Light-responsive azobenzene-based glycopolymer micelles for targeted drug delivery to melanoma cells

被引:54
作者
Pearson, Samuel [1 ]
Vitucci, Dylan [1 ]
Khine, Yee Yee [1 ]
Dag, Aydan [1 ,3 ]
Lu, Hongxu [1 ]
Save, Maud [2 ]
Billon, Laurent [2 ]
Stenzel, Martina H. [1 ]
机构
[1] Univ New S Wales, Sch Chem Engn, Ctr Adv Macromol Design, Sydney, NSW 2052, Australia
[2] Univ Pau & Pays Adour, EPCP, IPREM, UMR 5254, F-64053 Pau 09, France
[3] Bezmialem Vakif Univ, Dept Pharmaceut Chem, Fac Pharm, TR-34093 Istanbul, Turkey
基金
澳大利亚研究理事会;
关键词
Glycopolymers; Light-responsive; Micelle; Azo; Melanoma; CONTAINING DIBLOCK COPOLYMER; RAFT POLYMERIZATION; BLOCK-COPOLYMERS; SWITCHING SPEEDS; POLYMERS; BEHAVIOR; SYSTEMS; PHOTOISOMERIZATION; BIOMATERIALS; CONJUGATION;
D O I
10.1016/j.eurpolymj.2015.04.001
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Light-responsive glycopolymer micelles were produced by the self-assembly of amphiphilic block copolymers containing azobenzene and beta-galactose units. These well-defined block copolymers were synthesised firstly by the RAFT polymerisation of an azobenzene methacrylate monomer (AzoMA) to produce two short azobenzene macroRAFT agents containing 7 and 15 monomer units. Chain extension with a second block of similar to 150 or similar to 250 sugar units comprising of a protected beta-galactose monomer (beta-AcGalEtMA) generated four block copolymers, which were converted to amphiphilic structures by deprotection of the acetyl groups on the sugar units. Micelles with well-defined sizes of 26-50 nm were produced by self-assembly in water. The azobenzene units isomerised very rapidly to their more polar cis isomers under UV irradiation, reaching the photostationary state within 2 min, with reversion to the trans state taking several hours in the dark. This transition to the more polar cis state is an important criteria for aiding expulsion of a hydrophobic payload. In cell studies, unloaded micelles showed low cytotoxicity, and micelles loaded with the model hydrophobic compound Nile red demonstrated high cellular uptake in human melanoma A375 cells, demonstrating their suitability as a potential drug delivery system for melanoma. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:616 / 627
页数:12
相关论文
共 44 条
[1]  
Abd Karim KJ, 2014, POLYM CHEM
[2]   Aqueous RAFT Polymerization of N-Acryloylmorpholine, Synthesis of an ABA Triblock Glycopolymer and Study of its Self-Association Behavior [J].
Albertin, Luca ;
Wolnik, Anna ;
Ghadban, Ali ;
Dubreuil, Frederic .
MACROMOLECULAR CHEMISTRY AND PHYSICS, 2012, 213 (17) :1768-1782
[3]  
Babiuch K, 2014, ENCY POLYM SCI TECHN
[4]   Photoisomerization in different classes of azobenzene [J].
Bandara, H. M. Dhammika ;
Burdette, Shawn C. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (05) :1809-1825
[5]   Light-induced motions in azobenzene-containing polymers [J].
Cojocariu, C ;
Rochon, P .
PURE AND APPLIED CHEMISTRY, 2004, 76 (7-8) :1479-1497
[6]   Reversible photoisomerization of azobenzene-containing polymeric systems driven by visible light [J].
Dong, Ruijiao ;
Zhu, Bangshang ;
Zhou, Yongfeng ;
Yan, Deyue ;
Zhu, Xinyuan .
POLYMER CHEMISTRY, 2013, 4 (04) :912-915
[7]   Photo-responsive systems and biomaterials: photochromic polymers, light-triggered self-assembly, surface modification, fluorescence modulation and beyond [J].
Ercole, Francesca ;
Davis, Thomas P. ;
Evans, Richard A. .
POLYMER CHEMISTRY, 2010, 1 (01) :37-54
[8]   The generic enhancement of photochromic dye switching speeds in a rigid polymer matrix [J].
Evans, RA ;
Hanley, TL ;
Skidmore, MA ;
Davis, TP ;
Such, GK ;
Yee, LH ;
Ball, GE ;
Lewis, DA .
NATURE MATERIALS, 2005, 4 (03) :249-253
[9]   Galectin-3 in angiogenesis and metastasis [J].
Funasaka, Tatsuyoshi ;
Raz, Avraham ;
Nangia-Makker, Pratima .
GLYCOBIOLOGY, 2014, 24 (10) :886-891
[10]   Site-directed conjugation of "Clicked" glycopolymers to form glycoprotein mimics: Binding to mammalian lectin and induction of immunological function [J].
Geng, Jin ;
Mantovani, Giuseppe ;
Tao, Lei ;
Nicolas, Julien ;
Chen, Gaojian ;
Wallis, Russell ;
Mitchell, Daniel A. ;
Johnson, Benjamin R. G. ;
Evans, Stephen D. ;
Haddleton, David M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (49) :15156-15163