Functionally Modified Hyperbranched Polyglycerols for Drug Delivery

doi:10.11944/j.issn.1000-0518.2015.04.140246

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (4): 367-378.DOI: 10.11944/j.issn.1000-0518.2015.04.140246

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Functionally Modified Hyperbranched Polyglycerols for Drug Delivery

ZHANG Yi, WU Lingbo, HU Qian, CHEN Baoxin, Wu Boyang, XUE Wei^*

Key Laboratory of Biomaterials of Guangdong Higher Education Institutes,Department of Biomedical Engineering,Ji'nan University,Guangzhou 510632,China

Received:2014-07-16 Revised:2014-10-16 Published:2015-04-10 Online:2015-04-10
Contact: XUE Wei, professor; Tel/Fax:020-85224338; E-mail:weixue_jnu@hotmail.com; Research interests:biomaterials, drug delivery
Supported by:
Supported by the National Natural Science Foundation of China(No.81101151, No.31271019)

Abstract

Abstract: Polymeric nanocarriers with controllable drug realease and stimuli-responsive to targeted biological conditions are an advancing and potential carrier candidate for nanomedicines. Hyperbranched polyglycerols (HPG) spur the interest of the biomaterial community due to their well-defined three-dimensional structures, good solubility, high biocompatiblity and multiple attachment sites for modification. Functionally modified HPG derivatives are able to self-assemble into a variety of drug carriers such as micelles and vesicles. Herein, we present the current progress on functional modified HPG for drug delivery with particular focus on amphiphilic modification, stimuli-responsive functionalization, as well as supramolecular self-assembly. Molecular design strategy for HPG modification with amphiphilic and stimuli responsive functionalization is systematically summarized. Furthermore, the assembly behavior of hyperbranched supramolecular polyglycerol copolymers based on cyclodextrin host-guest interactions is also mentioned.

Key words: hyperbranched polyglycerol, drug delivery, amphiphilic modification, stimuli responsive, supramolecular self-assembl

CLC Number:

O632
TB324

ZHANG Yi, WU Lingbo, HU Qian, CHEN Baoxin, Wu Boyang, XUE Wei . Functionally Modified Hyperbranched Polyglycerols for Drug Delivery[J]. Chinese Journal of Applied Chemistry, 2015, 32(4): 367-378.

References

[1] Tomalia D A,Baker H,Dewald J, et al . A new Class of Polymers:Starburst-Dendritic Macromolecules[J]. Polym J ,1985,17(1):117-132.
[2] Inoue K. Functional Dendrimers,Hyperbranched and Star Polymers[J]. Prog Polym Sci ,2000,25(4):453-571.
[3] Jikei M,Kakimoto M. Hyperbranched Polymers:A Promising New Class of Materials[J]. Prog Polym Sci ,2001,26(8):1233-1285.
[4] Gao C,Yan D. Hyperbranched Polymers:From Synthesis to Applications[J]. Prog Polym Sci ,2004,29(3):183-275.
[5] Kim Y H,Webster O W. Hyperbranched Polyphenylenes[J]. Macromolecules ,1992,25(21): 5561-5572.
[6] Wilms D,Stiriba S E,Frey H. Hyperbranched Polyglycerols:From the Controlled Synthesis of Biocompatible Polyether Polyols to Multipurpose Applications[J]. Acc Chem Res ,2010,43(1):129-141.
[7] Calderon M,Quadir M A,Sharma SK, et al . Dendritic Polyglycerols for Biomedical Applications[J]. Adv Mater ,2010,22(2):190-218.
[8] Kainthan R K,Hester S R,Levin E, et al . In Vitro Biological Evaluation of High Molecular Weight Hyperbranched Polyglycerols[J]. Biomaterials ,2007,28(31):4581-4590.
[9] Kainthan R K,Brooks D E. In Vivo Biological Evaluation of High Molecular Weight Hyperbranched Polyglycerols[J]. Biomaterials ,2007,28(32):4779-4787.
[10] Imran ul-haq M,Lai B F,Chapanian R, et al . Influence of Architecture of High Molecular Weight Linear and Branched Polyglycerols on Their Biocompatibility and Biodistribution[J]. Biomaterials ,2012,33(35):9135-9147.
[11] Gupta U,Agashe H B,Asthana A, et al . Dendrimers: Novel Polymeric Nanoarchitectures for Solubility Enhancement[J]. Biomacromolecules ,2006,7(3):649-658.
[12] Jin H B,Huang W,Zhu X Y, et al . Biocompatible or Biodegradable Hyperbranched Polymers:From Self-assembly to Cytomimetic Applications[J]. Chem Soc Rev ,2012,41(18):5986-5997.
[13] Cheng H X,Wang S G,Yang J T, et al . Synthesis and Self-assembly of Amphiphilic Hyperbranched Polyglycerols Modified with Palmitoyl Chloride[J]. J Colloid Interf Sci ,2009,337(1):278-284.
[14] Burgath A,Sunder A,Neuner I, et al . Multi-arm Star Block Copolymers Based on Epsilon-Caprolactone with Hyperbranched Polyglycerol Core[J]. Macromol Chem Phys ,2000,201(7):792-797.
[15] Knischka R,Lutz P J,Sunder A, et al . Functional Poly(ethylene oxide) Multiarm Star Polymers:Core-First Synthesis Using Hyperbranched Polyglycerol Initiators[J]. Macromolecules ,2000,33(2):315-320.
[16] Sunder A,Mulhaupt R,Frey H. Hyperbranched Polyether-Polyols Based on Polyglycerol:Polarity Design by Block Copolymerization with Propylene Oxide[J]. Macromolecules ,2000,33(2):309-314.
[17] Sunder A,Kramer M,Hanselmann R, et al . Molecular Nanocapsules Based on Amphiphilic Hyperbranched Polyglycerols[J]. Angew Chem Int Edit ,1999,38(23):3552-3555.
[18] Oikawa Y,Lee S,Kim D H, et al .One-Pot Synthesis of Linear-Hyperbranched Amphiphilic Block Copolymers Based on Polyglycerol Derivatives and Their Micelles[J]. Biomacromolecules ,2013,14(7):2171-2178.
[19] Kurniasih IN,Liang H,Kumar S, et al . A Bifunctional Nanocarrier Based on Amphiphilic Hyperbranched Polyglycerol Derivatives[J]. J Mater Chem B ,2013,1(29):3569-3577.
[20] Turk H,Shukla A,Rodrigues PCA, et al . Water-Soluble Dendritic Core-Shell-Type Architectures Based on Polyglycerol for Solubilization of Hydrophobic Drugs[J]. Chem-Eur J ,2007,13(15):4187-4196.
[21] Zhang XJ,Zhang XG,Yu PE, et al . Hydrotropic Polymeric Mixed Micelles Based on Functional Hyperbranched Polyglycerol Copolymers as Hepatoma-Targeting Drug Delivery System[J]. J Pharm Sci-US ,2013,102(1):145-153.
[22] Kainthan R K,Mugabe C,Burt H M, et al . Unimolecular Micelles Based on Hydrophobically Derivatized Hyperbranched Polyglycerols:Ligand Binding Properties[J]. Biomacromolecules ,2008,9(3):886-895.
[23] Kainthan R K,Brooks D E. Unimolecular Micelles based on Hydrophobically Derivatized Hyperbranched Polyglycerols:Biodistribution Studies[J]. Bioconjug Chem ,2008,19(11):2231-2238.
[24] Mugabe C,Hadaschik B A,Kainthan R K, et al . Paclitaxel Incorporated in Hydrophobically Derivatized Hyperbranched Polyglycerols for Intravesical Bladder Cancer Therapy[J]. BJU Int ,2009,103(7):978-986.
[25] Kumar S,Mohr A,Kumar A, et al . Synthesis of Biodegradable Amphiphilic Nanocarriers by Chemo-Enzymatic Transformations for the Solubilization of Hydrophobic Compounds[J]. Int J Artif Organs ,2011,34(2):84-92.
[26] Zhang XJ,Zhang XG,Wu ZM, et al . A Hydrotropic Beta-Cyclodextrin Grafted Hyperbranched Polyglycerol co-Polymer for Hydrophobic Drug Delivery[J]. Acta Biomater ,2011,7(2):585-592.
[27] Zhang XJ,Zhang XE,Wu ZM, et al . beta-Cyclodextrin Grafting Hyperbranched Polyglycerols as Carriers for Nasal Insulin Delivery[J]. Carbohydr Polym ,2011,84(4):1419-1425.
[28] Popeney C S,Lukowiak M C,Bottcher C, et al . Tandem Coordination, Ring-Opening, Hyperbranched Polymerization for the Synthesis of Water-Soluble Core-Shell Unimolecular Transporters[J]. ACS Macro Lett ,2012,1(5):564-567.
[29] Han Y,Gao C. Miktoarms hyperbranched polymer brushes: One-Step Fast Synthesis by Parallel Click Chemistry and Hierarchical Self-Assembly[J]. Sci China Chem ,2010,53(12):2461-2471.
[30] Kuchler S,Radowski M R,Blaschke T, et al . Nanoparticles for Skin Penetration Enhancement - A Comparison of a Dendritic Core-Multishell-Nanotransporter and Solid Lipid Nanoparticles[J]. Eur J Pharm Biopharm ,2009,71(2):243-250.
[31] Radowski M R,Shukla A,von Berlepsch H, et al . Supramolecular Aggregates of Dendritic Multishell Architectures as Universal Nanocarriers[J]. Angew Chem Int Edit ,2007,46(8):1265-1269.
[32] Burakowska E,Haag R. Dendritic Polyglycerol Core-Double-Shell Architectures: Synthesis and Transport Properties[J]. Macromolecules ,2009,42(15):5545-5550.
[33] Gao X J,Zhang X E,Wu Z M, et al . Synthesis and Physicochemical Characterization of a Novel Amphiphilic Polylactic Acid-Hyperbranched Polyglycerol Conjugate for Protein Delivery[J]. J Control Release ,2009,140(2):141-147.
[34] Hu M,Chen M S,Li G L, et al . Biodegradable Hyperbranched Polyglycerol with Ester Linkages for Drug Delivery[J]. Biomacromolecules ,2012,13(11):3552-3561.
[35] Shenoi R A,Lai B F L,Ul-Haq M I, et al . Biodegradable Polyglycerols with Randomly Distributed Ketal Groups as Multi-Functional Drug Delivery Systems[J]. Biomaterials ,2013,34(25):6068-6081.
[36] Fleige E,Quadir M A,Haag R. Stimuli-Responsive Polymeric Nanocarriers for the Controlled Transport of Active Compounds:Concepts and Applications[J]. Adv Drug Deliver Rev ,2012,64(9):866-884.
[37] Kolhe P,Khandare J,Pillai O, et al .Hyperbranched Polymer-Drug Conjugates with High Drug Payload for Enhanced Cellular Delivery[J]. Pharm Res ,2004,21(12):2185-2195.
[38] Calderon M,Graeser R,Kratz F, et al . Development of Enzymatically Cleavable Prodrugs Derived from Dendritic Polyglycerol[J]. Bioorg Med Chem Lett ,2009,19(14):3725-3728.
[39] Calderon M,Welker P,Licha K, et al . Development of Efficient Acid Cleavable Multifunctional Prodrugs Derived from Dendritic Polyglycerol with a Poly(ethylene glycol) Shell[J]. J Control Release ,2011,151(3):295-301.
[40] Zhang X J,Achazi K,Steinhilber D, et al . A Facile Approach for Dual-Responsive Prodrug Nanogels Based on Dendritic Polyglycerols with Minimal Leaching[J]. J Control Release ,2014,174:209-216.
[41] Cao L C,Mou M,Wang Y C. Hyperbranched and Viologen-Functionalized Polyglycerols: Preparation, Photo- and Electrochromic Performance[J]. J Mater Chem ,2009,19(21):3412-3418.
[42] Xu S J,Luo Y,Graeser R, et al . Development of pH-responsive Core-Shell Nanocarriers for Delivery of Therapeutic and Diagnostic Agents[J]. Bioorg Med Chem Lett ,2009,19(3):1030-1034.
[43] Burakowska E,Zimmerman S C,Haag R. Photoresponsive Crosslinked Hyperbranched Polyglycerols as Smart Nanocarriers for Guest Binding and Controlled Release[J]. Small ,2009,5(19):2199-2204.
[44] Sun X Y,Zhou Y F,Yan D Y. Drug Release Property of a pH-responsive Double-Hydrophilic Hyperbranched Graft Copolymer[J]. Sci China Ser B ,2009,52(10):1703-1710.
[45] Kojima C,Yoshimura K,Harada A, et al . Synthesis and Characterization of Hyperbranched Poly(glycidol) Modified with pH- and Temperature-Sensitive Groups[J]. Bioconjug Chem ,2009,20(5):1054-1057.
[46] Taylor D K,Jayes F L,House A J, et al . Temperature-Responsive Biocompatible Copolymers Incorporating Hyperbranched Polyglycerols for Adjustable Functionality[J]. J Funct Biomater ,2011,2(3):173-194.
[47] Han G,You C C,Kim B J, et al . Light-Regulated Release of DNA and Its Delivery to Nuclei by Means of Photolabile Gold Nanoparticles[J]. Angew Chem Int Edit ,2006,45(19):3165-3169.
[48] Nishiyama N,Iriyama A,Jang W D, et al . Light-Induced Gene Transfer from Packaged DNA Enveloped in a Dendrimeric Photosensitizer[J]. Nat Mater ,2005,4(12):934-941.
[49] Han Y,Gao C,He X H. Reversible Photoswitching Self-assembly of Azobenzene-Functionalized Hyperbranched Polyglycerol Induced by Host-Guest Chemistry[J]. Sci China Chem ,2012,55(4):604-611.
[50] Steinhilber D,Sisson A L,Mangoldt D, et al .Synthesis, Reductive Cleavage, and Cellular Interaction Studies of Biodegradable, Polyglycerol Nanogels[J]. Adv Funct Mater ,2010,20(23):4133-4138.
[51] Fischer W,Calderon M,Schulz A, et al . Dendritic Polyglycerols with Oligoamine Shells Show Low Toxicity and High siRNA Transfection Efficiency in Vitro [J]. Bioconjug Chem ,2010,21(10):1744-1752.
[52] Zhao L,Chano T,Morikawa S, et al . Hyperbranched Polyglycerol-Grafted Superparamagnetic Iron Oxide Nanoparticles:Synthesis, Characterization, Functionalization, Size Separation, Magnetic Properties, and Biological Applications[J]. Adv Funct Mater ,2012,22(24):5107-5117.
[53] Adeli M,Fard A K,Abedi F, et al . Thermo- and pH-Sensitive Dendrosomes as Bi-phase Drug Delivery Systems[J]. Nanomed-Nanotechnol ,2013,9(8):1203-1213.
[54] Fustin C A,Guillet P,Schubert U S, et al . Metallo-Supramolecular Block Copolymers[J]. Adv Mater ,2007,19(13):1665-1673.
[55] Moughton A O,O'Reilly R K. Using Metallo-Supramolecular Block Copolymers for the Synthesis of Higher Order Nanostructured Assemblies[J]. Macromol Rapid Comm ,2010,31(1):37-52.
[56] Zhou Y,Yan D. Supramolecular Self-assembly of Amphiphilic Hyperbranched Polymers at all Scales and Dimensions:Progress, Characteristics and Perspectives[J]. Chem Commun ,2009,(10):1172-1188.
[57] Tao W,Liu Y,Jiang B B, et al . A Linear-Hyperbranched Supramolecular Amphiphile and Its Self-Assembly into Vesicles with Great Ductility[J]. J Am Chem Soc ,2012,134(2):762-764.
[58] Liu Y,Yu C Y,Jin H B, et al . A Supramolecular Janus Hyperbranched Polymer and Its Photoresponsive Self-Assembly of Vesicles with Narrow Size Distribution[J]. J Am Chem Soc ,2013,135(12):4765-4770.

Functionally Modified Hyperbranched Polyglycerols for Drug Delivery

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