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2402.1.5. Aliphatic polyesters with bromide groups . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2402.1.6. Aliphatic polyesters with C C groups . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2402.1.7. Aliphatic polyesters with reactive groups by copolymerization . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 240

    2.2. Polycarbonate . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2412.3. Poly(amino acids) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 246

    2.3.1. Poly(acidic amino acids) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2462.3.2. Poly(basic amino acid) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2502.3.3. Poly(neutral amino acid) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 252

    2.4. Polyphosphoesters . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

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